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Sinatra: The Chairman
One of the Best Books of the Year
The Washington Post - Los Angeles Times - Milwaukee Journal Sentinel
The story of Frank Sinatra's second act, Sinatra finds the Chairman on top of the world, riding high after an Oscar victory--and firmly reestablished as the top recording artist of his day. Following Sinatra from the mid-1950s to his death in 1998, Kaplan uncovers the man behind the myth, revealing by turns the peerless singer, the (sometimes) powerful actor, the business mogul, the tireless lover, and--of course--the close associate of the powerful and infamous. It was in these decades that the enduring legacy of Frank Sinatra was forged, and Kaplan vividly captures "Ol' Blue Eyes" in his later years. The sequel to the New York Times best-selling Frank, here is the concluding volume of the definitive biography of The Entertainer of the Century.
The Washington Post - Los Angeles Times - Milwaukee Journal Sentinel
The story of Frank Sinatra's second act, Sinatra finds the Chairman on top of the world, riding high after an Oscar victory--and firmly reestablished as the top recording artist of his day. Following Sinatra from the mid-1950s to his death in 1998, Kaplan uncovers the man behind the myth, revealing by turns the peerless singer, the (sometimes) powerful actor, the business mogul, the tireless lover, and--of course--the close associate of the powerful and infamous. It was in these decades that the enduring legacy of Frank Sinatra was forged, and Kaplan vividly captures "Ol' Blue Eyes" in his later years. The sequel to the New York Times best-selling Frank, here is the concluding volume of the definitive biography of The Entertainer of the Century.
992 pages, Hardcover
First published October 27, 2015
351 people are currently reading
1904 people want to read
About the author
James Kaplan
40 books91 followersJames Kaplan has been writing noted biography, journalism, and fiction for more than four decades. The author of Frank: The Voice and Sinatra: The Chairman, the definitive two-volume biography of Frank Sinatra, he has written more than one hundred major profiles of figures ranging from Miles Davis to Meryl Streep, from Arthur Miller to Larry David.
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Displaying 1 - 30 of 176 reviews
January 8, 2017
If I hear the narrator say, "ring a ding ding" one more time
Also, dear author, if you could stick to a timeline that would be great
I know I should probably rate this a 4 or even a 5 d/t its thoroughness, but I can't stand repetitiveness and confusion.
The book jumps right in at the nadir of his career, with Ava Gardner in the picture. There is no early life. Basically his recording and movie pursuits are discussed in great detail. His relationships with both incarnations of the infamous Rat Packs, all (I mean all) of his lady friends-because he was a whore, and his heated connection with the Kennedy family and various mafiosoes are all included.
This is an extremely long-winded book. It took me three days of heavy listening to finish. In the audio version each chapter is over an hour long, with over 20 chapters. Be prepared to dedicate yourself.
Also, dear author, if you could stick to a timeline that would be great
I know I should probably rate this a 4 or even a 5 d/t its thoroughness, but I can't stand repetitiveness and confusion.
The book jumps right in at the nadir of his career, with Ava Gardner in the picture. There is no early life. Basically his recording and movie pursuits are discussed in great detail. His relationships with both incarnations of the infamous Rat Packs, all (I mean all) of his lady friends-because he was a whore, and his heated connection with the Kennedy family and various mafiosoes are all included.
This is an extremely long-winded book. It took me three days of heavy listening to finish. In the audio version each chapter is over an hour long, with over 20 chapters. Be prepared to dedicate yourself.
December 15, 2015
A horror story. I couldn't stop reading this biography, and it is over 800 and something-like pages, and it strikes me as the ultimate American tale, and as its nightmare. Frank Sinatra, without over-stating, is without a doubt a great figure in American culture. He is also a monster. Nevertheless, a truly great pop(ular) artist who can cut through the bullshit by just singing. It is when he's not singing is when trouble lurks like a bad disease.
I read James Kaaplan's first volume, "Frank: The Voice, ' with incredible pleasure. What made the book sing out so greatly was Kaplan's ability to capture the early years of Sinatra and make the reader understand the world that he lived in, and the life of a big band vocalist. Also the author has a firm grip on the music itself, so it wasn't all just punches, drinking - there was also the music aspect of Sinatra's life. "Sinatra: The Chairman" is like an everlasting hang-over that never gets better.
It is interesting how Kaplan entitled these two parts of the biography. "Frank: The Voice" is very much an intimate read on one's music and character. He used the first name, and also brings up the subject matter of his instrument of choice - the voice. The second volume is his family name "Sinatra" and it is about power "The Chairman." And for me, this is what I find both interesting and troublesome about the second volume. First of all, I don't feel like it's the author's fault. I think the publisher or editor should have made this biography into three separate volumes. The early years (The Voice), then perhaps a book on the rest of the 1950s to the 1960s - and then perhaps the last volume could focus on his aging life. The thing is with Sinatra you can make just a book just on his relationship with the Mafia/Kennedy, or one focusing on his films, and it would be a fascinating individual read.
After reading "The Chairman" I feel like I was in a boxing match with Sinatra. This is a man who gave as well as obtained pain for himself. Not a long death mind you, but for sure he's a soul who got beaten up over and over again. I can't feel sorry for him, but I also feel really tired after finishing this book. It is sort of like taking care of a sick relative and they're driving you crazy, even though you love them. Frank Sinatra, was a total creep. A nice creep at times, and he had the moves of a person who had the social grace. But like someone who experiences life as if someone turned off and on the lights in one's house, he must have been a dangerous man to hang out with.
For me, when I listen to a classic Sinatra album, I'm totally lost in what he's saying to me at that moment when the needle hits the vinyl or I push the button on the CD player, or on my computer. He is one of the few singers, that I have to stop everything to listen to hm. His dictation or voice makes me follow the lyrics. He is probably one of the great American vocalists, where the lyrics are front and center. It is never lost in the mix of the recording. The wording is so important to his aesthetic. He had taste, and he understood the concept of the recording, so therefore he had a vision as well. This has nothing to do with his cruelty in his private life whatsoever. Nor do I think it has anything to do with his personal relationships. He comes upon a song, and bingo, he can express the full emotional aspect of that piece.
When I hear a Sinatra recording, I'm not thinking of the Mafia, his women, or anything in his life. I'm listening to someone who can articulate a certain joy or pain, that I can easily identify with. As a listener, I can't imagine myself as a jet-setting playboy, but I too know the stings and joy of love, and that is what is so masterful regarding Sinatra's talents. The noise of his private life is just that, noise. Of course, he had a fascinating life. The media is so psychotic and Sinatra had the misfortune (or talent) to feed that engine that never tired.
The problem of dealing with Sinatra's 100th birthday is that we are kind of forced to take his whole package. Therefore we can comment on his lifestyle and cruelty, and that somehow makes his art less appealing. Which is understandable, but the fact is he was a fantastic participant in record / music making, and that is what we should remember him for. The mid-life crisis that is the Rat Pack, his moronic relationship with certain girlfriends and male friends alike - all are interesting. But when I play a good Sinatra record, I totally forget all of that, and fall into the mist or landscape that is a combination of magic and vision. Sinatra had the ability to transform the listener, and that is what I like to remember him by.
"The Voice" and "The Chairman" is surely the last of the biographies on this gigantic figure. If you want to know who this man is, was, and his role in pop culture, these books will lead you to that path. On the other hand, I would recommend the Capital and some of the Reprise label material, that really addresses his importance to pop culture.
I read James Kaaplan's first volume, "Frank: The Voice, ' with incredible pleasure. What made the book sing out so greatly was Kaplan's ability to capture the early years of Sinatra and make the reader understand the world that he lived in, and the life of a big band vocalist. Also the author has a firm grip on the music itself, so it wasn't all just punches, drinking - there was also the music aspect of Sinatra's life. "Sinatra: The Chairman" is like an everlasting hang-over that never gets better.
It is interesting how Kaplan entitled these two parts of the biography. "Frank: The Voice" is very much an intimate read on one's music and character. He used the first name, and also brings up the subject matter of his instrument of choice - the voice. The second volume is his family name "Sinatra" and it is about power "The Chairman." And for me, this is what I find both interesting and troublesome about the second volume. First of all, I don't feel like it's the author's fault. I think the publisher or editor should have made this biography into three separate volumes. The early years (The Voice), then perhaps a book on the rest of the 1950s to the 1960s - and then perhaps the last volume could focus on his aging life. The thing is with Sinatra you can make just a book just on his relationship with the Mafia/Kennedy, or one focusing on his films, and it would be a fascinating individual read.
After reading "The Chairman" I feel like I was in a boxing match with Sinatra. This is a man who gave as well as obtained pain for himself. Not a long death mind you, but for sure he's a soul who got beaten up over and over again. I can't feel sorry for him, but I also feel really tired after finishing this book. It is sort of like taking care of a sick relative and they're driving you crazy, even though you love them. Frank Sinatra, was a total creep. A nice creep at times, and he had the moves of a person who had the social grace. But like someone who experiences life as if someone turned off and on the lights in one's house, he must have been a dangerous man to hang out with.
For me, when I listen to a classic Sinatra album, I'm totally lost in what he's saying to me at that moment when the needle hits the vinyl or I push the button on the CD player, or on my computer. He is one of the few singers, that I have to stop everything to listen to hm. His dictation or voice makes me follow the lyrics. He is probably one of the great American vocalists, where the lyrics are front and center. It is never lost in the mix of the recording. The wording is so important to his aesthetic. He had taste, and he understood the concept of the recording, so therefore he had a vision as well. This has nothing to do with his cruelty in his private life whatsoever. Nor do I think it has anything to do with his personal relationships. He comes upon a song, and bingo, he can express the full emotional aspect of that piece.
When I hear a Sinatra recording, I'm not thinking of the Mafia, his women, or anything in his life. I'm listening to someone who can articulate a certain joy or pain, that I can easily identify with. As a listener, I can't imagine myself as a jet-setting playboy, but I too know the stings and joy of love, and that is what is so masterful regarding Sinatra's talents. The noise of his private life is just that, noise. Of course, he had a fascinating life. The media is so psychotic and Sinatra had the misfortune (or talent) to feed that engine that never tired.
The problem of dealing with Sinatra's 100th birthday is that we are kind of forced to take his whole package. Therefore we can comment on his lifestyle and cruelty, and that somehow makes his art less appealing. Which is understandable, but the fact is he was a fantastic participant in record / music making, and that is what we should remember him for. The mid-life crisis that is the Rat Pack, his moronic relationship with certain girlfriends and male friends alike - all are interesting. But when I play a good Sinatra record, I totally forget all of that, and fall into the mist or landscape that is a combination of magic and vision. Sinatra had the ability to transform the listener, and that is what I like to remember him by.
"The Voice" and "The Chairman" is surely the last of the biographies on this gigantic figure. If you want to know who this man is, was, and his role in pop culture, these books will lead you to that path. On the other hand, I would recommend the Capital and some of the Reprise label material, that really addresses his importance to pop culture.
October 21, 2015
While it is tempting to look behind the façade of an artist and their work, I think it is always inadvisable. What one sees is rarely appealing, is what I've learned from experience, and that is very much the case with Frank Sinatra, who was psychologically unwell, despite being artistically exceptional. The biggest understatement in this book is when the author states that Sinatra had a: "complex and contradictory soul".
If you are so brave or so foolish to want to see Sinatra more clearly, and you don't want to be too disappointed, then the two doorstops by this author could be the answer: Frank: The Voice, and Sinatra: The Chairman. He cleans up the real Sinatra quite a bit, quoting mainly from other people's books, making the portrayed figure someone who might have a wider appeal than the really-real Sinatra, who came to life through the words of the star's valet, George Jacobs.
Jacobs wrote My Life with Frank Sinatra, which offered the rough-truth: vulgar-laden speech, sexual sleaze, alcohol problems, sadistic behavior, criminal behavior, masochistic behavior, racist speech, emotional disturbances, psychological disturbances, and a Jekyll and Hyde character that could veer into violence. The big sleaze factor of the man's life leaves the reader with a dirty feeling.
I had that same dirty feeling while reading this book, Sinatra: The Chairman, since despite the author's attempts to water down the truth with this mild hagiography, the real man shone through. I wanted to bathe after each reading session. The early sections feel of the book feel a bit more balanced than the later sections, where the author seems to try to explain and excuse away some of the un-explainable and inexcusable behavior by the star.
The crimes alone that the man committed and got away with due to his wealth and celebrity status (perjury, assault and battery, breaking and entering, hiring thugs to quite possibly murder someone, and certainly to beat up people) were enough to make me cringe whenever I hear his name now, especially thinking about the rape that is in the book, that the star paid off with a hundred bucks.
Sinatra: The Chairman is divided into five sections that include timeline overlaps, which I found to be confusing at times:
The Whirlwind (12 years)
The Chairman
Midas
Furies
The Late Show
I would have loved a book that covered only the creative sessions for the beautiful music Sinatra produced, and skipped everything else, since the analyses of the recording sessions, choice of songs, arrangements, and albums, were truly fascinating. The film studies felt overdone considering the fact that most of Sinatra's films were not so great, in my humble opinion. I found the life studies depressing for their portrayal of a man I would never want to even be in the same room with.
The harshest notes in the book are reserved for Sinatra's last wife, Barbara Marx. What the author did not point out, however, was that when you spend your psychologically disturbed life using woman and discarding them, the only kind of woman you're likely to end up with is one who is with you for financial security.
Actually, from how the author describes Sinatra, it makes sense that he married a gold-digger, since he would have only trusted a relationship in which he held all the power firmly in his hands, or more specifically, in his bank accounts.
If you can stand the sleaze, there are lots of anecdotes in Sinatra: The Chairman about the man's fits of rage, relationships, ambitions, traumas, crimes, and so on. With the pseudo-psychological analysis that the book offers for a man who clearly needed a real psychological analysis and treatment, the author stresses repeatedly that: "Constant activity was a balm to Sinatra's ferocious impatience, his tenor of boredom and solitude."
Please visit my full and illustrated review at Italophile Book Reviews. I received a review-copy of the book. This is my honest review.
http://italophilebookreviews.blogspot...
If you are so brave or so foolish to want to see Sinatra more clearly, and you don't want to be too disappointed, then the two doorstops by this author could be the answer: Frank: The Voice, and Sinatra: The Chairman. He cleans up the real Sinatra quite a bit, quoting mainly from other people's books, making the portrayed figure someone who might have a wider appeal than the really-real Sinatra, who came to life through the words of the star's valet, George Jacobs.
Jacobs wrote My Life with Frank Sinatra, which offered the rough-truth: vulgar-laden speech, sexual sleaze, alcohol problems, sadistic behavior, criminal behavior, masochistic behavior, racist speech, emotional disturbances, psychological disturbances, and a Jekyll and Hyde character that could veer into violence. The big sleaze factor of the man's life leaves the reader with a dirty feeling.
I had that same dirty feeling while reading this book, Sinatra: The Chairman, since despite the author's attempts to water down the truth with this mild hagiography, the real man shone through. I wanted to bathe after each reading session. The early sections feel of the book feel a bit more balanced than the later sections, where the author seems to try to explain and excuse away some of the un-explainable and inexcusable behavior by the star.
The crimes alone that the man committed and got away with due to his wealth and celebrity status (perjury, assault and battery, breaking and entering, hiring thugs to quite possibly murder someone, and certainly to beat up people) were enough to make me cringe whenever I hear his name now, especially thinking about the rape that is in the book, that the star paid off with a hundred bucks.
Sinatra: The Chairman is divided into five sections that include timeline overlaps, which I found to be confusing at times:
The Whirlwind (12 years)
The Chairman
Midas
Furies
The Late Show
I would have loved a book that covered only the creative sessions for the beautiful music Sinatra produced, and skipped everything else, since the analyses of the recording sessions, choice of songs, arrangements, and albums, were truly fascinating. The film studies felt overdone considering the fact that most of Sinatra's films were not so great, in my humble opinion. I found the life studies depressing for their portrayal of a man I would never want to even be in the same room with.
The harshest notes in the book are reserved for Sinatra's last wife, Barbara Marx. What the author did not point out, however, was that when you spend your psychologically disturbed life using woman and discarding them, the only kind of woman you're likely to end up with is one who is with you for financial security.
Actually, from how the author describes Sinatra, it makes sense that he married a gold-digger, since he would have only trusted a relationship in which he held all the power firmly in his hands, or more specifically, in his bank accounts.
If you can stand the sleaze, there are lots of anecdotes in Sinatra: The Chairman about the man's fits of rage, relationships, ambitions, traumas, crimes, and so on. With the pseudo-psychological analysis that the book offers for a man who clearly needed a real psychological analysis and treatment, the author stresses repeatedly that: "Constant activity was a balm to Sinatra's ferocious impatience, his tenor of boredom and solitude."
Please visit my full and illustrated review at Italophile Book Reviews. I received a review-copy of the book. This is my honest review.
http://italophilebookreviews.blogspot...
September 10, 2025
Volume II of this monumental work by James Kaplan picks up with Frank Sinatra basking in the glow of his Academy Award for Best Supporting Actor in From Here To Eternity. This marks the beginning of Sinatra's almost-miraculous comeback from near-oblivion. Suddenly he was amassing great power in both the recording and film industries (he never really found success on TV despite several half-hearted attempts). Sinatra would become such a dominant figure on both coasts and in American life that he openly associated with mobsters and almost flaunted his bad-boy behavior.
And there was plenty of that. Even more so than Volume I, this book is chock full of Sinatra's excesses (drinking, smoking, sex, extravagant spending, physical assaults). Normally surrounded by a phalanx of burly bodyguards, Sinatra became almost untouchable wherever he went. His known associations with Mafia figures such as Sam Giancana caused him much ill press and caused the FBI to use up a lot paper, but Sinatra dared anyone to do something to him. He did eventually pay a price for those ill-conceived relationships - both business and pleasure - when he was forced to give up his ownership stake in the Cal-Neva Lodge. Sinatra, by association, ran afoul of the Nevada Gaming Control Board.
While we are on the Mob and the Mafia, the question needs to be asked: why would someone as famous and as wealthy as Sinatra jeopardize his career (and possibly his life) by proudly associating with gangsters? I think he was enticed by the recklessness and power that those people wielded; that they could do almost whatever they wanted to whoever they wanted whenever they wanted, and most of the time they got away with it. Which is how Sinatra also lived his life. Sinatra had a short fuse, and he would blow at the slightest sign of disrespect - or just because he felt like it. So he liked to be around people who acted like he did.
Sinatra had run-ins with just about everyone at some point or another. He had zero qualms about cutting someone out of his life. He did this with one of his earliest friends and supporters, Hank Sanicola (leaving him stranded on a desert highway, having kicked him out of his car after Sanicola questioned him too much about his casino activities in Las Vegas). He also did this to his longtime black valet, George Jacobs (whom he called "Spook" and threw food at if it wasn't prepared to his liking) by having the locks changed on his house. Outside of his family, if you were not of use to him, you were for all intents and purposes not alive in his mind. Outside of fellow stars, and the aforementioned Mafia types, Sinatra surrounded himself with mostly sycophants who would do what he wanted while putting up with his verbal abuse. Anyone with the temerity to push back was exiled - usually for life.
Here is an example of Sinatra's atrocious behavior, from pages 324-325, involving John Wayne:
"After the party broke up, in the early hours of Saturday, May 14, Frank, somewhat worse for the wear, headed out to the parking lot with Sammy Davis's bodyguard.... There Frank spotted John Wayne, whose recent public critique of his hiring of Albert Maltz was still fresh in his mind. ..Frank... stalked up to Wayne... and stood squarely in the much larger actor's path.
'You seem to disagree with me,' Frank said....
But John Wayne, to his credit, spoke conciliatorily. 'Now, now, Frank, we can discuss this somewhere else,' he said.
At this point, though both principals later denied it, a witness (a reporter for the Los Angeles Herald-Express), said that Frank shoved Wayne and that Wayne shoved him back. Friends separated them; Wayne walked away...
Still steaming, Frank stepped - whether intentionally or not isn't clear - into the path of a moving car being driven by a parking lot attendant named Clarence English. The car screeched to a stop. 'Hey, Charley!' Sinatra yelled. 'You almost hit me! You know what I'm insured for?'
English shook his head, and Frank raced around to his side of the car. 'Can you fight? You'd better be able to,' he said to the attendant. He reached for English through the driver's window, and another attendant, twenty-one-year-old Edward Moran, remonstrated with him, 'Aw, Frank, he wasn't trying to hit you with the car. He's only trying to make a living.'
'Who the fuck are you?' Frank said and pushed Moran, who then made the mistake of trying to defend himself, striking Frank.
Big John Hopkins stepped in and began raining blows on Moran, while Sinatra... danced up and down, shouting, 'Tell that guy not to sue me if he knows what's good for him! I'll break both his legs!'
Moran, who was treated for facial cuts and bruises, disobeyed Frank's order, bringing a $100,000 suit against him for violent assault. Sinatra settled out of court."
This is just one example in an 883 page book that has more pages than not with escapades such as that. Sinatra was simply out of control, and became so powerful that nobody dared to stand up to him. Or else something like the above occurred.
Politically, Sinatra was still a Democrat when the books picks up his story. He tries to form a friendship with John F. Kennedy in the 1950s, partly through his father Joseph P. Kennedy. JFK did hang out with Sinatra a few times, but as he rose to prominence Sinatra's mob associations and unruly behavior became increasingly unwelcome in the Kennedy camp. It did not help that Jackie hated him. It also did not help that Sinatra called JFK - even after he was elected President - "Chickie baby" or "Prez". Needless to say, JFK did to Sinatra what Sinatra did to others: cut him off. Sinatra blamed Bobby Kennedy for this more than anyone else, and opposed him immeasurably until the latter's assassination in 1968.
Speaking of 1968, Sinatra fostered a friendship with Hubert Humphrey, and did some campaigning for him that year before being sidelined; again, the gambling and mob connections, and the voluble personal behavior, came back to bite Sinatra. So these "slights", as Sinatra thought of them, and his growing comfortableness with the Old Guard of Hollywood and New York, gradually turned Sinatra rightward in his politics. Sinatra initially could not stand either Richard Nixon nor Ronald Reagan, yet came to perform at one of the presidential inaugurations for both men, and became friends with them. Once again, he was attracted to power.
Kaplan also discusses at length Sinatra's astounding recording career, going through all of his albums and singles. Kaplan is really good here as a music critic for the reader: he explains what songs work (like "My Way") and why, and which songs and/or albums do not work. He chronicles Sinatra's growing frustration with Rock N Roll, his dislike of bands such as The Beatles, and how he increasingly tried to change his style, with limited results.
Ditto for Sinatra's movie career. There seemed to me to be a lot more duds than hits. Kaplan reviews The Rat Pack movies, and also discusses the mythology surrounding the players involved (Sinatra, Dean Martin, Sammy Davis Jr, Joey Bishop, Peter Lawford). He also writes about how bad the movies were, and how unexceptional Sinatra was in many of his movies. Unlike his recordings, where he would painstakingly do take after take after take of a song until he and the orchestra got it to his exacting specifications, with acting Sinatra wanted to do one take only and leave. Only in a few films did he not do this, one of them being "The Manchurian Candidate" in 1962.
Sinatra's weird marriage to Mia Farrow was also covered. Talk about a mismatch from the start. He was twenty-nine years older than her. It didn't last long. His last marriage was to someone whom Kaplan portrays as a gold digger. It seems that as he aged Sinatra knew he couldn't have a lasting intimate relationship with anyone, and just accepted Barbara Marx as someone who would look after him.
At page 600, we were only in 1965, just a little over a decade from events at the beginning of the book. I began to wonder if Kaplan was going to do one of those jobs where the author hurries up near the end of someone's life and seems to tire of their subject. My concerns were not valid. Sinatra retired in 1971, then came out of retirement a year and a half later, but his output was nowhere near what it had been before. He almost completely stopped acting, and only put out records occasionally, and those were met with mixed success. So there was not nearly as much to write about.
Also, Sinatra started to fail physically a good decade plus before his 1998 death. He began having vision and hearing problems, then some memory issues. And, the way he lived his life was finally catching up with him. Decades of heavy drinking (a bottle of Jack Daniels was put inside his funeral casket with his body) and smoking a couple of packs of unfiltered Camel cigarettes on a daily basis took their toll. Sinatra traveled the world doing mega-concerts until the early 1990s. Then he basically spent the last four years of his life at home, waiting to die. Normally, I would feel bad for someone when that happens to them. But Sinatra had been so horrible to so many people for most of his life, that his failing health did not register any sympathy from me.
Thankfully this wonderful book did register with me. You do not have to like Sinatra nor his music to enjoy reading about his fascinating life. Kaplan is exceedingly neutral on Sinatra throughout both books, striving to treat him fairly. That said, after 718 pages in the first volume, and 883 pages in this one (not including notes), I am glad to be done with Sinatra.
Grade: A
And there was plenty of that. Even more so than Volume I, this book is chock full of Sinatra's excesses (drinking, smoking, sex, extravagant spending, physical assaults). Normally surrounded by a phalanx of burly bodyguards, Sinatra became almost untouchable wherever he went. His known associations with Mafia figures such as Sam Giancana caused him much ill press and caused the FBI to use up a lot paper, but Sinatra dared anyone to do something to him. He did eventually pay a price for those ill-conceived relationships - both business and pleasure - when he was forced to give up his ownership stake in the Cal-Neva Lodge. Sinatra, by association, ran afoul of the Nevada Gaming Control Board.
While we are on the Mob and the Mafia, the question needs to be asked: why would someone as famous and as wealthy as Sinatra jeopardize his career (and possibly his life) by proudly associating with gangsters? I think he was enticed by the recklessness and power that those people wielded; that they could do almost whatever they wanted to whoever they wanted whenever they wanted, and most of the time they got away with it. Which is how Sinatra also lived his life. Sinatra had a short fuse, and he would blow at the slightest sign of disrespect - or just because he felt like it. So he liked to be around people who acted like he did.
Sinatra had run-ins with just about everyone at some point or another. He had zero qualms about cutting someone out of his life. He did this with one of his earliest friends and supporters, Hank Sanicola (leaving him stranded on a desert highway, having kicked him out of his car after Sanicola questioned him too much about his casino activities in Las Vegas). He also did this to his longtime black valet, George Jacobs (whom he called "Spook" and threw food at if it wasn't prepared to his liking) by having the locks changed on his house. Outside of his family, if you were not of use to him, you were for all intents and purposes not alive in his mind. Outside of fellow stars, and the aforementioned Mafia types, Sinatra surrounded himself with mostly sycophants who would do what he wanted while putting up with his verbal abuse. Anyone with the temerity to push back was exiled - usually for life.
Here is an example of Sinatra's atrocious behavior, from pages 324-325, involving John Wayne:
"After the party broke up, in the early hours of Saturday, May 14, Frank, somewhat worse for the wear, headed out to the parking lot with Sammy Davis's bodyguard.... There Frank spotted John Wayne, whose recent public critique of his hiring of Albert Maltz was still fresh in his mind. ..Frank... stalked up to Wayne... and stood squarely in the much larger actor's path.
'You seem to disagree with me,' Frank said....
But John Wayne, to his credit, spoke conciliatorily. 'Now, now, Frank, we can discuss this somewhere else,' he said.
At this point, though both principals later denied it, a witness (a reporter for the Los Angeles Herald-Express), said that Frank shoved Wayne and that Wayne shoved him back. Friends separated them; Wayne walked away...
Still steaming, Frank stepped - whether intentionally or not isn't clear - into the path of a moving car being driven by a parking lot attendant named Clarence English. The car screeched to a stop. 'Hey, Charley!' Sinatra yelled. 'You almost hit me! You know what I'm insured for?'
English shook his head, and Frank raced around to his side of the car. 'Can you fight? You'd better be able to,' he said to the attendant. He reached for English through the driver's window, and another attendant, twenty-one-year-old Edward Moran, remonstrated with him, 'Aw, Frank, he wasn't trying to hit you with the car. He's only trying to make a living.'
'Who the fuck are you?' Frank said and pushed Moran, who then made the mistake of trying to defend himself, striking Frank.
Big John Hopkins stepped in and began raining blows on Moran, while Sinatra... danced up and down, shouting, 'Tell that guy not to sue me if he knows what's good for him! I'll break both his legs!'
Moran, who was treated for facial cuts and bruises, disobeyed Frank's order, bringing a $100,000 suit against him for violent assault. Sinatra settled out of court."
This is just one example in an 883 page book that has more pages than not with escapades such as that. Sinatra was simply out of control, and became so powerful that nobody dared to stand up to him. Or else something like the above occurred.
Politically, Sinatra was still a Democrat when the books picks up his story. He tries to form a friendship with John F. Kennedy in the 1950s, partly through his father Joseph P. Kennedy. JFK did hang out with Sinatra a few times, but as he rose to prominence Sinatra's mob associations and unruly behavior became increasingly unwelcome in the Kennedy camp. It did not help that Jackie hated him. It also did not help that Sinatra called JFK - even after he was elected President - "Chickie baby" or "Prez". Needless to say, JFK did to Sinatra what Sinatra did to others: cut him off. Sinatra blamed Bobby Kennedy for this more than anyone else, and opposed him immeasurably until the latter's assassination in 1968.
Speaking of 1968, Sinatra fostered a friendship with Hubert Humphrey, and did some campaigning for him that year before being sidelined; again, the gambling and mob connections, and the voluble personal behavior, came back to bite Sinatra. So these "slights", as Sinatra thought of them, and his growing comfortableness with the Old Guard of Hollywood and New York, gradually turned Sinatra rightward in his politics. Sinatra initially could not stand either Richard Nixon nor Ronald Reagan, yet came to perform at one of the presidential inaugurations for both men, and became friends with them. Once again, he was attracted to power.
Kaplan also discusses at length Sinatra's astounding recording career, going through all of his albums and singles. Kaplan is really good here as a music critic for the reader: he explains what songs work (like "My Way") and why, and which songs and/or albums do not work. He chronicles Sinatra's growing frustration with Rock N Roll, his dislike of bands such as The Beatles, and how he increasingly tried to change his style, with limited results.
Ditto for Sinatra's movie career. There seemed to me to be a lot more duds than hits. Kaplan reviews The Rat Pack movies, and also discusses the mythology surrounding the players involved (Sinatra, Dean Martin, Sammy Davis Jr, Joey Bishop, Peter Lawford). He also writes about how bad the movies were, and how unexceptional Sinatra was in many of his movies. Unlike his recordings, where he would painstakingly do take after take after take of a song until he and the orchestra got it to his exacting specifications, with acting Sinatra wanted to do one take only and leave. Only in a few films did he not do this, one of them being "The Manchurian Candidate" in 1962.
Sinatra's weird marriage to Mia Farrow was also covered. Talk about a mismatch from the start. He was twenty-nine years older than her. It didn't last long. His last marriage was to someone whom Kaplan portrays as a gold digger. It seems that as he aged Sinatra knew he couldn't have a lasting intimate relationship with anyone, and just accepted Barbara Marx as someone who would look after him.
At page 600, we were only in 1965, just a little over a decade from events at the beginning of the book. I began to wonder if Kaplan was going to do one of those jobs where the author hurries up near the end of someone's life and seems to tire of their subject. My concerns were not valid. Sinatra retired in 1971, then came out of retirement a year and a half later, but his output was nowhere near what it had been before. He almost completely stopped acting, and only put out records occasionally, and those were met with mixed success. So there was not nearly as much to write about.
Also, Sinatra started to fail physically a good decade plus before his 1998 death. He began having vision and hearing problems, then some memory issues. And, the way he lived his life was finally catching up with him. Decades of heavy drinking (a bottle of Jack Daniels was put inside his funeral casket with his body) and smoking a couple of packs of unfiltered Camel cigarettes on a daily basis took their toll. Sinatra traveled the world doing mega-concerts until the early 1990s. Then he basically spent the last four years of his life at home, waiting to die. Normally, I would feel bad for someone when that happens to them. But Sinatra had been so horrible to so many people for most of his life, that his failing health did not register any sympathy from me.
Thankfully this wonderful book did register with me. You do not have to like Sinatra nor his music to enjoy reading about his fascinating life. Kaplan is exceedingly neutral on Sinatra throughout both books, striving to treat him fairly. That said, after 718 pages in the first volume, and 883 pages in this one (not including notes), I am glad to be done with Sinatra.
Grade: A
December 12, 2024
Sinatra was quite a shitbag
November 16, 2015
This bio, which goes from 1954 when Sinatra won an Oscar to his death, is a mixed bag. The first two-thirds are filled with interesting details about the man, his affairs, his movies and especially his music. Almost every album he made from '54 to '70 is covered in meticulous detail--occasionally it starts to feel like too much detail, but ultimately the sections on the music are the best things in the book. Kaplan makes Sinatra come alive and tries to give a balanced view of a man who could be a generous and kind friend but who could turn a dime (often for petty reasons) and become a ruthless enemy. But after 1970, the book falls off quite a ways. Perhaps Kaplan ran out of sources or was just bored with Sinatra's output from '70 through the mid 90s, but the book really grinds to a halt. Even the important Duets album of the mid 90s gets only one paragraph with no mention at all of its followup. Much of this is compelling reading, but ultimately it disappoints.
September 26, 2019
"I don’t know what other singers feel when they articulate lyrics, but being an 18-karat manic-depressive and having lived a life of violent emotional contradictions, I have an over-acute capacity for sadness as well as elation. I know what the cat who wrote the song is trying to say. I’ve been there—and back. I guess the audience feels it along with me. They can’t help it. Sentimentality, after all, is an emotion common to all humanity."
June 16, 2024
This book is so large it has taken me forever to finish it. I have, however, actually enjoyed every part of it! This is the most comprehensive biography I’ve ever read and it is full of interesting facts, stories, and even lots of background information on just about everyone in the life of Frank. The book covers movies, music, presidential elections, the mob, and much more. While the ‘final act’ of the book and Franks life does move at a quicker pace than all previous parts of the book, it is a gentle reminder that even the most recognizable, powerful, and talented people in the world come to an end like the rest of us. This biography painted a picture of who Frank Sinatra was and who he wanted to be. You can tell this was a long labor of love for James Kaplan and he hit it out of the park. 5 stars purely for telling a great story, well written, and engaging until the end.
December 21, 2015
Exhaustive and complete, this will be the definitive Sinatra biography for years to come. What places this (and Frank: The Voice, the first volume) above all others is that it actually speaks in some depth about the artistry of Sinatra, rather than just the lurid details. What is it about these recordings and the technique of the singer that stands above all others? What is complete as well (but sometimes too completely covered) are the personal details too often covered by other tabloid biographies. While this is welcome, the 883 pages of narrative could be probably do with having 100-200 pages of mafia connections and endless liaisons with women covered in detail. Nonetheless, a splendid exploration of the man in all his genius and his messy details.
December 8, 2020
Sinatra's era was before my time as a adult, so consequently he impacted on my parents more than me. I was a witness to that time in history when starts from Hollywood were glorified, revered and idolized. This book provides insight to one of these demigods - Frank Sinatra. His love life is opened up for all to see. From Ava Gardner to Gloria Vanderbilt, to a bevy of others. Fame can get you what you want it seems. There is no doubt he was a masterful singer. One of the greatest ! As a movie star, he probably shone owing to his status within the Hollywood crowd. As he came from New York, his mob connections were well documented but only because they loved the guy and having their umbrella of influence got him notoriety. It was a time when characters like Sinatra were bigger than life. In fact when Hollywood and Vegas were in the spotlight you had to have the draws. He was one of the biggest ! The book allows you to go down memory lane with all the actors, actresses, singers, songwriters, as a child growing up that took center stage. So from this angle it allowed me to reminisce about the names , the songs and the the films that impacted me during those informative years. I would have liked to have said that I read the book word by word, but because there were lots of repetitive and perhaps redundant parts I did find myself skimming at times. All and all a decent read, but I caution one, the actual book is heavy so pump some iron if you plan on taking it to the beach or on a plane
August 29, 2025
Amazing, this 35 CD audiobook. After my business day, I would flop on my bed and listen to two or three CDs. Easy way to unwind. Nice to not have to read. Soothing.
It was a pleasant weaving of 20th century entertainment history, James Kaplan's flowing wordsmithing and the dulcet tones of narrator Donald Corren that breezed away these 41 hours of biography.
Kaplan blends Sinatra's talent, personality with the crazy quilt of larger-than-life characters into a part pop culture, part psychology fun romp.
The author also picks apart the song lyrics of many of the hit songs. That promotes better listening to these golden standards.
I was sorry when I finished.
It was a pleasant weaving of 20th century entertainment history, James Kaplan's flowing wordsmithing and the dulcet tones of narrator Donald Corren that breezed away these 41 hours of biography.
Kaplan blends Sinatra's talent, personality with the crazy quilt of larger-than-life characters into a part pop culture, part psychology fun romp.
The author also picks apart the song lyrics of many of the hit songs. That promotes better listening to these golden standards.
I was sorry when I finished.
February 26, 2021
So this is a very detailed account of the life of Sinatra starting at the mid point in his 40s. The detail, was often times a bit tedious. The main problem I have with this book is the complete lack of a timeline. There absolutely is none. It was frustrating through the first 15% or so until I learned Kaplan didn't have a timeline in mind. He jumps around like a kid on a trampoline.
September 25, 2015
With Frank Sinatra: The Chairman, author James Kaplan has proven himself an expert biographer as he presents an in-depth look into not only Frank Sinatra, the singer and actor, but also Frank Sinatra, the man behind the multifaceted talents. Focusing a great deal on the mid- to late- 1950's, Kaplan reveals a side of Sinatra that many may not be familiar with (at least for this reader anyway). Behind the talent and fame, Frank Sinatra always felt like the insecure little boy from Hoboken, New Jersey trying to compete with "Big Boys". It's this insecurity and desire to rise above the rest that ultimately became the driving force behind Sinatra in all aspects of business and life. During the 1950's, Sinatra often worked on more than one movie at a time while still spending the wee hours of the mornings in a recording studio. Kaplan's thorough research and knowledge, reveals Sinatra's sense of tenacity where his music was concerned and how he would meticulously work on one arrangement until he achieved that perfect sound. It was also during this same period that Sinatra struggled with his failing marriage to Ava Gardner which became a source of immense grief. From the recording studios to Hollywood movie sets, Kaplan opens the door to allow the reader to travel back in time and to rub elbows with some of the biggest names of the period. Kaplan's writing is not only thorough and well-researched, but one that is also interwoven with an immense amount of integrity unlike previous Sinatra biographers over the years. Although I was rather intimated by this massive 992-page look into the life of Frank Sinatra, this was one of the best biographies I have read in quite some time and one that I would HIGHLY recommend to Sinatra fans, both young and old alike. FIVE stars!
September 13, 2015
I received a prepublication copy of this book (October 27, 2015) through NetGalley with the understanding that I would publish are review on my blog, LinkedIn, Facebook, Twitter and Google + pages along with NetGalley, Amazon and Goodreads.
I requested this book because I am have long enjoyed listening to his music. This is the first biography about him that I have read and also the first book by James Kaplan that I have read.
This book covers the second half of Frank Sinatra's life starting right after he received the Best Supporting Actor Oscar for "From Here to Eternity". The author focuses primarily on the late 50's, 60's and the early 70's. The last two decades of his life are given a once over lightly in a few chapters.
The book is an interesting read primarily because I have not read any others about Sinatra. The writing style is alright, but the author does tend to be repetitive at times especially when describing individuals or events more than once. He does cover the man - warts and all. He also does not declare some "facts" to be true as other authors have (primarily Kitty Kelly) due to them being hearsay or the fact that there are conflicting stories told about the event.
I most enjoyed the detail given to the events surrounding his recording sessions in the late 50's and early 60's. It gave me a new appreciation to the songs as I listened to them while reading the book.
I recommend this book to anyone who has an interest in learning more about the last half of Frank Sinatra's life.
I requested this book because I am have long enjoyed listening to his music. This is the first biography about him that I have read and also the first book by James Kaplan that I have read.
This book covers the second half of Frank Sinatra's life starting right after he received the Best Supporting Actor Oscar for "From Here to Eternity". The author focuses primarily on the late 50's, 60's and the early 70's. The last two decades of his life are given a once over lightly in a few chapters.
The book is an interesting read primarily because I have not read any others about Sinatra. The writing style is alright, but the author does tend to be repetitive at times especially when describing individuals or events more than once. He does cover the man - warts and all. He also does not declare some "facts" to be true as other authors have (primarily Kitty Kelly) due to them being hearsay or the fact that there are conflicting stories told about the event.
I most enjoyed the detail given to the events surrounding his recording sessions in the late 50's and early 60's. It gave me a new appreciation to the songs as I listened to them while reading the book.
I recommend this book to anyone who has an interest in learning more about the last half of Frank Sinatra's life.
October 18, 2020
"We'll do it my way, or you can fuck off."
As I said in my review of Volume I, there is nothing really more quintessentially American than Frank Sinatra. The second volume picks up right where the first one left off, Sinatra, heady after his Oscar win and over the next 900+ pages charts his wandering career up until basically the early 80s when he became, bizarrely a staunch Reaganite conservative, a complete, baffling about-face.
As with the preceding book, this is not just a comprehensive biography of Sinatra, his assholery, charm, and unassailable art, but because Sinatra was such a key cultural figure for the second half of the 20th century, it is just as much a biography of the times as well. Sinatra womanized with JFK, hung out with the Mob, basically created what we now think of as the Vegas That Was (there's even good bits on how Sin City got ruined and Disneyfied), hung out with George Harrison, married Mia Farrow, formed the Rat Pack, and so on and so on. Thus, there's a lot to dig into here and you'll get a different perspective on those times through the experiences, dickish or otherwise. My only complaint is that the later years get squashed into a very slim part of the book and ran through pretty quickly. I'd liked to have learned more about ailing Frank, his relationship with his sometimes distant children, and his tenacious hold on music up until the very end.
As I said in my review of Volume I, there is nothing really more quintessentially American than Frank Sinatra. The second volume picks up right where the first one left off, Sinatra, heady after his Oscar win and over the next 900+ pages charts his wandering career up until basically the early 80s when he became, bizarrely a staunch Reaganite conservative, a complete, baffling about-face.
As with the preceding book, this is not just a comprehensive biography of Sinatra, his assholery, charm, and unassailable art, but because Sinatra was such a key cultural figure for the second half of the 20th century, it is just as much a biography of the times as well. Sinatra womanized with JFK, hung out with the Mob, basically created what we now think of as the Vegas That Was (there's even good bits on how Sin City got ruined and Disneyfied), hung out with George Harrison, married Mia Farrow, formed the Rat Pack, and so on and so on. Thus, there's a lot to dig into here and you'll get a different perspective on those times through the experiences, dickish or otherwise. My only complaint is that the later years get squashed into a very slim part of the book and ran through pretty quickly. I'd liked to have learned more about ailing Frank, his relationship with his sometimes distant children, and his tenacious hold on music up until the very end.
May 2, 2017
I highly recommend the Kaplan series on Frank Sinatra, this is the second part of Frank's life and even more packed than the first. I think what Kaplan is able to capture in a better way than most biographers is the true complexity of Sinatra - he wasn't all bad nor was he all good. And what I appreciate is he takes this knowledge and doesn't let it taint the true genius of Sinatra - the musician. Say what you want about the way the guy lived his life, there's more than enough stories from Kaplan, but he was a genius with a lyric and a master recorder. He was a student of the music and had a real respect for the process. And what's so impressive, and maybe unknown to most, is how many times Sinatra kept coming back, his popularity may have waned here and there but he packed the concert halls till he stopped performing in 1995. His life was full of complicated relationship, some worth telling some worth forgetting, but the true love he had was for song. I think Kaplan captured that perfectly in both books. I honestly can't see myself reading another Sinatra biography again - 1600 pages - Kaplan has given me all the knowledge I need about the man! But I will continue to enjoy his music for many years to come.
May 13, 2020
A thoroughly interesting, well-researched, well-written account of an America icon, but also a story of a man loaded with contradictions. He was quite obviously one of the greatest American entertainers of any period of our history. What a voice, and as the author clearly shows, a superb interpreter of a song. He could turn a well-worn song into something fresh and new. One prime example is “New York, New York”. It’s impossible to think of Times Square at midnight on New Year’s Eve without his singing of this song. He helped raise untold amounts of money for charity. He gave some excellent performances in films such as The Man With the Golden Arm and The Manchurian Candidate. Any yet he had a horrible temper that led to some ugly fights and situations in which he humiliated people. He had, to put it mildly, a love em and leave em attitude towards women, with the exception of Ava Gardner, and even then they alternately loved and hated each other. He refused to keep Mafia figures out his life. Too often, his life revolved around his wants and needs. The author does a very good job of telling Frank Sinatra’s life in such a way that I ended up feeling both admiration of his talents and good points and sadness because of his raucous personal life.
January 7, 2018
I'm not sure what to think. This is certainly different from any other book I've read on Sinatra, yet it is probably the most honest portrayal of the man. I've always admired the beauty of Frank's voice and secretly had a girlish crush on him as well, but this book definitely opened my eyes to the man behind that gorgeous face.
What I take away from this book is that Frank was insecure and emotionally distant, incapable of having an intimate and lasting relationship with anyone on any level. I don't think he knew how to do that. For all his bravado, drinking and foul mouth rampages, he was really an insecure little man taking the lead with his bravado before anyone could discover the truth. Sadly, in the process, he became very unlikeable despite all the good things he did in life to make up for his bad behavior.
No one is perfect, least of all Frank Sinatra, but I still enjoy him anyway. The man was one of a kind and I don't believe we'll ever see another entertainer like him in our lifetime.
What I take away from this book is that Frank was insecure and emotionally distant, incapable of having an intimate and lasting relationship with anyone on any level. I don't think he knew how to do that. For all his bravado, drinking and foul mouth rampages, he was really an insecure little man taking the lead with his bravado before anyone could discover the truth. Sadly, in the process, he became very unlikeable despite all the good things he did in life to make up for his bad behavior.
No one is perfect, least of all Frank Sinatra, but I still enjoy him anyway. The man was one of a kind and I don't believe we'll ever see another entertainer like him in our lifetime.
November 12, 2017
This is an absolutely amazing read with an insane amount of detail, which is why it took me more than two months to finish. I took notes as I was reading, pausing at the mentions of albums so that I could put the record on (if I had it) or purchase a copy off eBay (if I didn't have it). And every mention of a name, I pulled up their Wikipedia article for a quick glimpse.
James Kaplan is an outstanding writer, and the depth of his research for this book --and The Voice -- is nothing short of impressive. It is easy to see that Kaplan is a huge fan of Sinatra's, but at the same time he did not hesitate to detail the numerous flaws of Frank. This is not an easy read for a causal fan, but I highly recommend it nonetheless.
James Kaplan is an outstanding writer, and the depth of his research for this book --and The Voice -- is nothing short of impressive. It is easy to see that Kaplan is a huge fan of Sinatra's, but at the same time he did not hesitate to detail the numerous flaws of Frank. This is not an easy read for a causal fan, but I highly recommend it nonetheless.
February 19, 2018
Meticulous and absolutely fascinating until Kaplan reaches Sinatra's short-lived 1971 "retirement." Then he shifts into hyper speed and blows through the last 25 years of the singer's life in a single chapter. We read nothing about Sinatra's last starring film role, his stint as the producer of Ronald Reagan's first inaugural celebration, or his lawsuit to block Kitty Kelley's extremely negative 1986 biography. Other late career events, like the abortive "Together Again" tour, are covered in the most cursory fashion. I don't know if Kaplan was facing an ironclad deadline or just got tired of his subject but his stumble caused me to knock a star off what had been an absolute five star book up to that point. Still recommended but with that caveat.
July 27, 2015
The story of “Ol’ Blue Eyes” continues with Sinatra: The Chairman, picking up the day after Frank claimed his Academy Award in 1954 and had reestablished himself as the top recording artist in music. Frank’s life post-Oscar was incredibly dense: in between recording albums and singles, he often shot four or five movies a year; did TV show and nightclub appearances; started his own label, Reprise; and juggled his considerable commercial ventures (movie production, the restaurant business, even prizefighter management) alongside an increasingly complicated personal life.
- Judy J., Doubleday Marketing Department
- Judy J., Doubleday Marketing Department
November 4, 2024
When I finished Sinatra: The Chairman, I took a few moments to decompress from all I had read about Frank Sinatra over the past month and a half. In September, I read part one of James Kaplan’s in-depth books about Sinatra – Frank: The Voice – and planned to read another book between volumes.
But I couldn’t do it. I had to know what happened next to Sinatra after his Oscars win for From Here to Eternity. My curiosity overwhelmed me, and I found myself back in the world of Sinatra, his music, movies, and many marriages.
The beauty of both books is how author James Kaplan presents a complete picture of Frank Sinatra. Kaplan explains his views on his subject in the Acknowledgments section of the first book: “My affection for him may have wavered – he had a genius, too, for making himself dislikable – but the one note I could never find within myself was condescension, even the contempt, on which so many other writers based their narratives” (720).
Frank Sinatra was a flawed human being, and Kaplan delivers the whole package to the reader and allows us to thoroughly analyze the man whose music has lived on for decades after his passing. Even when Frank was at his worst - there were a few moments where I was, like, “Gee, Frank. Take it down a notch.” – I had to see what happened next.
Would he find redemption? Would he find true happiness? Would he reach that elusive thing in his life that money and fame couldn’t help him achieve? As Kaplan writes: “If he continued to hold my affection despite his considerable, even spectacular, flaws, that was all well and good. It would sustain me. It did sustain me” (720).
It sustained me as well through both books.
Reading about the many historical events Sinatra was either a part of or witnessed, how technology in the music business changed, how the Hollywood studio system changed, and how Las Vegas evolved during Frank’s tenure makes him more than just an entertainer but a historical figure in his own right.
I also loved reading about the origins of the songs in Sinatra’s vast catalog. Learning about where the Married…with Children theme song, “Love and Marriage,” came from was quite interesting, along with dozens of other songs with intriguing backstories.
There were many times I would put the book down and seek out the songs mentioned. Often, it was a great listen (“Ring-A-Ding-Ding”), and other times, not so much (“Mama Will Bark”). I recommend doing this as you read, as it will create an interactive experience and immerse you into the musical world of Frank Sinatra over the decades. You may even find a Sinatra song or two you've never heard before.
Frank: The Voice and Sinatra: The Chairman by James Kaplan are both books I highly recommend. I’m glad I picked up both together at the bookstore; I would’ve kicked myself if I hadn’t.
But I couldn’t do it. I had to know what happened next to Sinatra after his Oscars win for From Here to Eternity. My curiosity overwhelmed me, and I found myself back in the world of Sinatra, his music, movies, and many marriages.
The beauty of both books is how author James Kaplan presents a complete picture of Frank Sinatra. Kaplan explains his views on his subject in the Acknowledgments section of the first book: “My affection for him may have wavered – he had a genius, too, for making himself dislikable – but the one note I could never find within myself was condescension, even the contempt, on which so many other writers based their narratives” (720).
Frank Sinatra was a flawed human being, and Kaplan delivers the whole package to the reader and allows us to thoroughly analyze the man whose music has lived on for decades after his passing. Even when Frank was at his worst - there were a few moments where I was, like, “Gee, Frank. Take it down a notch.” – I had to see what happened next.
Would he find redemption? Would he find true happiness? Would he reach that elusive thing in his life that money and fame couldn’t help him achieve? As Kaplan writes: “If he continued to hold my affection despite his considerable, even spectacular, flaws, that was all well and good. It would sustain me. It did sustain me” (720).
It sustained me as well through both books.
Reading about the many historical events Sinatra was either a part of or witnessed, how technology in the music business changed, how the Hollywood studio system changed, and how Las Vegas evolved during Frank’s tenure makes him more than just an entertainer but a historical figure in his own right.
I also loved reading about the origins of the songs in Sinatra’s vast catalog. Learning about where the Married…with Children theme song, “Love and Marriage,” came from was quite interesting, along with dozens of other songs with intriguing backstories.
There were many times I would put the book down and seek out the songs mentioned. Often, it was a great listen (“Ring-A-Ding-Ding”), and other times, not so much (“Mama Will Bark”). I recommend doing this as you read, as it will create an interactive experience and immerse you into the musical world of Frank Sinatra over the decades. You may even find a Sinatra song or two you've never heard before.
Frank: The Voice and Sinatra: The Chairman by James Kaplan are both books I highly recommend. I’m glad I picked up both together at the bookstore; I would’ve kicked myself if I hadn’t.
August 25, 2024
Somehow this was even worse than the first one. In all regards. It had all the same problems as the first book. Dense. Hard to follow. Focusing too much on the wrong stuff. But also it was chaotic and unbalanced.
This one had more ups and downs of being interesting than the first one. But the downs were way down and the ups just served to make the downs feel worse.
I can’t tell you how much of my time was spent lugging around these two very heavy books only to be able to get through a few pages at a time due to how hard to read, follow and care for it is.
It also stops before the last 20ish years of his life. Those years were fit entirely into a 40 page “Coda.” In a book series where one day in the earlier parts of his life could merit 6 pages. The argument was well made for how much less Frank did in those years and why it could be shorter and lumped together. But after the exhaustive detail oriented complexity of the rest, it somehow made the end of a book (that I literally could not wait to get to the end of) feel anticlimactic and unfinished. Not to mention a little rude to its subject.
The absolute worst thing though is the binding. In my opinion the only thing done truly right is the name of these two books. Book one is call Frank. Book two, Sinatra. Well done. Top marks. The binding of the first paperback is white with big black block letters filling the whole (not insignificantly thick) spine with the word Frank. As though it is waiting to be shelved next to its counterpart. (A little trophy I was hoping for after I made myself read all this nonsense).
The second book though? Published taller and slimmer, despite I believe being longer, in blue with skinny black cursive-ish letters that take up about a third of the (very regular sized) spine with the word Sinatra. You can almost miss it. Honestly it’s the most annoying part of what is the least enjoyable book I have ever read.
This one had more ups and downs of being interesting than the first one. But the downs were way down and the ups just served to make the downs feel worse.
I can’t tell you how much of my time was spent lugging around these two very heavy books only to be able to get through a few pages at a time due to how hard to read, follow and care for it is.
It also stops before the last 20ish years of his life. Those years were fit entirely into a 40 page “Coda.” In a book series where one day in the earlier parts of his life could merit 6 pages. The argument was well made for how much less Frank did in those years and why it could be shorter and lumped together. But after the exhaustive detail oriented complexity of the rest, it somehow made the end of a book (that I literally could not wait to get to the end of) feel anticlimactic and unfinished. Not to mention a little rude to its subject.
The absolute worst thing though is the binding. In my opinion the only thing done truly right is the name of these two books. Book one is call Frank. Book two, Sinatra. Well done. Top marks. The binding of the first paperback is white with big black block letters filling the whole (not insignificantly thick) spine with the word Frank. As though it is waiting to be shelved next to its counterpart. (A little trophy I was hoping for after I made myself read all this nonsense).
The second book though? Published taller and slimmer, despite I believe being longer, in blue with skinny black cursive-ish letters that take up about a third of the (very regular sized) spine with the word Sinatra. You can almost miss it. Honestly it’s the most annoying part of what is the least enjoyable book I have ever read.
October 4, 2022
Great second half of a biography on Frank Sinatra. Begins with Sinatra and Ava Gardner and moves to the his true end. The Rat Pack sticks together through thick and thin. Sammy Davis Jr said at one point that Frank could be supportive and caring like he was when he has his accident and lost his eye, but also unexpectedly cruel and hurtful. Sinatra behaved that way in several relationships. The book spends a lot of time on the Frank and Mia Farrow marriage which was volatile and a total mismatch. Mia apparently cut her hair short on a day when Frank was attending a party for his daughter Nancy and Mia wasn’t invited so Nancy’s mother wouldn’t get upset. Mia knew it would upset Frank and he was worried that people would accuse him of being gay. Indeed, Ava made a comment Frank of dating boys with cunts. Lots of good information in the book but one with heart and understanding.
May 18, 2022
I’m having a hard time trying to figure out just what sort of recommendation to give this book. I hate to say that one would have to be a Sinatra fan to read it, as that would exclude too many people who would miss out on an absolutely enthralling story. The only thing I can compare Kaplan’s amazing two-volume set (Frank: The Voice covers Frank from birth to From Here to Eternity) is the two volume set Peter Guralnick did on Elvis Presley. It depends on how much you want to learn about the career of a man who’s been called the greatest singer of the 20th century, an artist as creative as he was famous and someone who had an indelible effect on our popular culture. It depends on whether you want to crawl into the skin of a man who really isn’t playing with all his marbles. He’s a man who can be cruel and petty. He’s a man who can be involved in an incident where a restaurant patron is beaten with a heavy 1960s telephone so badly that it came close to killing him, for the sin of politely asking if Sinatra and his friends could keep their voices down at a restaurant. If you do decide to take that dive, you’ll be rewarded with a journey through the life of the most successful American entertainer of the 1960s. The Boomers might have pushed The Beatles into the #1 spot, but their parents made sure The Chairman of the Board was #2.
What makes this book so immersive is that Kaplan covers Sinatra’s life almost month-by-month, and what a whirlwind those months were. At least a hundred recording sessions, including some of the greatest albums ever made. An astounding 39 movies, not quite as many awful ones as Elvis did, but it’s close. Then again, Elvis never made an all-time classic like The Manchurian Candidate . Sinatra worked like he was either a man possessed or a man running from the demons trying to possess him.
One of those demons was his second wife, actress Ava Gardner. Their relationship played out like a Grand Guignal soap opera as the two fucked and fought, drank and screamed and, more than anything, loved each other for the rest of their lives. Kaplan tracks these moments and many others through the almost unimaginable research he’s done on this project, through ancient gossip columns and celebrity tabloids as well as many memoirs and biographies written by and about the people involved. Kaplan knows how to present the facts and write them so they sound interesting. He brings a novelist’s touch to his tale without having to embellish the truth. He also focuses on the music Sinatra was recording and, boy, was he recording some music! Albums were still relatively new in the mid-’50s and no one was using them like Sinatra was on his classic Capitol recordings. He would choose the songs to paint a certain mood. Sometimes the mood was upbeat, like my personal favorite, Songs for Swingin' Lovers! . Sometimes the mood was slow and lovelorn like the stunning Sings for Only the Lonely . Kaplan never loses his focus on Sinatra the artist and I would have to say that his critical eye is on point. If there’s something Kaplan suggests you should listen to, it’s definitely worth your while. If there’s music that can best be avoided, you won’t miss much.
This book may be long but it is never boring. The most fault I can find is that there are times Kaplan strays a bit off-track with over-involved discourses on the organized crime members in Sinatra’s orbit or Frank’s pussy-hound buddy John Kennedy’s history. I’ve read a few other Sinatra bios and this one is by far the best. It’s an intensely-captivating look at one of the most important people of mid-20th-century America.
Completely Pointless Facts That You Can Skip Department
1. Sinatra is the only artist to have a Billboard Top 40 hit in the ‘40s, ‘50s, ‘60s and ‘70s. That’s what Casey Kasem told me when “New York, New York” hit the Top 40 in 1979. At the time he was the only artist to do a four-decade stretch. I think The Beatles have tied him since then, but Frank was first.
2. Sinatra was the third biggest-selling album artist of the 1960s. The Beatles were first, Elvis with his glut of movie soundtracks was second and Sinatra was third. That always kind of freaks me out! It wasn’t any of the other groovy rock bands that the kids were listening to. Not The Stones, not Zeppelin, but good ol’ ring-a-ding-ding Frank Sinatra!
What makes this book so immersive is that Kaplan covers Sinatra’s life almost month-by-month, and what a whirlwind those months were. At least a hundred recording sessions, including some of the greatest albums ever made. An astounding 39 movies, not quite as many awful ones as Elvis did, but it’s close. Then again, Elvis never made an all-time classic like The Manchurian Candidate . Sinatra worked like he was either a man possessed or a man running from the demons trying to possess him.
One of those demons was his second wife, actress Ava Gardner. Their relationship played out like a Grand Guignal soap opera as the two fucked and fought, drank and screamed and, more than anything, loved each other for the rest of their lives. Kaplan tracks these moments and many others through the almost unimaginable research he’s done on this project, through ancient gossip columns and celebrity tabloids as well as many memoirs and biographies written by and about the people involved. Kaplan knows how to present the facts and write them so they sound interesting. He brings a novelist’s touch to his tale without having to embellish the truth. He also focuses on the music Sinatra was recording and, boy, was he recording some music! Albums were still relatively new in the mid-’50s and no one was using them like Sinatra was on his classic Capitol recordings. He would choose the songs to paint a certain mood. Sometimes the mood was upbeat, like my personal favorite, Songs for Swingin' Lovers! . Sometimes the mood was slow and lovelorn like the stunning Sings for Only the Lonely . Kaplan never loses his focus on Sinatra the artist and I would have to say that his critical eye is on point. If there’s something Kaplan suggests you should listen to, it’s definitely worth your while. If there’s music that can best be avoided, you won’t miss much.
This book may be long but it is never boring. The most fault I can find is that there are times Kaplan strays a bit off-track with over-involved discourses on the organized crime members in Sinatra’s orbit or Frank’s pussy-hound buddy John Kennedy’s history. I’ve read a few other Sinatra bios and this one is by far the best. It’s an intensely-captivating look at one of the most important people of mid-20th-century America.
Completely Pointless Facts That You Can Skip Department
1. Sinatra is the only artist to have a Billboard Top 40 hit in the ‘40s, ‘50s, ‘60s and ‘70s. That’s what Casey Kasem told me when “New York, New York” hit the Top 40 in 1979. At the time he was the only artist to do a four-decade stretch. I think The Beatles have tied him since then, but Frank was first.
2. Sinatra was the third biggest-selling album artist of the 1960s. The Beatles were first, Elvis with his glut of movie soundtracks was second and Sinatra was third. That always kind of freaks me out! It wasn’t any of the other groovy rock bands that the kids were listening to. Not The Stones, not Zeppelin, but good ol’ ring-a-ding-ding Frank Sinatra!
September 30, 2016
Frank Sinatra was a singer, an actor, a legend. He was a generous humanitarian, a kind friend and a loving husband and father.
He was also a grown-up street thug who wanted to play with the big Mafia boys, a man with his eye on the prize at every given moment and often a cruel companion to his friends and lovers in moments of embarrassment, stress or humiliation.
With all those contradictions to talk about, it's no wonder writer, reviewer and bestselling author James Kaplan's newest biography takes nearly 1,000 pages to chronicle just 17 years of Sinatra's life, between 1954 and 1971. What's particularly unexpected is how compelling the story is and how every one of those pages is eminently readable.
Kaplan's extensive research, eye for detail and skill at turning a phrase make Sinatra: The Chairman a worthy followup to his 2010 New York Times bestseller Sinatra: The Voice.
He picks up where the first book left off, as Sinatra begins his comeback in March 1954 by accepting a Best Supporting Actor Oscar for his role in From Here to Eternity. This volume's filled to the brim with tidbits about Sinatra and other stars of the era, such as Bogie and Bacall, Bing Crosby, Dean Martin and Sammy Davis Jr.
After winning the Oscar, Sinatra kept busy making movies, recording albums, performing in Las Vegas and making television appearances. The story shifts from Miami to Las Vegas to New York to Hollywood, back and forth, again and again, following a man who is unable to be alone or spend time with his own thoughts, and always travels with an entourage.
Kaplan delivers lines with a panache befitting Sinatra himself. "Dooby dooby doo was the new ring-a-ding-ding," he says of the success of Strangers in the Night, managing not to sound slick or flippant. He has a real knack for looking at several points of view and offering plausible explanations as to what motivated Sinatra's actions without apologizing for the behaviour, good or bad.
Sinatra's dramatic personal life is also recounted in detail. He would divorce actress Ava Gardner in 1957 and get into, and then out of, an ill-fated marriage to Mia Farrow in the late 1960s before marrying Barbara Marx in 1976. But no matter his marital status, he kept busy with many women at once, including starlets Peggy Connelly and Kim Novak, as well as the widowed Lauren Bacall among oh-so-many others.
Sinatra's blazing temper and capacity for icy coolness to those who displeased him made being around him unpredictable. The crooner known for inhabiting the emotion of almost every song he sang seemed incapable of doing the same in his daily life, as Kaplan discovers through interviews with surviving family and friends, as well as media coverage of the day and other biographies.
Kaplan's reviewing background makes his sections on Sinatra's career particularly interesting, providing almost mini-reviews of the scores of albums and movies Sinatra worked on during this period. He's not afraid to criticize a poor performance or praise a good one, and makes the history relevant by, for example, describing a character in a Sinatra movie as a proto-Don Draper, creating a link between 60 years ago and today.
The late 1950s was also when the infamous Rat Pack concept was formed. The name originated at a party at the home of Humphrey Bogart, but after Bogie's death, the name began to be applied to the entourage surrounding Sinatra.
Kaplan notes the legend of the Rat Pack greatly outweighed the real thing:
"The Rat Pack was an idea, even more than it was a reality. And though Frank, Dean (Martin) and Sammy (Davis Jr.) were three real men, their respective myths tend, to this day, to jostle reality aside. Throw in Joey Bishop and Peter Lawford as window dressing, or ballast, and you've got a sharkskin-suited, skinny-tied, chain-smoking, chain-drinking Dionysian parade float. Watch it trundle down Main Street, cheer as it goes by. We won't see its likes again. Even if it wasn't quite there in the first place."
Most of the legend relates to a time when the crew was in Vegas filming Ocean's Eleven, when they all took to the stage for two shows a night of never-before-seen debauchery and off-colour jokes at the Sands.
Kaplan also highlights Sinatra's connection to both John F. Kennedy and the Mafia, in particular Chicago mob boss Sam Giancana, as well as later connections to U.S. presidents Johnson, Nixon and Reagan.
In Sinatra: The Chairman, Kaplan's grasp of the fears, emotions and inner turmoil of a legend is masterful, and leaves the reader hanging on every word.
He was also a grown-up street thug who wanted to play with the big Mafia boys, a man with his eye on the prize at every given moment and often a cruel companion to his friends and lovers in moments of embarrassment, stress or humiliation.
With all those contradictions to talk about, it's no wonder writer, reviewer and bestselling author James Kaplan's newest biography takes nearly 1,000 pages to chronicle just 17 years of Sinatra's life, between 1954 and 1971. What's particularly unexpected is how compelling the story is and how every one of those pages is eminently readable.
Kaplan's extensive research, eye for detail and skill at turning a phrase make Sinatra: The Chairman a worthy followup to his 2010 New York Times bestseller Sinatra: The Voice.
He picks up where the first book left off, as Sinatra begins his comeback in March 1954 by accepting a Best Supporting Actor Oscar for his role in From Here to Eternity. This volume's filled to the brim with tidbits about Sinatra and other stars of the era, such as Bogie and Bacall, Bing Crosby, Dean Martin and Sammy Davis Jr.
After winning the Oscar, Sinatra kept busy making movies, recording albums, performing in Las Vegas and making television appearances. The story shifts from Miami to Las Vegas to New York to Hollywood, back and forth, again and again, following a man who is unable to be alone or spend time with his own thoughts, and always travels with an entourage.
Kaplan delivers lines with a panache befitting Sinatra himself. "Dooby dooby doo was the new ring-a-ding-ding," he says of the success of Strangers in the Night, managing not to sound slick or flippant. He has a real knack for looking at several points of view and offering plausible explanations as to what motivated Sinatra's actions without apologizing for the behaviour, good or bad.
Sinatra's dramatic personal life is also recounted in detail. He would divorce actress Ava Gardner in 1957 and get into, and then out of, an ill-fated marriage to Mia Farrow in the late 1960s before marrying Barbara Marx in 1976. But no matter his marital status, he kept busy with many women at once, including starlets Peggy Connelly and Kim Novak, as well as the widowed Lauren Bacall among oh-so-many others.
Sinatra's blazing temper and capacity for icy coolness to those who displeased him made being around him unpredictable. The crooner known for inhabiting the emotion of almost every song he sang seemed incapable of doing the same in his daily life, as Kaplan discovers through interviews with surviving family and friends, as well as media coverage of the day and other biographies.
Kaplan's reviewing background makes his sections on Sinatra's career particularly interesting, providing almost mini-reviews of the scores of albums and movies Sinatra worked on during this period. He's not afraid to criticize a poor performance or praise a good one, and makes the history relevant by, for example, describing a character in a Sinatra movie as a proto-Don Draper, creating a link between 60 years ago and today.
The late 1950s was also when the infamous Rat Pack concept was formed. The name originated at a party at the home of Humphrey Bogart, but after Bogie's death, the name began to be applied to the entourage surrounding Sinatra.
Kaplan notes the legend of the Rat Pack greatly outweighed the real thing:
"The Rat Pack was an idea, even more than it was a reality. And though Frank, Dean (Martin) and Sammy (Davis Jr.) were three real men, their respective myths tend, to this day, to jostle reality aside. Throw in Joey Bishop and Peter Lawford as window dressing, or ballast, and you've got a sharkskin-suited, skinny-tied, chain-smoking, chain-drinking Dionysian parade float. Watch it trundle down Main Street, cheer as it goes by. We won't see its likes again. Even if it wasn't quite there in the first place."
Most of the legend relates to a time when the crew was in Vegas filming Ocean's Eleven, when they all took to the stage for two shows a night of never-before-seen debauchery and off-colour jokes at the Sands.
Kaplan also highlights Sinatra's connection to both John F. Kennedy and the Mafia, in particular Chicago mob boss Sam Giancana, as well as later connections to U.S. presidents Johnson, Nixon and Reagan.
In Sinatra: The Chairman, Kaplan's grasp of the fears, emotions and inner turmoil of a legend is masterful, and leaves the reader hanging on every word.
January 25, 2017
Would you like to spend a month reading about the women Sinatra slept with and the men he feuded with?
ByArmen Pandolaon January 24, 2017
If you spend over 900 pages telling me the story of 16 years somebody's life, the somebody had better be FDR during his presidency or Alexander The Great when he conquered the known world. As a Sinatra fan (I have ALL of Sinatra's recording with Columbia, Capitol and Reprise) I welcomed the few insights and stories about the making of the best popular music of our time. Kaplan has listened to the outtakes of the recording sessions, read Sinatra: The Song Is You and spoken to some of the musicians, but he has a tin ear. For example, incredibly, he thinks that the best Sinatra album of the 60's was Academy Award Winners. Not even close. He falls in with the general perception that Sinatra was loosing it in the late 60's with his low-selling albums, Watertown and A Man Alone. In fact, they are two of the best albums Sinatra recorded. He calls JImmy van Huesen a pimp! He has no time for many of the most beautiful songs in Sinatra's catalog - like the incredible Our Town.
90% of the book is about Sinatra's sex and scandal life. Pages upon chapters tells us about all the women he bedded, all the men he fought with and all the booze he drank. Most of it is pure speculation or worse - somebody has a story to tell. For example, it seems that Sinatra was attracted to beautiful widows, Lauren Bacall and Jackie Kennedy among them. One very rich widow who was 'part of society' was wooed by Sinatra and she claimed that he asked her to marry him. According to her, she told him, "Frank, I could never marry you - you're a hoodlum." Really?
Kaplan doesn't think much of the Rat Pack. Viewing the antics of its members with 20/20 hindsight, he thinks it was all childish, racist, misogynist crap. He doesn't think much of Oceans 11 and actually states that the new ones are much better. He has no time for Robin and the Seven Hoods (one of the best movie scores ever written).
He likes Sinatra's version of Mrs. Robinson. He doesn't like most other songs on the My Way album.
Well, everybody has their own opinion but if you are going to write a James Michner sized book about an entertainer, you had better figure out why before you write it. After over 900 pages, I don't know why. I learned nothing new. Yeah, I probably wouldn't have liked to hang around with Sinatra for more than one night and only then if I wanted to punish my liver. Yeah, he culd be a creep. Yeah, he could also be very generous. Yeah, he was a real enigma. Yeah, he was one of the most ambitious people to sing a song,
Ultimately it is the music that will define what we think of Sinatra. Thank god
ByArmen Pandolaon January 24, 2017
If you spend over 900 pages telling me the story of 16 years somebody's life, the somebody had better be FDR during his presidency or Alexander The Great when he conquered the known world. As a Sinatra fan (I have ALL of Sinatra's recording with Columbia, Capitol and Reprise) I welcomed the few insights and stories about the making of the best popular music of our time. Kaplan has listened to the outtakes of the recording sessions, read Sinatra: The Song Is You and spoken to some of the musicians, but he has a tin ear. For example, incredibly, he thinks that the best Sinatra album of the 60's was Academy Award Winners. Not even close. He falls in with the general perception that Sinatra was loosing it in the late 60's with his low-selling albums, Watertown and A Man Alone. In fact, they are two of the best albums Sinatra recorded. He calls JImmy van Huesen a pimp! He has no time for many of the most beautiful songs in Sinatra's catalog - like the incredible Our Town.
90% of the book is about Sinatra's sex and scandal life. Pages upon chapters tells us about all the women he bedded, all the men he fought with and all the booze he drank. Most of it is pure speculation or worse - somebody has a story to tell. For example, it seems that Sinatra was attracted to beautiful widows, Lauren Bacall and Jackie Kennedy among them. One very rich widow who was 'part of society' was wooed by Sinatra and she claimed that he asked her to marry him. According to her, she told him, "Frank, I could never marry you - you're a hoodlum." Really?
Kaplan doesn't think much of the Rat Pack. Viewing the antics of its members with 20/20 hindsight, he thinks it was all childish, racist, misogynist crap. He doesn't think much of Oceans 11 and actually states that the new ones are much better. He has no time for Robin and the Seven Hoods (one of the best movie scores ever written).
He likes Sinatra's version of Mrs. Robinson. He doesn't like most other songs on the My Way album.
Well, everybody has their own opinion but if you are going to write a James Michner sized book about an entertainer, you had better figure out why before you write it. After over 900 pages, I don't know why. I learned nothing new. Yeah, I probably wouldn't have liked to hang around with Sinatra for more than one night and only then if I wanted to punish my liver. Yeah, he culd be a creep. Yeah, he could also be very generous. Yeah, he was a real enigma. Yeah, he was one of the most ambitious people to sing a song,
Ultimately it is the music that will define what we think of Sinatra. Thank god
January 31, 2018
In 2010, James Kaplan wrote an eight-hundred page volume about a poor kid from Hoboken, who made it good as a singer, seemed to flame out in the early '40s, and came back with a bang on the silver screen. The kid who was once floored by punches and got back up is now gone, replace by an increasingly wealthy artist-producer who can seemingly get away with anything, and who will remain an icon for the rest of his life, long after the Beatles and all that follow take over the pop charts. If The Voice followed 'Frankie' from the gutter to the top, The Chairman is a chronicle of Sinatra's use and abuse of his cultural and financial power as the king of entertainment -- for even as his behavior became worse under the influence of constant adulation, his growing wealth and legendary status allowed him to get away with the same behavior that nearly ended young Frankie's career. This is not a biography for the reader who merely wants to delight in how cool Sinatra was -- there are other books for that -- because the Sinatra here is frequently drunk, ugly, and...well, very un-cool. But Kaplan has produced in these two books a definitive biography, one that dwells at length on Sinatra's artistry as well as his relationships with others, and the good and bad flow together. Although its sheer volume nearly exhausted my considerable interest, at the end I had to count it worth it.
Artistically, Sinatra seems to have peaked in the 1950s: after that, both the changing tastes of the music-buying populace, and Sinatra's growing age and iconic status cut his edge. He never ceased to take music seriously, and after initially dismissing Elvis and the Beatles as so much noise, he would listen to them attentively in hopes of figuring out why kids liked them so much, but movies were a different story. Sinatra's comeback was based on his outstanding performance in From Here to Eternity, and while there would be a few more stellar roles to come, after Sinatra gained the wealth and stature to start trying to make his own movies, he would produce films that sold through star power alone. Sinatra couldn't lose himself in acting the way he did while singing, and as a result a lot of his later movies have characters who are just Frank Sinatra with a different name; there's no suspension of disbelief. On the set, Sinatra was increasingly disinclined to heed direction, and produced a lot of films that were panned by critics and lukewarmly attended, but let him pal around with his buddies. He remained committed to music, however, and the main reason I kept plugging along was for Kaplan's evaluations of different songs and records; aside from his late Capitol years, when Sinatra was utterly resentful of their refusal to let him go to develop his own label, Sinatra was a consummate professional about not just singing, but musical performance. Sinatra didn't just stand in front of a microphone and sing; he played the mic like an instrument, using it to hide his deficiencies and embellish his strengths. He also experimented with different musical styles, though he was at his happiest giving performances like those of his youth: the singer and a big band behind him, thrilling now grey-haired bobby soxers.
A major part of The Chairman is Sinatra's relationships with others, as Kaplan covers his string of wives, his panel of good and lose friends, and his allies and enemies. Sinatra liked to have a good time, preferring to stay up all night drinking Jack Daniels with his friends, and he was rarely without female company whether or not he was married at the time. (Sinatra definitely got around, often seeing several women simultaneously, and apparently without an attempt to be secretive.) Sinatra's serial romances weren't just about having an interesting dinner companion for the evening; he was ever restless, always looking for someone who could fill a lonely void. His frequent heartache, particularly the long-burning torch for his second wife Ava, also informed his music, allowing him to sing songs about lost love like no one else. He was attracted to power and swagger; throughout his life he'd pal around with members of the Mafia, despite being hauled into court several times to be questioned about mob ties. Sinatra embodied that swagger himself, and without a powerful person to manage him, he wasn't far from acting out if someone angered him. (He once drove a golf cart through a casino window after they changed owners and stopped his line of credit.) The lure of power also brought him to DC, as he sought the friendship of JFK, and would later schmooze with Governor Ronald Reagan and President Nixon despite being a Democrat. Kennedy, whose own lechery was on par with Sinatra's, was the only person whose fame ever rivaled Sinatra's, but his wife and brother did their best to keep Sinatra away from Kennedy. Kaplan also covers the Rat Pack at length, Sinatra's clan of buddies who made films with him and who for a while took over Las Vegas with their shenanigans. While filming Ocean's Eleven, they began disrupting and then taking over each other's shows, to the point that it didn't matter who was booked: Sinatra, Martin, or Davis. They'd all wind up on stage together, drinking and carrying on. The jokes and act grew old after a while, but in the early sixties nothing like this had been seen before.
The Chairman covers Sinatra's life at length until the early seventies, when he entered into a "retirement" that was shorter than his marriage to the child-bride Mia Farrow. He came back in less than two years, and would continue to perform until the 1990s...but this last chapter of his life is a very small part of the book, and mostly chronicles his friends dying and Sinatra himself growing more tired, until his death in 1998. Kaplan also includes a touching epilogue about a visit to Sinatra's grave in Cathedral City, where the larger-than-life singer rests under a very ordinary marker that will probably be completely sun-bleached in another generation. The music, however, will persist. There many singers who are descended in chaos after imbibing too much fame and money, but what they produce overshadows it: that's definitely the case with Sinatra. He was a complex man who could give to charities lavishly, with complete anonymity, and then cause a public scandal -- but when I listen to something like "Summer Wind", all of the tabloid bits are blown away. The voice takes over, and I can only marvel at the story of this poor kid from the wrong side of the river who became an icon -- and one whose wealth was produced not through dishonest means, like politics and crime, but through the sheer joy he brought to people who bought his records. It's a heckuva story, and in Kaplan's version, a heckuva read.
Artistically, Sinatra seems to have peaked in the 1950s: after that, both the changing tastes of the music-buying populace, and Sinatra's growing age and iconic status cut his edge. He never ceased to take music seriously, and after initially dismissing Elvis and the Beatles as so much noise, he would listen to them attentively in hopes of figuring out why kids liked them so much, but movies were a different story. Sinatra's comeback was based on his outstanding performance in From Here to Eternity, and while there would be a few more stellar roles to come, after Sinatra gained the wealth and stature to start trying to make his own movies, he would produce films that sold through star power alone. Sinatra couldn't lose himself in acting the way he did while singing, and as a result a lot of his later movies have characters who are just Frank Sinatra with a different name; there's no suspension of disbelief. On the set, Sinatra was increasingly disinclined to heed direction, and produced a lot of films that were panned by critics and lukewarmly attended, but let him pal around with his buddies. He remained committed to music, however, and the main reason I kept plugging along was for Kaplan's evaluations of different songs and records; aside from his late Capitol years, when Sinatra was utterly resentful of their refusal to let him go to develop his own label, Sinatra was a consummate professional about not just singing, but musical performance. Sinatra didn't just stand in front of a microphone and sing; he played the mic like an instrument, using it to hide his deficiencies and embellish his strengths. He also experimented with different musical styles, though he was at his happiest giving performances like those of his youth: the singer and a big band behind him, thrilling now grey-haired bobby soxers.
A major part of The Chairman is Sinatra's relationships with others, as Kaplan covers his string of wives, his panel of good and lose friends, and his allies and enemies. Sinatra liked to have a good time, preferring to stay up all night drinking Jack Daniels with his friends, and he was rarely without female company whether or not he was married at the time. (Sinatra definitely got around, often seeing several women simultaneously, and apparently without an attempt to be secretive.) Sinatra's serial romances weren't just about having an interesting dinner companion for the evening; he was ever restless, always looking for someone who could fill a lonely void. His frequent heartache, particularly the long-burning torch for his second wife Ava, also informed his music, allowing him to sing songs about lost love like no one else. He was attracted to power and swagger; throughout his life he'd pal around with members of the Mafia, despite being hauled into court several times to be questioned about mob ties. Sinatra embodied that swagger himself, and without a powerful person to manage him, he wasn't far from acting out if someone angered him. (He once drove a golf cart through a casino window after they changed owners and stopped his line of credit.) The lure of power also brought him to DC, as he sought the friendship of JFK, and would later schmooze with Governor Ronald Reagan and President Nixon despite being a Democrat. Kennedy, whose own lechery was on par with Sinatra's, was the only person whose fame ever rivaled Sinatra's, but his wife and brother did their best to keep Sinatra away from Kennedy. Kaplan also covers the Rat Pack at length, Sinatra's clan of buddies who made films with him and who for a while took over Las Vegas with their shenanigans. While filming Ocean's Eleven, they began disrupting and then taking over each other's shows, to the point that it didn't matter who was booked: Sinatra, Martin, or Davis. They'd all wind up on stage together, drinking and carrying on. The jokes and act grew old after a while, but in the early sixties nothing like this had been seen before.
The Chairman covers Sinatra's life at length until the early seventies, when he entered into a "retirement" that was shorter than his marriage to the child-bride Mia Farrow. He came back in less than two years, and would continue to perform until the 1990s...but this last chapter of his life is a very small part of the book, and mostly chronicles his friends dying and Sinatra himself growing more tired, until his death in 1998. Kaplan also includes a touching epilogue about a visit to Sinatra's grave in Cathedral City, where the larger-than-life singer rests under a very ordinary marker that will probably be completely sun-bleached in another generation. The music, however, will persist. There many singers who are descended in chaos after imbibing too much fame and money, but what they produce overshadows it: that's definitely the case with Sinatra. He was a complex man who could give to charities lavishly, with complete anonymity, and then cause a public scandal -- but when I listen to something like "Summer Wind", all of the tabloid bits are blown away. The voice takes over, and I can only marvel at the story of this poor kid from the wrong side of the river who became an icon -- and one whose wealth was produced not through dishonest means, like politics and crime, but through the sheer joy he brought to people who bought his records. It's a heckuva story, and in Kaplan's version, a heckuva read.
December 22, 2021
The second and final part of this vaguely epic biography is much like the first: gossipy, psychologically enlightening and with a real feel for the records. If I don’t always agree with Kaplan’s takes (‘Cycles’ is one of my favourite Sinatra vocals, and ‘Watertown’ – whatever the pretensions of its admirers – is just a stunning album), they’re invariably thought-provoking, enlightening and sincere. Somehow he also manages to square the apparently irreconcilable elements of his subject: the sensitive artist and the cowardly, selfish bully.
But while the book is great on the man and his music it’s rather long-winded on both JFK and the mob. And though Kaplan displays his familiar tenacity when it comes to getting at the truth, as well as reining in his chattier first-person tendencies, The Chairman is also bittier than the earlier volume – especially as it progresses.
It’s perhaps most memorable – and funny – when digging into Frank’s own relationship with his later work. It’s fascinating to me that the singer compromised his artistic integrity because of a terror that the world was leaving him behind, and is now largely known – both positively and negatively – for the records he hated or thought beneath him (most notably ‘Strangers in the Night’, which he initially dismissed with the words, “I don’t want to sing this. It’s a piece of shit.”). While that isn’t a unique story, it’s rarely seen to this degree.
But while the book is great on the man and his music it’s rather long-winded on both JFK and the mob. And though Kaplan displays his familiar tenacity when it comes to getting at the truth, as well as reining in his chattier first-person tendencies, The Chairman is also bittier than the earlier volume – especially as it progresses.
It’s perhaps most memorable – and funny – when digging into Frank’s own relationship with his later work. It’s fascinating to me that the singer compromised his artistic integrity because of a terror that the world was leaving him behind, and is now largely known – both positively and negatively – for the records he hated or thought beneath him (most notably ‘Strangers in the Night’, which he initially dismissed with the words, “I don’t want to sing this. It’s a piece of shit.”). While that isn’t a unique story, it’s rarely seen to this degree.
July 28, 2016
This is the second volume in Kaplan's two-volume biography of Frank Sinatra. (my review here). The Chairman picks up where The Voice left off - with Sinatra's role as Maggio in From Here to Eternity; the role that resurrected his career and started him on the road, not just to stardom, but to legend. This is the Sinatra at the peak of his vocal powers, recording some 46 plus albums over the next 30 years. It's the Sinatra of My Kind of Town and My Way.
It's also the Sinatra of Vegas, the Rat Pack, mob connections and belligerence. It's the Sinatra of broads, babes, and booze. The Chairman of the Board, the Leader.
Like its predecessor, The Chairman is best when discussing the man and his relationship to his music. As interesting as the stories of his relationship to the Kennedys, his public brawls, and his marriage to Mia Farrow are, the real Sinatra comes alive in the recording studio. Kaplan (an obvious fan) has a way of making us see that this is a consummate professional, admired not only by his fans but by fellow musicians, arrangers, and conductors. I recommend readings these books with a good pair of earphones in order to follow the path of his music and truly understand what a powerful talent was Frank Sinatra.
It's also the Sinatra of Vegas, the Rat Pack, mob connections and belligerence. It's the Sinatra of broads, babes, and booze. The Chairman of the Board, the Leader.
Like its predecessor, The Chairman is best when discussing the man and his relationship to his music. As interesting as the stories of his relationship to the Kennedys, his public brawls, and his marriage to Mia Farrow are, the real Sinatra comes alive in the recording studio. Kaplan (an obvious fan) has a way of making us see that this is a consummate professional, admired not only by his fans but by fellow musicians, arrangers, and conductors. I recommend readings these books with a good pair of earphones in order to follow the path of his music and truly understand what a powerful talent was Frank Sinatra.
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