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Sinatra! The Song is You: A Singer s Art

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A musical biography documents Frank Sinatra's legacy through seven decades, including The Skinny Years in the 1930s and 1940s; The Hat Years of the 1950s, 1960s, and 1970s; and the Tux Years of the 1980s and 1990s. 25,000 first printing.

560 pages, Hardcover

First published August 30, 1995

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Will Friedwald

25 books14 followers

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Displaying 1 - 18 of 18 reviews
286 reviews7 followers
September 7, 2020
I've had this book on my bookshelf for years, and never read it through from cover to cover until now. I dipped into it countless times, usually while listening to a Sinatra album, so that I could read the story behind the recordings as I'm listening to them. And Friedwald helped me to notice things that I had missed.

I purchased my first Sinatra album in 1983, and have since become a rabid Sinatraphile. I have 8 books on the man, and 75 different recordings (albums and live concerts, in vinyl, cassette, and CD formats). This book was a real eye-opener.

As you would guess from the subtitle, the book focuses on Sinatra's art, on his recording sessions and his concerts. Friedwald has based his book on countless interviews, conversations, and writings by all kinds of people in the music business: musicians, singers, arrangers, producers, industry executives, and family members. The portrait that emerges is the incredible musicianship of the greatest interpreter of popular song in the 20th century.

Friedwald takes us through Sinatra's entire performing career of 60 (!) years, beginning with his singing on a local Jersey City radio station in 1935 to his last performance at his wife's annual charity event and golf outing in 1995, a little over three years before his death. He takes us through the early years of singing at local clubs, to signing on with Harry James' orchestra, and later Tommy Dorsey's orchestra, to his going out on his own (the first big band singer to do so, and arguably the most successful), through his years at Columbia, then Capitol, then his own Reprise recording company, through the concert years, and up to the execrable "Duets" recordings (as Friedwald notes, it was the one time in Sinatra's career that he sacrificed art for economics).

Throughout the book we are introduced to the dazzling variety of musicians, arrangers, and producers with whom Sinatra worked. To a man (or woman, such as Eleanor Slatkin, Sinatra's preferred cellist), they praised Sinatra's musicianship, professionalism, and talent. When Sinatra walked into the recording studio, all the musicians immediately went up a level or two, as drummer Irv Cottler said. Even though he could not read music, Sinatra understood it so well that he would at times conduct, and by all accounts was at least as good as any of his arrangers/conductors (with the exception of Axel Stordahl). As to his tastes, "Frank has the finest musical taste that I've ever run into," said arranger Gordon Jenkins. They all loved working with him because he understood and appreciated what they were doing, and would compliment them (he also had the habit of constantly naming and giving credit to musicians, arrangers, and songwriters during his concerts, no doubt endearing himself to all of them). But everyone knew that things would be done Frank's way, which meant he demanded--and expected--nothing but everyone's best effort. Occasionally, they would even do a song in one take, which is inconceivable today.

I thought I knew a lot about Sinatra, but I learned so much more through this book. Since I am not a musician myself, a lot of the technical aspects of which Friedwald writes are beyond me; but I'm sure that they would be immediately understandable and helpful to a musician.

There is so much more in the book that I haven't even touched on in this review. All I can say is, if you are at all interested in Francis Albert Sinatra, and particularly if you are a musician or singer, find and read this book. And I strongly suggest that you have a LOT of Sinatra recordings close at hand, so that you can listen to them after you read about them in the book.
Profile Image for Chuck Zak.
49 reviews3 followers
June 29, 2012
Time to trot out a Yogi Berra quote "If you like this sorta thing, this is the sorta thing you'll like," or words to that effect. Basically, if you're more interested in Sinatra's drummers and arrangers than in his lovers and Mob friends, this is a book you will enjoy.

The fun is all in the facts. Each era of Sinatra's career is covered in detail, with plenty of attention to his arrangers and the musicians he used, and the book reads like one looooong record review. And though the fawning tone was a bit much at first, it kinda settled into a groove once Friedwald got into details and had specifics to hang all those words of praise upon.

I for one enjoy reading record reviews, especially when they are either really positive or really negative, so this book had the same effect. And Friedwald does a good job of explaining why I should be as enamored of Frank as he is, which makes me want to listen to everything he is discussing, which is exactly why I enjoy reading about music.

And the author isn't afraid to get tough with Sinatra over his less successful efforts, which multiply once you get past the glory years of the Capitol Era and early Reprise stuff. Unfortunately, as Sinatra's quality gets more erratic, Friedwald gets more cranky toward every other artist who isn't Sinatra - and he repeatedly airs his total disdain for any contemporary pop, sounding way more like an out-of-touch coot than he is (the dude was only in his mid-30s when he wrote this). The digs at Neil Diamond, Barry Manilow and John Denver are unintentionally funny and only serve to make the author seem more lost – and whatever you do, don’t ask him about Bono!

His writing too is peppered with a lot of weak attempts at hep-cat humor which are distracting and not very funny. Just tell the story.

But it is a great story, and the mammoth Sinatra catalog is breathtaking in its sheer size and in the amount of incredible music contained within. Just reading about all the albums and songs and live dates and airchecks was exciting, if only to promise a depth of experience beyond those classic hits and classic albums for the curious Sinatra fan.

For modern musicians, it’s kinda sobering to read about the technical and interpretive agility of the players in those days, all amazing musicians and sightreaders, able to turn this demanding music into effortlessly elegant and fun music while under the merciless pressure of getting those tracks right, all the way through, all at once, no dropped notes and no overdubs. That’s a level of musicianship that is pretty much non-existent in pop today – which is fine, because the trade off is that we get so many different creators in the game who aren’t constrained by those rules. But still, it is very impressive and a great testament to a bygone era. But I digress…

So, a good read, but only for a small audience. Everyone else, just go queue up one of 10 million Sinatra versions of “Night And Day.”
Profile Image for Bill.
16 reviews5 followers
July 16, 2008
Sinatra is one of the most important musicians America produced in the 20th Century, and it is much more interesting to know that the valve trombonist on "Night and Day" was from the Ellington band than it is to read about a bodyguard smashing a photographer's camera. "I'm A Fool To Want You" is much more interesting than the stories about Sinatra and Ava Gardner throwing ashtrays at each other.

Freidwald tells us about song structure, and recording sessions, and the musician's strikes and recording bans, and the aesthetic decisions and stylistic choices Sinatra and his various arrangers made; contrasts versions of different songs (there's a great discussion of how "Night And Day"'s structure works). If I have a criticism, it would be that at times Freidwald is a little too inside baseball. I've been listening to this music for years, including Sunday mornings spent with Jonathan Schwartz's scholarly discussions, but some of this (discussions of available in England only airchecks, e.g.) was on beyond zebra as far as I'm concerned. A pleasure, even if the writing is sometimes a little too cute for its own good.
Profile Image for Lynn.
3,386 reviews71 followers
September 29, 2021
More about the musical history of Sinatra rather than his life which I understood before reading it. But a lot is over my head because my lack of knowledge. But it a worthwhile read, I think an audiophile and someone more knowledgeable about Sinatra might get more out of it.
Profile Image for Spencer Rich.
196 reviews26 followers
February 27, 2015
The idea is good. Instead of Hollywood gossip, tales of slugging reporters, and bouts with Ava, why not write a book that focuses entirely on his output as a singer? However, the execution is about as bad as you can get. It is full of bad puns, clumsy sentences, non sequiturs, and any excuse to use a reference to a song lyric. He insults any rock-era musician or songwriter, despite the author's not looking older than mid-40's when this was published (sometime in the early 90's). How many people born after 1945 think of the Beatles as "kiddie pop"?Just to give you an idea of how bad this is, when discussing Neil Hefti, who after working with Frank wrote the Batman theme, he actually writes "Holy foreshadowing!" It's really too bad, because the author knows a fair amount about music--possibly getting a little too technical for non-musicians, but great for people who are musicians. And the facts that he's gathered from interviews are exceptional. It's just hard to believe that he could write this, read it, and still think "Yes! This is great writing!" And that the editor and publisher went along with it! If you ask me, this guy can't write a book.
Profile Image for Tim Gause.
12 reviews
February 19, 2013
I loved this book about Sinatra's music . The book also gives much deserved credit to all the great arrangers that made Sinatra great.
716 reviews3 followers
July 9, 2025
Detailed, maybe too detailed book on Sinatra's "musical Life". Friedwald discusses what made Sinatra a great singer, and his long and numerous concerts and record albums. I wish we could have had more about the particular songs and what makes them great instead of so much focus on the album arrangers/producers. Friedwald has the NYC hipster love of the complex and upbeat over the more popular and slow-moving. And we get the expected shots at Mitch Miller, Rock n' Roll and country music.

The author's also soft on the Record Industry. Sinatra more or less took over ownership and total control of his records around 1960 and that's when his decline set in. Friedwald suggests that's due to his cutting out the Record execs, who presumably "Knew what sold". I'd say thats more correlation than causation. Nobody stays on top forever, and jazz and Pop music in general had been declining since the mid 50s. Young people were listening to Rock n Roll. Cutting edge Black musicians had moved on to other musical forms.

Sinatra was 45 in 1960, and so was most of his audience. And the great pop music composers were even older. So, Sinatra didn't have a lot of good, new, material to sing. He had to go with crap like "Alfie" or belting out "Chicago, Chicago" or "I did it my way".
Profile Image for Ceste Stanly.
172 reviews6 followers
August 28, 2024
I have read at least 8-10 books about Sinatra, but I was elated when some1 in my Sinatra fb group recommended this 1. Unlike other bks about Sinatra, this 1 goes into minute detail about how Sinatra selected songs to record, who wrote them, who arranged them, how he found the arrangers, what was influencing him musically etc. Being a prof musician myself & a singer, I loved learning all this. It made me feel like I was actually there. I could only read 10 pages at a time though cuz the incredibly in depth analyzation really tired my brain. Looking forward to reading more by this author but need to take a break for at least 6 months to a yr
7 reviews1 follower
December 9, 2023
Certainly a well-titled book, as Will Friedwald deftly retells Frank Sinatra's story in song – while providing readers with a remarkable new understanding of the work, process, and fragile successes involved with singing. I don't know how many times I've re-read 'Sinatra! The Song is You,' and I seem to learn something new every time.
Profile Image for Gabriella Vegvari.
26 reviews
January 11, 2019
A tough slog for sure but very informative with interesting insights into the arrangers Mr. Sinatra worked with throughout his career.
Profile Image for Tom Santopietro.
Author 16 books21 followers
June 3, 2018
The definitive analysis of Sinatra's recording legacy and why he rates as THE singer of the 20th century. Friedwald discusses not just Sinatra's vocals, but also the arrangements and musicians who helped shape the breadth and depth of the classic Sinatra albums. Well written and packed with information and insight, this is a great read for Sinatra fans and anyone interested in "The Great American Songbook." Now available in an expanded and revised edition.
Profile Image for Stewart Summers.
23 reviews
December 14, 2012
This brilliantly researched book is epic in proportion. Mr. Friedland has served Frank Sinatra's legacy well...Sinatra the great recording artist.

We love Sinatra's recordings for many reasons. The quality, timbre of his voice, his unique phrasing and breath control. Those well written songs which were a marriage of great melody and lyric. His voice was a true vocal instrument.

I loved this book because I learned so much about those great recording sessions, the talented arrangers and great studio musicians who contributed to those outstanding recordings that will live on forever.

No gossip here. Thankfully!

PS- check out the Sinatra track "I Have Dreamed" from the album "The Concert Sinatra". Perhaps the greatest recording of all time...by anyone!
Profile Image for Eric.
35 reviews4 followers
August 3, 2015
With so many books focused on the tabloid aspects of Sinatra's life, I picked this up with the relief of knowing that it was a thorough examination of Sinatra the singer. It is that, but it's also a classic example of of "too much of a good thing." I mean, holy crap does this book get granular, to the point where it dissects how many ways Sinatra sings a particular syllable across the dozens of versions he cut. And it goes through this exercise for hundreds of songs, which leaves you too spent to care when you get to the good stuff about particular albums, arrangers, etc. A shame- this coulda been a contender, if it dropped a third of its weight.
17 reviews10 followers
May 26, 2011
Long, detailed, and opinionated. Focuses in the arranges and players.
Profile Image for Linda J. Sandahl.
29 reviews1 follower
September 29, 2016
A great biography of Frank Sinatra, the artist. This is not about movie stars or mobsters or divorces; it's about one of the most influential musicians of the 20th century.
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