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What's So Funny?: A Cartoonist's Memoir – The Witty Biography of a New Yorker Artist, Family, and Creative Life

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“David Sipress’s engaging, illuminating, and hilarious memoir will perhaps clarify what dark forces are at work when it comes to becoming a cartoonist rather than a podiatrist, a billionaire tech mogul, or someone who is deeply into collecting owl figurines. And if it doesn’t, you will love it anyway.”— Roz Chast From a longtime  New Yorker  staff cartoonist, an evocative family memoir, a love letter to New York City, and a delightful exploration of the origins of creativity—richly interleaved with the author’s witty, beloved cartoons. David Sipress, a dreamer and obsessive drawer living with his Upper West Side family in the age of JFK and Sputnik, goes hazy when it comes to the ceaselessly imparted lessons-on-life from his meticulous father and the angsty expectations of his migraine-prone mother.  With wry and brilliantly observed prose, Sipress paints his hapless place in the family, from the time he is tricked by his unreliable older sister into rocketing his pet turtle out his twelfth-floor bedroom window to the moment he walks away from a Harvard PhD program in Russian history to begin his life as a professional cartoonist. Sipress’s cartoons appear in the story with spot-on precision, inducing delightful  Aha!  moments in answer to the perennial question aimed at Where do you get your ideas? 

336 pages, Hardcover

First published January 1, 2022

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David Sipress

17 books10 followers

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Displaying 1 - 30 of 61 reviews
Profile Image for Linden.
2,108 reviews1 follower
October 4, 2021
Sipress offers a uniquely entertaining memoir composed of cartoons and text. He tells of growing up in New York City in a somewhat dysfunctional family, dropping out of Harvard, and following his inclination to draw instead of studying Russian history, much to the dismay of his parents. Thanks to Netgalley and the publisher for this ARC.
Profile Image for Susan.
886 reviews5 followers
May 26, 2022
What a wonderful book! I don't know the author/cartoonist although I do read the New Yorker on occasion so must have seen his cartoons. The book is witty, charming, funny and sad all at once.
Profile Image for SundayAtDusk.
751 reviews33 followers
March 8, 2022
In the beginning, this book reminded me of the "Metropolitan Diary" column in the "New York Times". Great! That is one of my favorite features in the paper. Only, those diary entries are positive types, whereas this memoir was somewhat melancholic. Yes, it has funny cartoons, but David Sipress is wrestling with his family memories and members in a sad sort of way, complete with accounts of visits to his therapist. Is it really the reader's business all that went on in his family? Is it really all that interesting to those outside of his family? Personally, I think not. This is more of a private diary memoir than one a general public reader will likely identify with and appreciate.

(Note: I received a free e-ARC of this book from NetGalley and the author or publisher.)
332 reviews
July 11, 2022
The author responds to the question of where he gets his cartoon ideas from. In short, many of them come from his parents and sister, though you may feel you end up learning more about them than you wanted to.

He had a Jewish father who grew up in grinding poverty in Tsarist Russia who emigrated with his family to New York City, where he would eventually become a highly successful jeweler, and a Jewish mother from the Deep South, and an older sister who would turn out to have severe mental problems. He talks about how he always wanted to be a cartoonist for the New Yorker magazine, though it took decades before he succeeded, though he pursued a degree in Russian history but quit before graduating, much to his father's displeasure. In the end, many incidents in his family life ended up as jokes in his cartoons. Not a very happy story, when you think about it.
Profile Image for Armand Rosamilia.
Author 257 books2,745 followers
August 15, 2022
It's the autobiography of a cartoonist, and the cartoons spread throughout the book are delightful. They tie into whatever experience he is talking about, and not all of them are funny or nice. His life wasn't an easy one but he made the most of it and had a few laughs along the way. Some really funny and really sad parts to this well-written book!
Profile Image for BOOKLOVER EB.
910 reviews
March 8, 2022
In "What's So Funny?" David Sipress regales us with amusing and poignant anecdotes about his childish misdeeds, dysfunctional family, and dream of becoming a cartoonist. While growing up, David felt smothered by his neurotic mother, Estelle, and overbearing father, Nathan. David's dad was a self-made businessman who frequently lectured his son about the value of money and the importance of living up to his parents' expectations. Sadly, David's older sister, Linda, had serious emotional problems, and she often quarreled with her mother and bullied her brother. It is fortunate that, early on, David realized that cartooning could provide him with a creative outlet for his feelings.

Hundreds of Sipress's cartoons have appeared in the New Yorker. However, before he became an established contributor, the magazine's staff routinely rejected his submissions. It is difficult to imagine why, since his cartoons are hilarious, clever, and well-crafted. Most of them are a magical blend of whimsical drawings and beautifully written captions. I found myself laughing—often out loud—at the people and situations he depicts, and I admire his empathy for those who struggle to make their way in a world that can be cruel, baffling, and unfair. Humor and a sense of perspective are two qualities that help us stay sane during tough times. Sipress's insight, wit, and considerable talent have helped him thrive professionally and personally. He dedicates this entertaining and bittersweet memoir to his wife, Ginny, a "loving partner in all things." Furthermore, he says, "I am deeply grateful to my therapist (you know who you are) for helping me make sense of my family, not to mention, myself."
Profile Image for Alinna.
75 reviews2 followers
June 14, 2023
I picked this up on a whim as I’m trying to read more memoirs and biographies, and I’m so glad I did. I loved Sipress’ writing and how he shared his memories with both humor and vulnerability. The cartoons within the book really took it to another level and were examples of a picture being worth a thousand words.
Profile Image for Rex Hesner.
Author 2 books3 followers
January 27, 2025
A long-time contributor to the New Yorker, Cartoonist David Sipress shares the quixotic twists and turns of an artist's life in New York City. Sipress candidly shares the fascinating oddities of growing up in a comfortable but eccentric family on the Upper West Side of Manhattan. We follow his winding path through academia, then a stint as a sculptor, before turning to cartooning--all told with a wry sensibility. Along the way, Sipress educates the reader about his approach to cartooning and his experience in that industry, including decades of rejection from the New Yorker. As an aside, my writing partner Phil Witte and I interviewed Sipress for our book about single-panel cartoons, Funny Stuff: How Great Cartoonists Make Great Cartoons.
312 reviews2 followers
April 1, 2022
I had never heard of David Sipress but decided to read the book based on some positive reviews. I was glad I read it. The cartoons were a wonderful addition to the text and always spot on. The book was very funny in parts and sad in others. I loved hearing his dad's responses to some of life's challenges. I found them funny and poignant just like this book.
Profile Image for Michael Hassel Shearer.
105 reviews8 followers
December 19, 2021
What’s So Funny? By David Sipress
Mr. Sipress is a cartoonist who has made after 20 years of trying into the big time as one of the primary cartoonists for The New Yorker. This is a book about his life and it is filled with his cartoons that fit the story he is telling at the time. He is not only good at drawing but also writing. I very much enjoyed reading this book as well as seeing and learning about the art of cartoons. To begin with I could relate to the over-arching story even though I am not: (1) Jewish, (2) from New York City, (3) a lover of the Yankees, (4) a drop out from Harvard Grad School or (5) have a psychotic sister. Instead, I was raised a catholic, Bostonian, obviously the Red Sox, have a Ph.D. and my two sisters are both quite nice. So how can I relate?
The real story is his father or came to America as a small boy from Russia and succeed through his hard work and believed that life we not meant to be fun. Life like work was to be endured and success was measured by the accumulation of stuff. This was not my father but like Mr. Sipress’s father-Nat, my father had a very hard time expressing his love. And this book is just about this father-son relationship full of love that can not be expressed. In Mr. Sipress’s case only through some of his cartoons which his father thinks are foolish and something only a child should do.
I can not recommend this book more highly for anyone who knows what it is liked to not be hugged or has trouble hugging. And at the same time it is a highly amusing visual read.
Profile Image for Nan.
721 reviews35 followers
October 17, 2022
David Sipress, staff cartoonist for The New Yorker, reflects on how growing up with an overprotective mother, overbearing father, and unstable older sister impacted his life and career. Illustrated throughout with Sipress's cartoons, What's So Funny? is well-written with pathos, humor, and heart.
436 reviews1 follower
June 9, 2022
This memoir of a New York Times cartoonist held my interest right from the beginning. Yes, it is a memoir, but seems to be a memoir mainly of the author's relationship with his family, especially of his relationship with his father.
The audible version of this was great - the narrator did a good job of capturing the voice of the author's father.
The author's account of growing up in this family was remarkably honest and moving. I don't know if he would label it such, but I saw it as a kind of love letter to his father who played out as a major character in the book.
Profile Image for Katie.
282 reviews
April 24, 2022
Received this book from Goodreads giveaway.

Even if you just pick up the book to read the New Yorker cartoons, it is worth the time. I would give this an extra plus if I could. A really nice read about struggling for approval of a misunderstood career from "old world" parents and culture.

The only piece missing is the sketches his dad made of the jewelry pieces.
Profile Image for Steven Meyers.
600 reviews2 followers
August 4, 2023
“STILLING HIS FLUCTUATIONS”

‘What’s So Funny?’ had strong appeal for me because I too am a professional cartoonist who is primarily known for creating editorial cartoons in Maine’s largest newspaper for a little over thirty years. The 76-year-old Mr. Sipress’s cartoons, especially his work in New Yorker magazine, have a much wider audience than mine. He’s a big fish while I’m a teeny-tiny minnow in the cartoonist pond. Mr. Sipress spent 25 friggin’ years submitting cartoons to New Yorker magazine and being rejected before they accepted one of his pieces. He then became a regular contributor with over 700 cartoons printed in the publication. I am in awe of Mr. Sipress’s two-and-a-half decades of persistence in getting his work finally accepted by New Yorker magazine. I can say with absolute certainty that this 63-year-old Maine cartoonist would never have spent so many years trying to reach that magazine mountaintop. The book was published in 2022.

‘What’s So Funny?’ begins by skipping around the author’s childhood while growing up in New York City. Every page covering his childhood either made me smile or laugh out loud. His acerbic deadpan humor is much to my liking. Mr. Sipress’s therapist called the author’s cartooning efforts to “still his (mental) fluctuations.” Cartooning is a form of therapy. Mr. Sipress and I have that in common. One of the charms of ‘What’s So Funny?’ is showing through personal stories how he not only developed into a cartoonist and how some of his pieces were directly taken from his own experiences, but it also portrays his complex emotions in dealing with his parents and sister, Linda, who was six-years-older than him. There are some dark pieces of humor in the book. They include such topics as their family’s celebration of both Hanukkah and Christmas as practicing secular Jews; scoring high on an IQ test; handling money and discovering the value in lying; his dad being a Russian immigrant; their dad’s jewelry store being robbed at gunpoint; the assassination of President John F. Kennedy; his interest in Russian history; the mystery behind his dad’s total separation from his relatives who also lived in New York City; his courtship and marriage to Ginny Shubert; and the eventual death of his dad, mom, and sister. It includes many of his cartoons and a handful of black-and-white photos that are sprinkled throughout his story. The memoir also includes a bit of profanity including the f-bomb.

The previous book I read was quite depressing. For my next reading adventure, I needed something that would make me laugh. ‘What’s So Funny?’ did the trick, but the memoir is not all guffaws. It also dealt with some sad situations. The late Clare Boothe Luce, writer/politician/U.S. ambassador/wife of TIME magazine publisher Henry Luce, once said, “Autobiography is mostly alibiography.” Well, it’s safe to say that Mr. Sipress poked that quote in the eye. He had no reservations about exposing his less-than-admirable traits, especially when he was a child. ‘What’s So Funny?’ is a heartfelt intelligent memoir that is not only for people interested in cartooning.
137 reviews1 follower
May 24, 2022
Really good book about a cartoonist's life growing up in NYC. The son of a jeweler and his wife. The mother is an attentive mother, the family is Jewish and parent loving but firm with their children. Not unlike most parents at that time. Attention was paid to the children, they were loved and the expectation was that the kids would be good kids. They are a nice, conservative family growing up whose mother tends to the home and children and the father brings home the paycheck. David is born about 1954 so that sets the stage in timing.

As time moves on David's father is always immaculately dressed for work 6 days per weekand somehow acquires sophistication despite being from difficult circumstances growing up. He is hardworking, obviously truly intelligent and so is his wife. The family lives in a nice enough apartment building and neighborhood. It weaves into the book common sense rules, mores of the time and a sense of neighborhood community.

David is the son of a man who immigrated from Russia as a young child who never went to school after 5th grade (had to work to contribute to his own family even as a child). This man grows up and somehow becomes a modestly successful jeweler and raises (along with his wife) David and his 6 year older sister Linda. Both David and his sister went to Harvard and also top tier graduate schools. Quite the accomplishment when you realize one generation earlier, his father was a small child at Ellis Island emigrating with poverty stricken parents and forced to work at the age of probably 11 years old. His parents value education, hard work, family. These are good things always.

Linda is bi-polar at a time when things like that probably weren't discussed and in many ways overtook the attention of the parents with all "her needs". And the needs became more pronounced as she got older. In particular her father who was pestered many times per day even as an adult woman. David grows up to be a successful cartoonist for the New Yorker magazine after persevering for many many years trying to get his first cartoon published in that periodical. He was successful in other magazines prior to the NYer.

I would read another David Sipress book as he is an easy author to read and he has a wonderful turn of phrase and thinking creatively. His cartoons are very clever.
1,597 reviews41 followers
May 15, 2022
in honor of the annual merit pay review coming up shortly at my job, I'll say that this book not only "meets expectations" but exceeds them. That is, yes, he's a funny writer, and the reprinted New Yorker cartoons are often hilariously on the mark for illustrating whatever situation he's recounting at that point in the text (persistence pays apparently -- after many years of trying to get his first one published, he now has 700+ cartoons in the magazine -- don't know if he's regularly autobiographical with them, as only a small fraction of that number are included here).......

..........but the book is much better than just an amusing take on the cartoonist life. Fascinating, often sad, story of his upbringing in NYC in a not-highly-observant Jewish family. He bumps up against his parents' (esp. Dad) various neuroses, recaps their conflicts and his own foibles (e.g., dropping out of grad school on the spot during a tough final exam and only later thinking about what this might mean for parental financial support, not to mention his student deferment from Vietnam War).

There's a tragic story involving a sibling that I probably shouldn't spoil, but will just leave it that his account of his and his wife's attempts to come to terms with what happened is very moving.

all in all, very strongly recommend. Don't let the gun on the cover scare you off (kidding, it's a family picture from when he was about 6 showing him posing menacingly with a toy gun -- times have changed since more or less every little boy wielded those on the regular).
Profile Image for Laura.
1,682 reviews31 followers
September 3, 2023
The cartoons in this are really funny - I'd love to look up more of Sipress' work. His family's story of immigration and life in NYC are fascinating, and his childhood is described with humor and poignancy. I'm so glad he shared pictures of his family - what a treasure. I thought his interactions with his father towards the end of his life were hilarious- describing his birth as "mistake" instead of a happy accident and constantly asking him if it wasn't too late to consider Russian history as a career. Having an adopted child with mental illness, it makes me wonder how the other kids will describe their childhood as adults. I also wonder if Sipress has children of his own, because oftentimes you look back on parenting with a softness and understanding when you have done the hard work yourself that is lacking somewhat here. (Although - only he knows what it was actually like). It's never specifically addressed, but I'm so curious why his father cut himself off from his family! And I wanted to tell him - YES! Your dad did that stuff because he loved you, even though it was confusing and hurtful! Overall, it was a good read, great comics, and an interesting glimpse into NYC in the 20th century.


Won this in a giveaway - Thanks to the publisher for the copy and goodreads for hosting the giveaway!
Profile Image for Rachel.
2,176 reviews34 followers
July 14, 2022
The first, and sometimes most important, relationship in our lives is with our parents. However, rarely do we read works that show that relationship from both points of view: that of a child about a parent and then a parent about a child. That’s what made reading “What’s So Funny? A Cartoonist’s Memoir” by David Sipress (Mariner Press) and “Raising Raffi: The First Five Years” by Keith Gessen (Viking) for this review so much fun. While the two memoirs don’t completely mirror each other, Sipress’ difficulties with his parents were in some ways answered by Gessen’s issues when dealing with his young son. I could imagine Sipress’ father talking about his son in the same way Gessen speaks about Raffi, and wondered how Gessen’s son will view his father’s essays when he is as old as Sipress.
See the rest of my review at https://www.thereportergroup.org/past...
Profile Image for Ivy Digest.
176 reviews
August 14, 2022
David's stories will resonate with Jews, Russians, and immigrants as his family is all three. I was intrigued to read this because of his funny cartoons. I loved how he stood up to this wealthy dad and dropped out of Harvard to pursue the arts. Every aspirational parent's nightmare.

As with many humorists, David's family life has repressed drama, unspoken shame, and distressing secrets marked by anxiety, depression, and angst. He describes scenes with objective hurt as he recounts his conversations with his therapist. At least he was wealthy enough to afford psychological help and the leisure time to imbibe substances in Europe.

Sometimes, David relates how he used his pain to produce cartoons, but it's mostly chronological events. It would've been more entertaining if he added more cartoons because the comedy was lacking. Maybe David needs more time and distance to find the funny.

@IvyDigest
Profile Image for Rosemary.
1,272 reviews
April 6, 2022
I absolutely loved this book! It is the author’s story of growing up and becoming a cartoonist, despite his father’s strong disapproval…told in words and cartoons, with poignant, honest truth and humor. The contrast between the little boy on the cover, with his sister and mom and dad, with his holster and six shooter with the author photo on the endflap, arms crossed, wearing a gold wedding band and a wry, calm smile began my curiosity for his story in between. He led a life full of his father’s aphorisms, don’t count your chickens, money doesn’t grow on trees, the proof is in the pudding; growing up with love but such a heavy load of expectations, familiar to many of his readers. I nodded and smiled and enjoyed this thoroughly and can’t wait to recommend it to family and friends!
Profile Image for Marleen.
667 reviews5 followers
August 23, 2022
A very entertaining story about becoming a cartoonist. David Sipress was a student of Russian studies when he suddenly realizes he is not having fun and precipitously quits his graduate program to pursue his passion, cartooning. Of course his immigrant father thought he was throwing away his future. In order to create some distance from his NY family, he begins working in Boston but he eventually makes it back to the Big Apple. David is very clever and much of his humor is based upon his non-observant, Jewish American experiences and his father's career running a high end jewelry shop. His mother is always busy cooking and cleaning and fighting with the elder, emotional daughter. It provides enough drama in the family so that David's role is to be as little trouble as possible.
961 reviews7 followers
March 19, 2022
On the positive side: the placement of the cartoons was spot-on, perfect additions to the situation being discussed. The cartoons themselves are terrific. On the negative side: too much repetition and too much of re-telling of what he told his therapist. I think a good editor could have pared this down considerably, and we would still have had an insight into how Sipress grew up and how he comes up with his wonderful cartoons. In truth, I'm not a fan of memoirs, and perhaps that's why I'm not enthusiastic about this one. I heard Sipress on the radio being interviewed, and that's what made me get his book. It sounded like it would be interesting and amusing. It was, but only to a point...
1,018 reviews13 followers
March 23, 2022
Thank you to the author, Mariner Books and NetGalley, for an ARC in exchange for an honest review.

This memoir was by turns interesting, amusing and melancholic, and gave me a lot of insight into how the author's mind works to come up with the cartoons he does so well. A dysfunctional family certainly helps, as evidenced by the stories about growing up in the Sipress family. Some of this made me wonder whether certain information might have better remained between the author and his therapist - a bit more editing might have been a good thing. The cartoons that are included are great, and it's amazing how certain aspects of the story are emphasized through their inclusion.
198 reviews2 followers
April 27, 2024
The author always wanted to be a cartoonist and has been published in The New Yorker over 700 times. The book is full of his cartoons, along with the stories that helped him to create them. The stories are about his life. His parents emigrated to the USA from Eastern Europe. His father became a well-known jeweler in NYC. He definitely did not think that cartoonist was a career. When David dropped out of university, he didn’t tell his parents for quite a while. They were not amused. The memoir is about his life, his parents, his wife, his sister. It is also about cartoons, how he gets the ideas, how they evolve. He writes well and the cartoons are funny. Worth reading.
911 reviews10 followers
March 29, 2022
When I signed up for Goodreads Giveaway of this book, I had never heard of David Sipress, but the book sounded good. Once I won the giveaway and received the book and thumbed through it, I realized I had seen, and laughed at, a number of Sipress' cartoons. The book is both funny and heartbreaking. Sipress demonstrates what most of us deal with in the--life-long- process of growing up: finding our own way in life without losing everyone we love. Thanks to Goodreads and Mariner publishers for this copy of the book.
Profile Image for Rose.
752 reviews
April 11, 2022
Growing up in the 50's, 60's and 70's in New York City. David Sipress tells his life story from the funny to the serious. Anyone growing up in this timeframe can relate to David's story. His parents did not think that being a cartoonist was a career. It shows the struggles when growing up and how our parents affect who we become even if we don't realize it.
This was a very enjoyable book and I would recommend this memoir.

Thank you to #goodreads, @DavidSipress, and @HarperCollins for a copy of this book.
214 reviews2 followers
June 22, 2022
Very entertaining memoir written by a Jewish cartoonist from NYC. His dream was to draw cartoons for the New Yorker but his hard driving father and over protective mother had other hopes for him. He is open about his life and difficulties he and his family faced throughout his childhood and adulthood. Plenty of great cartoons scattered throughout, most having to do with his family and their place in his life at times of stress and frustration. If you are somewhat familiar with NY all the better for your enjoyment.
936 reviews2 followers
April 26, 2022
Finished What's So Funny?: A Cartoonist's Memoir by David Sipress. I have a life long fascination with cartoons and cartoonists. A review of this book caught my attention. Sipress was a graduate student in Russian Studies when he took a hard career turn to his dream job, drawing cartoons. The child of Jewish immigrants, he grew up in Manhattan. I found his story entertaining and also got a glimpse at the mind of a cartoonist.
Profile Image for Carol.
25 reviews
June 11, 2022
I enjoyed this memoir very much. It reminded me of a multilayered painting—the writer revisiting familiar areas, changing them, creating perfect imperfections. I was surprised by how familiar his very personal story felt, but this writer has a way of drawing the reader in almost imperceptibly, but persistently. And the cartoons? Gold.
Profile Image for Robin.
2,190 reviews25 followers
July 28, 2022
What a beautifully told life story! I was drawn in right away and didn't want to stop reading. Having it interspersed with his New Yorker cartoons was a nice bonus. I so admire people like David Sipress who can recall so much detail in their lives. Just amazes me to no end. If you've ever looked at New Yorker cartoons, and wondered about their creators, this book is for you.
Displaying 1 - 30 of 61 reviews

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