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Playboy: 50 Years: The Cartoons

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For 50 years, Playboy magazine has showcased the world's best and brightest cartoonists. Their spectacular stable of artists includes luminaries such as Buck Brown, Jack Cole, Eldon Dedini, Jules Feiffer, Shel Silverstein, Doug Sneyd, Gahan Wilson, and hundreds of others. Hip subversives and sly revolutionaries all, Playboy's artists have continually proffered a sophisticated brand of humor sorely missing in other men's magazines. Now, Playboy celebrates its golden anniversary with this glorious collection of the finest and funniest cartoons. Handpicked by Hugh M. Hefner himself, the pages are filled with the distillation of the entire cartoon archive, offering insightful commentary on topics from the sexual revolution to relationships, money, and politics. More than 450 cartoons feature sweet young things, terrible tarts, winsome wives, suitors, and studs — a riotous chronicle of five decades of Playboy cartoons.

368 pages, Hardcover

First published January 1, 2004

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About the author

Hugh Hefner

320 books19 followers
Hugh Marston Hefner also referred to colloquially as Hef, was the founder, majority owner, editor-in-chief, and Chief Creative Officer of Playboy Enterprises.

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5 stars
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34 (31%)
3 stars
30 (27%)
2 stars
14 (12%)
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2 (1%)
Displaying 1 - 17 of 17 reviews
Profile Image for Chloe A-L.
282 reviews20 followers
January 10, 2019
Playboy cartoons are fascinating mostly because they’re thoroughly unerotic. They’re all suffused with this childish sense of giggling at titties. They’re supposed to be sexy and funny, at LEAST, but if anything they’re weirdly cowardly, never showing vulvas and extremely rarely showing penises. There are definitely genuinely erotic or pornographic comics, and these are in comparison just tepid and embarrassing. They aren’t even funny!
Profile Image for Julie.
16 reviews1 follower
March 11, 2008
i was just reading it for the cartoons lol
Profile Image for Andrew.
772 reviews16 followers
December 22, 2023
However one may view 'Playboy' magazine, its importance as a signficant pop culture text during the the last forty plus years of the Twentieth Century can't be denied. Aside from the obvious erotic content and the supposed 'philosophy' of High Hefner, one of the most important aspects of the publication was the integration of cartoons into its overall look. Playboy: 50 Years of Cartoons is a more than satisfactory visual summary of how 'Playboy' developed as a major avenue for cartoon artists to create a lasting impression on a wide audience. Whilst no 'MAD' magazine, Hefener's publication was an important platform for some of the funniest, wittiest and artistic cartoonists in America.

Playboy: 50 Years of Cartoons is built almost entirely around samples of the artwork of those who contributed their cartoons to the magazine. This isn't a problem per se, however it might have been beneficial to have some more detailed biographical and/or other supporting contextual material included in the book. Even some discussion points on specific cartoons might have elevated this title above the accessible yet limited constraints of the coffee table book. Yes, one can find pleasure at looking at the images, maybe laughing or perhaps indulging in a little nostalgia, or respond to the unique aesthetics of the artists in those examples of their work included herein. However, most readers will only find a passing engagement with this book on these bases. An expanded narrative accounting for the work and their composers might have given Playboy: 50 Years of Cartoons a longer and more meaningful impact.

When it comes to the cartoons they are invariably interesting both in terms of their style, humour and meaning. Yes, some of the jokes that underpin the illustratiuon are tired, elusive, sexist, or just unfunny. That doesn't mean they can't be valued or analysed as visual texts, and as seen in Playboy: 50 Years of Cartoons there can be lots to be read from the illustrations. Cultural and social attitudes from the 1960s to the mid 2010s are strongly represented, and one can definitely see how the cartoons reflect both what was predominant at the time of composition, and how things have changed since then. The sexual politics of the cartoons are also readily apparent, and this is perhaps the most important area for consideration. There is no doubt that many cartoons publisher in this book represent outmoded and chauvinistic constructs; this is, after all, a compilation of cartoons from a men's magazine that was aimed at a demographic that were prejudiced about many sexual issues. One has to be both aware of this and at times perhaps let through some of the more non-PC efforts through to the keeper. Jokes don't always stay funny and what was thought of women, of non-straight people has changed since many of these cartoons were first published, so their value may be more related to what they tell the reader about the gap between then and now.

Having said all of that, there is the pleasure to be had at looking at the cartoons and enjoying the artistry of each illustrator. Gahan Wilson's works are perhaps the most memorable in that not only are they alienated from the general sexual themes of the other cartoonists' works, they are still funny and very much in the tradition of the American Gothic. Wilson's use of line and colour is striking, and when aligned with the grotesque or monstrous idea within each cartoon they are highly effective. It might be said that Wilson is the true genius of Playboy's cartoon alumni in that he wasn't constrained by the need for his drawings to be titillating.

There are some other artists represented in Playboy: 50 Years of Cartoons whose work is enjoyable and unique. Edmond Kiraz's cartons are highly stylised and perhaps more interesting because of this than because of the supposed humour they depict. There are the Rubinesque volupturaries of Eldon Dedini and curvy women of John Dempsey. Then there is a small section dedicated to the absurdist work of Shel Silverstein, whose drawings and poems about imaginary animals is in the best traditions of Edward Lear and Lewis Carroll.

The underpinning construct of Playboy: 50 Years of Cartoons is that this is a book of supposed adult cartoons with a (mostly) sexual angle. Anyone offended by such a central raison d'etre for a book will not be happy to read it. Those on the other hand who are less biased, who are perhaps intrigued by cartoon art, by the social, sexual and political attitudes of those who read 'Playboy' in its hey day, and those who are interested in revisiting their own furtive relationship with Hefner's magazine will find plenty to like about this book. Me? I liked it, but I am also aware of its limitations.
Profile Image for Jacob.
474 reviews6 followers
December 4, 2017
The best part of this collection is the essay that introduces it. Short, but talking about the impact of censorship on comics and cartoons--it's a fascinating history. It also leaves a lot unsaid, quickly giving way to a mishmash of contextless cartoons: New Yorker-style single images with captions, some strips, and the occasional multi-page storyline.

While today Playboy is a bit of a quaint idea, for the pre-Internet world it was a ground-breaking skin publication. The emphasis on serving the male gaze is inherent within these, with a solid "most" of the comics featuring at least visible nipples, if not full on nudity. There is a certain erotic sensibility to paging through this collection.

That said, the most important thing of a comic is how funny it is. And that is where I struggle the most with this collection. I laughed out loud a couple of times. Appreciated some others. But mostly they were either boring (going for the low-hanging gender politics fruit) or something that I couldn't make heads or tails of. Either they required a pervier mind than mine, required historical/political/social context that I don't have, were part of Playboy in-jokes I wasn't privy to, or were simply bad comics.

Ultimately, this seems like a collection that is more for someone who has spent time in their life reading and enjoying Playboy magazines, who wants that nostalgia kick. It is not for someone like me, who hasn't cracked open a Playboy in his life and thought perhaps some sexually bold comics might be amusing.
Profile Image for Colin Murtagh.
625 reviews7 followers
July 17, 2022
I do like my cartoons, and while this is not the New Yorker, or even Private Eye there's still a fair amount to enjoy here.
While the vast majority do revolve around sex, and we'll come back to that, there are a few other little things hidden away. There's a King of the Hill, a Fabulous Furry Freak Brothers, a lot of Gahan Wilson doing monsters, a really odd CSi does Enron strip and even a Shel Silverstein series.
Saying that the vast majority are sex cartoons. A fair few just wouldn't fly nowadays, the boss and secretary is not really an acceptable trope any more for example. Some of them, yes I'm looking at you Vargas, aren't really gags and are just excuses to draw the female form.
Given this is Playboy, and it's an American publication, it has the usual weird American hang ups with the entire idea of bodies. There is nothing that could be considered erotic, and really nothing that could be considered pornographic. Heaven forbid.
If you've an interest in gag cartoons, you should enjoy this, if not, it's probably not for you
Profile Image for Geoffwood.
100 reviews1 follower
January 21, 2019
Kinda hard to review. The work of Gahan Wilson in particular is unqualified genius and really has nothing stylistically in common with anything else. Jack Cole and Shel Silverstein and probably other people I forget do some good work but then there's still like 50-60% of the book that's somewhere from amusingly dated to painfully dated to painfully somehow someone thought it was funny this century. Absent objective signifiers like technology and politics, I'd swear there was nothing published after 1980, but I think we hit late W if not Obama in here. Peak noodlescratcher goes to the licensed King of the Hill strip, the author of which, to his credit, seems to have watched fully twos of episodes to so masterfully capture the essence of the show and the character names.
1 review
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July 4, 2025
I'm a 73yrs old male. I grew up with Playboy. All of my friends did. Before we hit that grand age of eighteen we all traded, & swapped back and forth those treasured issues. I remember when Playboy featured their first pair of twins in the centerfold! Which is why I have to give this wonderful volume only a single Star!
To us, the captions were just as important as the artwork. We only read scattered issues. So, while I still remember the captions of those single panel cartoons I saw. I feel like I am being robbed of the full joy these cartoons were meant to empart.
I have a PDF version of the book. Maybe the captions are in the print edition. If the captions are not in the print edition I cannot recommend this book.
This entire review has been hidden because of spoilers.
257 reviews
August 17, 2023
A few great cartoons, and certainly some great cartoonists, but a haphazard presentation, with no publication dates, and no apparent rhyme or reason to the order. No commentary or biography of the cartoonists either.

So we get some fine examples from Gahan Wilson, Jack Cole, Doug Sneyd, et al, but the randomness is frustrating.

At some point, some ambitious publisher will do a comprehensive multi-volume collection, with at least some minimal exposition, but until then, this will have to do.

(Gahan Wilson's Playboy cartoons are presented in a much better collection from 2010, but that out of print collection will set you back a few bucks.)
Profile Image for Ryk Stanton.
1,721 reviews16 followers
January 18, 2020
Well, it's what I expected it to be, so I gave it three stars. But it's not a book I'd personally want to have on hand. Free from Hoopla was okay.

What struck me the most is how our perception of what's acceptable has changed, and how unfunny something that used to be considered funny has become.
Profile Image for Heidi Kirsch.
211 reviews1 follower
March 7, 2019
So dated and with all that's going on, too many of these have an uncomfortable male dominance
Profile Image for Ietrio.
6,949 reviews24 followers
June 11, 2019
Interesting from a documentary standpoint. The techniques have changed. The humor here might be unacceptable for 2019. And the quality of the jokes is quite mixed. Some are hilarious. Some are not.
Profile Image for Jim.
156 reviews2 followers
January 23, 2023
I enjoyed this book. The comics aren't too raunchy, and the editors put a nice cross section of humor across the decades. Anyone who's a fan of Playboy comics will appreciate many of them.
Profile Image for Mike Violano.
352 reviews18 followers
August 21, 2014
A fantastic collection of cartoons by some of the masters like Gahan Wilson and Shel Silverstein and long time contributors to Playboy like Eldon Dedini, Doug Sneyd and Erich Sokol. Some are a product of their times and mores others are truly timeless. A great chronicle of the humor and art that Playboy has promoted since the 1950s.
Displaying 1 - 17 of 17 reviews

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