From Birth to the 1970s

by Tim Pilcher

  Hefner started what would become a vast empire with a mere $8,000, producing the first issue of Playboy on his kitchen table. To save money he wrote the majority of the articles himself, and reworked public-domain short stories. He took all the strengths of Esquire, even copying its “Esky” mascot concept and turning it into the Playboy Bunny.

  The shrewd marketing strategy transformed the Bunny icon from a dopey adolescent idea to a symbol of sophistication and style. Playboy undoubtedly made girlie mags reputable, and this respectability lured top cartoonists.

  Hitting newsstands in December 1953, Playboy #1, simply subtitled “Entertainment for Men,” carried no cover date because Hefner was unsure when or if he would be able to produce another. He needn’t have worried—Playboy blew all the competition out of the water. “I never intended to be a revolutionary,” Hefner recalled. “My intention was to create a mainstream men’s magazine that included sex in it. That turned out to be a revolutionary idea.”

  Rival publisher Roscoe Fawcett noted: “We did wonderfully with True—the largest selling men’s magazine until Playboy came along and killed us with the advertising dollar.”

  Hefner consciously cultivated the “Hef” persona—a carefree, gadabout lounge lizard who would become synonymous with his pipe and pajamas. In reality, Hefner was a workaholic, staying up late working on the latest issue while the parties raged on around him.

  This extremely risque gag by “Andrews” comes from one of Playboy’s longstanding competitors, the down market and defunct Adam magazine. The Sixties cartoon has the woman asking “Why don’t you ever play the flip side?” using the vinyl record as an allusion to anal sex.

  “What did you say you stocked this pond with?” This beautifully rendered illustration by Ernst shows that most of the mens’ magazines from the ’50s and ’60s had a high standard of full page erotic and saucy gag cartoons.

  By July 1957, Playboy was bragging that it was “the most imitated magazine in America.” Certainly there were many pretenders to the throne, including The Gent (“An approach to relaxation”), Gay Blade (“For men with a zest for living”), The Dude (“The magazine devoted to pleasure”), and Rogue (“Designed For Men”).

  Hefner was a man with a constant ear to the cartooning ground, seeking out talent in the most unlikely places. Hef had studied anatomy at the School of Art Institute of Chicago, where Gahan Wilson—soon to become a Playboy mainstay—also honed his illustrating craft.

  Because of his love of the medium, cartoonists warmed to Hef instantly and he was gently ribbed and drawn into many strips and gags by artists as diverse as Will Elder, Harvey Kurtzman, and Jules Feiffer, and even “guest starred” in Mike Judge’s King of The Hill strip specially created for Playboy.

  The magazine continued to grow, and by the start of the ’60s, Playboy was making $3 million a year. But, as usual, the law was never far behind, and Hef was arrested in June 1963 on obscenity charges for the Playboy pictorial, “The Nudest Jayne Mansfield.” However, the ever-eloquent Hefner argued such a tight case for freedom of expression and anti-censorship that a hung jury voted seven-to-five in favor of his acquittal.

  This exceptionally drawn cartoon from Gay Book in October 1937 set up the archetypal boss and sexy secretary scenario that would be played out in endless gag cartoons over the following decades. The simple caption reads, “Is that you dear? Go to hell!”

  Misogynistic cartoons were the mainstay of men’s magazines right up to the mid ’70s (and beyond, in some cases). This one’s caption reads, “Wha-what happened? …Where’s the party?… Wh-where am I?” Implying that date rape is something to joke about.

  PLAYBOY’S ARTISTIC GENIUSES

  In addition to those already mentioned, work by legendary creators such as John Dempsey, Jack Davis, Edmond Kirazian, B. Kilban, and many other talented cartoonists graced the pages of Playboy, all enhancing the magazine and its reputation. “Playboy’s visual humor helped to define the magazine, its lifestyle, and its sexual politics for half a century,” reminisced Hefner in his introduction to Playboy: 50 Years of Cartoons. “I cannot convey the personal pleasure I have had in revisiting a full half century of Playboy’s illustrated humor.”

  And it wasn’t just gag cartoons that filled the pages of the magazine—there were sequential strips as well, by Frank Thorne, Gray Morrow, and, more recently, by Spanish artist Juan Álvarez. Even legendary underground cartoonists Skip Williamson, Jay Lynch, and Art Spiegelman provided strips, and Gilbert Shelton did a fully painted Fabulous Furry Freak Bros. special in 1974.

  As Hefner’s empire grew, he obviously had to relinquish certain duties and delegated the care of cartoonists to Michelle Urry. She was the perfect choice because, as a child, she had collected comic books rather than dolls. After graduating from UCLA and running a dress shop, she moved to Chicago, taking a low-level staff job with Playboy in the late 1960s. By 1971, Urry had become the magazine’s cartoon editor, holding the post for 35 years until her death in 2006 and making her the longest-serving Playboy staff employee. On learning of her death, cartooning genius Jules Feiffer described her to the New York Times as “the Mother Superior to cartoonists.”

  Pierre Davis’ cover to a 1972 edition of the bizarrely named Sex to Sexty, which featured classic erotic artists such as Bill Wenzel and Bill Ward. The magazine was a mix of crude jokes and gag cartoons.

  Possibly the greatest single entendre gag cartoon ever, from Gent magazine. The caption simply reads: “I know just what you’re going to say, Mr. Howell.”

  Doctor Dare and the Spear of Destiny, from Penthouse Comix #6, was Gray Morrow’s homage to pulp novels like Doc Savage and Captain America. The strip was later collected into a graphic novel. Morrow also drew an erotic strip for Playboy, called Vaginella: Dream Girl of the Starways, which was a sexy sci-fi spoof written by Jim Lawrence.

  DOUG SNEYD

  Canadian artist Doug Sneyd was already an established textbook and magazine illustrator (and editorial cartoonist) when he took a business trip to Chicago to drum up business in 1963. He visited the Playboy offices where it was suggested that Sneyd produce one-off gag cartoons for them, rather than the editorial illustrations he was pitching for. Initially, the artist was reluctant, but when he discovered how much Playboy generously paid cartoonists he started a relationship that would span over 45 years.

  As well as writing his own gags, Sneyd worked with a team of writers, including Rex May. “Some gags are best drawn by me… others are best drawn by Doug Sneyd or some other fine artist,” explained May in a 1995 Smithsonian interview. May gave the example of a woman turning down a marriage proposal, with a caption stating, “It would never work, Rodney. You’re a Benny Hill person and I’m a Monty Python person.” “If I (drew) that, it would be mildly amusing,” said May, “But Doug drew it elaborately, with a beautiful woman and a beautiful setting, and the absurdity worked so much better.”

  Many of Sneyd’s roughs would be sent out to other cartoonists to fully render, influencing a whole generation around him. His cartoons had a strong, clear composition, lovingly rendered in layers of watercolor washes, and delicate transparencies to create depth and luminosity in the work.

  Never one to rest on his laurels, Sneyd simultaneously had his own news cartoons—Doug Sneyd and Scoops—syndicated in North American newspapers for nearly 20 years.

  Sneyd’s standing in the Canadian pantheon of illustrators is high, and he was a founding member of the Canadian Society of Book Illustrators, as well as belonging to the National Cartoonists’ Society and the Association of American Editorial Cartoonists. 24 of his full-page color Playboy cartoons are among an impressive collection of 229 of his works stored in the National Archives of Canada in Ottawa.

  A preliminary sketch by Sneyd for an unused Playboy gag.

  Sneyd’s cartoon roughs have a vibrancy that many cartoonists lack. “Hungry? I also cook in the kitchen.”

  All of the gags on these pages were written by Sneyd’s main collabora
tor, Rex May, as indicated by the initials “RM.” The caption reads “Okay, but nothing kinky.”

  “She’s right, Bernie - She IS a licensed freelance artist’s model.”

  “Oh, I don’t wear a crown - I’m a porn king.”

  “Oh, I’m not worried about that - I’m SURE you’ll respect me in the morning.” Sneyd gathered all his unpublished gag cartoon roughs into a single volume in 2007, called Unpublished.

  DEAN YEAGLE

  One artist inspired by Doug Sneyd was Dean Yeagle, a relative latecomer to Playboy. Unusually, Yeagle had entered the world of erotic cartooning via the more circuitous route of animation. After leaving High School, Yeagle got his first industry job in small studio in Philadelphia, PA. After serving four years in the Navy during the Vietnam War, he returned to animation and worked for former Tom and Jerry animator Jack Zander’s Animation Parlor, in New York. Here, Yeagle honed his craft before setting up his own studio, Caged Beagle, in 1986. It wasn’t until October 2000 that Yeagle first appeared in Playboy, as a winner in the magazine’s Comix and Animation contest with his sexy fantasy warrior illustration, with his first official commission appearing in the May 2001 issue.

  Yeagle’s most popular creation, Mandy (and her pet dog Skoots) was a series of amusing and sexy gag cartoons featuring the fresh-faced, buxom blonde. “An early version of Mandy appeared in a cartoon I did for Playboy,” recalled the artist. “I took that basic look and changed her a bit for a web workshop, gave her the name Mandy, and she suddenly took off as a character in her own right.” In 2003 Yeagle was nominated for Best Gag Award for his Playboy work by the US National Cartoonist Society.

  Mostly working in both color and regular pencils, the cartoonist/animator often scans the original drawing and adds color in Photoshop. Yeagle’s light touch and animation background gives every picture an innate sense of movement, with each drawing looking like a still from an “R” rated animated Disney movie.

  Unsurprisingly, Yeagle was also impressed by great artists like Dink Siegel, Jack Cole, and Harvey Kurtzman and Will Elder who would go on to revolutionize the genre (if not the medium) with their Little Annie Fanny strip, for Playboy…

  Dean Yeagle’s first published Playboy cartoon from 2000. The caption reads, “Oh, it’s stylish battle armor, certainly… but I wonder if it’s really PRACTICAL battle armor…”

  This beautiful color pencil sketch of tree nymphs reveals Yeagle’s twin loves of Disney animation and erotica.

  Yeagle’s popular Mandy character appeared several times in Playboy magazine. This character sketch is one of many he has self-published in his three Scribblings books.

  HARVEY KURTZMAN

  Harvey Kurtzman was once described by the New York Times as “one of the most important figures in postwar America,” and certainly the face of the U.S. comics industry would have been very different without him.

  As a writer, editor, and cartoonist, Kurtzman found his niche at Bill Gaines’ E.C. Comics in 1949, and would later edit the war comics Frontline Combat and Two-Fisted Tales. Kurtzman was known for his painstaking attention to detail, typically sketching full layouts, breakdowns, and even color guides for the stories he assigned to artists—insisting they didn’t deviate from his instructions. Despite, or perhaps because of, his autocratic ways, Kurtzman’s early 1950s work is still considered among the medium’s best.

  Kurtzman was always pushing himself and the medium he loved, so when he realized that E.C.’s other editor, Al Feldstein, was being paid considerably more, he complained to his publisher, who pointed out that Feldstein’s output was greater. During the E.C. Comics witchhunt led by Dr Fredric Wertham in the 50s, the publisher came under attack for Gaines’ horror titles. Inspired by Will Elder’s comic antics, Kurtzman said to Gaines, “We should do something funny. That’s what comic means; funny.” The result was MAD, which changed the face of U.S. comics, influencing nearly every single creator thereafter.

  Kurtzman was headhunted to work on Pageant magazine, but when Gaines agreed to expand MAD from a 10-cent comic book to a 25-cent magazine, Kurtzman stayed with E.C. Although holding onto Kurtzman was Gaines’ main motivation, the revamp also saved MAD from the Comics Code Authority’s censorious overview, assuring its survival to the present. But comics renaissance man Kurtzman only stayed at MAD for a few more issues before ambition got the better of him.

  At the time, Hugh Hefner was picking up MAD and looking for cartoonists for Playboy. Hef was impressed by what Kurtzman had put together and the two struck up a correspondence and an avowed admiration for each other’s work. Hefner later wrote to the artist stating, “I bow to no one in my appreciation for H. Kurtzman.”

  Encouraged by Hefner, Kurtzman demanded a 51% share of MAD magazine, as he had created the entire publication from scratch, along with fellow creators Will Elder, Jack Davis and Wally Wood. Gaines offered 49% but Kurtzman jumped ship, and Hefner was waiting with a lifeboat in the shape of Trump magazine. In 1957, Kurtzman hired his ex-MAD colleagues Elder, Davis, Al Jaffee, and Arnold Roth to work on Hefner’s next big project, Trump—a glossy, upscale magazine version of MAD. Wally Wood was also recruited for the Trump team, but chose to stay at E.C. due to artistic differences that would later become apparent. The magazine’s mascot was a trumpeter in the style of John Tenniel’s Alice in Wonderland illustrations. Hef invested $100,000 in the venture and initial sales were good. Hopes were high for Trump, particularly as it was a new title with a high, 50-cent cover price. But the project was ill-fated. The magazine’s expensive production standards, and the bad timing of its launch, became a financial crunch for Hefner, and Trump was killed after just two issues, long before it could develop a steady readership.

  Will Elder’s breakdown roughs for an unpublished Playboy gag cartoon, with a punter deciding whether to see some Asian hookers, while the blondes discourage him, “Hey John–Buy American!” Elder was Kurtzman’s best friend and main collaborator.

  A 1993 portrait of Harvey Kurtzman drawn by Will Elder for The New Yorker, featuring the former’s many creations such as Goodman Beaver, Hey Look!, MAD’s Alfred E. Neuman and Playboy’s Little Annie Fanny.

  An unused 1960 design rough by Will Elder for a series of spoof sci-fi paperback covers for Girls for the Slime God, an article in Playboy.

  Undaunted, Roth, Jaffee, Kurtzman, Elder, and business manager Harry Chester, set up Humbug as an artist’s collective. But again, despite their best efforts Humbug failed to overcome distribution and financial problems, and folded after 11 issues.

  Never one to give up, Kurtzman and his traveling cartoonists moved to Warren Publishing, where they proceeded to create Help! in 1960. Help! gave the first national exposure to certain artists and writers who would later dominate underground comix, such as Robert Crumb, Gilbert Shelton, Jay Lynch, and Skip Williamson.

  The most notorious strip to appear in Help! was Kurtzman and Will Elder’s 1962 parody Goodman Beaver Goes Playboy! The story showed Archie, Jughead, Betty, Veronica, and all the Riverdale gang engaged in “hep” activities like smoking, drinking, and mass orgies. The whole story was a friendly jibe at Kurtzman’s friend Hefner, who enjoyed it. However, Archie Comics, like Queen Victoria, were not amused. The publisher hit Warren with a lawsuit, and the case was settled out of court, with the creators paying $1,000 each handing over the original art to Archie Comics with the promise that neither of them would ever publish the story again. Bizarrely, the comic duo had parodied Archie in MAD, but no legal action was taken at that time out of professional courtesy between Archie and E.C. Comics. Kurtzman felt angry that his publisher, Jim Warren, rolled over without a fight, as satire is one of the few defenses of copyright use, and is enshrined in the Constitution. The experience left a bitter taste in Kurtzman’s mouth and he began to pack his bags once more.

  A detail from Will Elder’s sketch for The Sunshine Boys movie poster with a nurse who looks uncannily like his and Harvey Kurtzman’s Little Annie Fanny creation.

  Goodman Goes
Playboy: “Oh, come on Arch, you kidder… you make it sound like you’re having an orgy in there.” This classic parody of both Archie Comics and Playboy magazine first appeared in Help! in February 1962. However, it has never been reprinted in its entirety since, thanks to Archie Comics’ humorless and litigious nature. But Playboy publisher Hugh Hefner saw the funny side. Note the amount of detail and individual sight gags Elder manages to pack into this satirical piece, often unscripted by Kurtzman.

  WILL ELDER

  William, Bill, or Will Elder was born in 1921, the same year as Playboy artist Eldon Dedini—and while the two cartoonists were born on opposite coasts of America, their destinies would later converge in Chicago at Playboy.

  During World War II, Elder served in the 668th Topographical Engineers and helped map the coast of Normandy, allowing the D-Day landings to take place.

  Elder’s old buddy Harvey Kurtzman was the driving force behind the duo’s prodigious output and the two worked together throughout their lives. In the late 1940s, they teamed up with Charles Stern to form the Charles William Harvey Studio, creating comics for Prize Comics and other publishers between 1948 and 1951. At E.C. Comics, Elder inked John Severin’s pencils on stories for Weird Fantasy, Two-Fisted Tales, and Frontline Combat, among others, and when Kurtzman created MAD in 1952, he based much of it on Elder’s antics from their high school days.

  Whatever humorous slant Kurtzman devised in his layouts received an amplified comedy boost when Elder drew the finished art, and Elder’s insertion of background gags set the tone for all their collaborative work.