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.
