Say what you want about Hefner, but he was a champion of cartooning. He loved the artform and started out as a cartoonist himself. Playboy ran a lot of cartoons for most of its long run (until recently, in fact) and had many great cartoonist’s work within its pages over the years like Gahan Wilson, Jack Cole, Jules Feiffer, Bobby London, Shel Sliverstein, Dean Yeagle, Eldon Dedini and many others including Harvey Kurtzman and Will Elder. Long before I became a member of the National Cartoonists Society, the Reuben Award Weekend was held in the L.A. area and Hefner hosted a party for members at the Playboy Mansion. In 1963 the NCS gave Hefner the A.C.E. award (Amateur Cartoonist Extraordinaire), an honor given to someone who wanted to be a cartoonist (or tried to be) but ended up becoming a leader in another profession.
Hefner also played a part in the history of MAD Magazine… how big a part depends on who you talk to. As the story goes in 1956 MAD‘s founding editor and main writer Harvey Kurtzman demanded a 51% ownership of the magazine from publisher Bill Gaines. Gaines refused, and Kurtzman left after MAD #28. Shortly thereafter he worked with Hefner on a satircial and more riské version of MAD called Trump. Some say that Hefner met with Kurtzman prior to his making those demands to Gaines and told Kurtzman how much he admired his work, and that if Kurtzman ever left MAD Hefner would find a place for him in the Playboy empire. Others say Hefner tried to steal Kurtzman from MAD by offering him a lot more money and significantly greater resources and budget for whatever he wanted to do. Either way it seems Hefner’s interest in Kurtzman likely emboldened him to make the demands that led to his parting ways with Gaines, and the ushering in of the Al Feldstien era.
Regardless of how if came about, Kurtzman left MAD and started Trump with Hefner. Trump lasted only two issues, primarily because it ended up being very costly to publish (Kurtzman had reportedly racked up over $100,000 in production costs… in 1957!) and Hefner’s publishing empire happened to experience a financial crunch right at that time, forcing Hefner to scale back his non-Playboy endeavors. Hefner was famously quoted at the time: “I gave Harvey Kurtzman an unlimited budget, and he exceeded it.
In 1962 Hefner had Kurtzman and Elder do a cartoon called Little Annie Fanny in Playboy, which ran for 26 years.
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