Sex, sure—but what does Hugh Hefner have to do with comedy? Quite a lot, actually.
After running the college humor magazine at the University of Illinois (named The Shaft—no comment), Hefner worked at Esquire, at that time the nation’s top market for gag cartoons. Hefner’s love of cartooning and humor writing showed in his own magazine Playboy, which immediately became the main meal ticket for several generations’ worth of creators.  While everybody justifiably celebrates what The New Yorker has meant to American comic writing and cartoons, since hitting newsstands in 1953 Playboy has done as much or more. From Jean Shepherd to Harold Ramis to Gahan Wilson, Playboy has played a pivotal role in countless comedy careers.
In 1957, Hefner attempted to start a national humor magazine called Trump, hiring Harvey Kurtzman, Will Elder and others away from MAD. In many respects National Lampoon 15 years early, the first issue of Trump sold out—almost unheard of in the magazine business. Unfortunately, pressure from other parts of the Playboy empire forced Hefner to shutter Trump after just two issues. (I got the full story of Trump from my friend Arnold Roth, who was a contributor, as well as a confidant of Kurtzman’s.)
Hefner was also a patron of standup, passing legions of comics through his Playboy Clubs. Always desegregated in a time when many nightclubs weren’t, these were especially important in breaking black comics like Dick Gregory, Godfrey Cambridge, and Bill Cosby. And Hefner’s TV shows, most notably “Playboy After Dark,” introduced tons of comedians to a national audience. Hefner even paid Lenny Bruce to write his autobiography, How to Talk Dirty and Influence People, ghosted by The Realist‘s Paul Krassner.
From the mid-50s to the early 70s, nobody did more to support and extend American comedy than Hugh Hefner. Hefner realized, correctly, that the sexual freedom his magazine promulgated also expressed itself in satire—comedy was a definite part of the Playboy philosophy. Though subsequent decades would show the limits of that vision—in both sex and comedy—Hefner remains a vitally important, tremendously influential person in the history of American humor. —Michael Gerber
Hefner on his friendship with Lenny Bruce
Trailer of documentary “Hugh Hefner: Playboy, Activist, and Rebel”
Lenny Bruce on “Playboy Penthouse” (Oct 1959): Part 1 • Part 2 • Part 3
A bit more on Dick Gregory which mentions his Playboy Club experience
…much more to come!
