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Hefner is pictured above in holding up his first magazine cover. Views Read View source View history. He spent much of his time writing and drawing cartoons, and in middle school began reading Esquire, a magazine of sex and substance Hefner wanted Playboy to emulate. Sammy Davis Jr. He is pictured on the Playboy jet in the 70s.

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But as time wore on Playboy began to face stiffer competition, first from softcore pornography magazines such as Penthouse inthen later from harder fare such as Larry Flynt's Hustler, which debuted in We Do! News since E! Sign Up. Fashion Critical. He was

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