Knee-to-Knee with Hefner: An Interview with the Oldest Playboy

Sex forges unlikely alliances and Hugh Hefner, who has been the world’s most prominent personification of the unchained heterosexual male libido since his 1953 launch of Playboy magazine, forges unlikelier alliances than most. It’s not only that the 85-year-old is looking forward to marriage later this month to Crystal Harris, a psychology major-turned-Playboy Playmate and aspiring pop singer 60 years his junior.

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Marge Simpson graces Playboy cover

If those coveted 20-something readers can’t identify with Hugh Hefner, maybe they will with “The Simpsons.” Like nearly everything printed on paper these days, Playboy magazine has been facing tough times. Advertising pages have dropped 31 percent over the last year, newsstand sales have dried up by 25 percent, and its circulation has dipped to 2.4 million, according to publishing insider Media Industry Newsletter.

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