If Hugh Hefner was the Caesar of magazine sex, Bob Guccione was surely its Caligula. Like Penthouse, the magazine he founded in 1965, Guccione radiated a sleazy, erotic charisma. By the 1980s, he had a $300 million publishing empire and a $150 million art collection, built largely on his counter-strategy to Hef's sanitized image of American womanhood: Guccione restored the sin to skin.
But while Penthouse sold millions and made headlines with early nude photos of Madonna and then Miss America Vanessa Williams, the rest of his empire was crumbling: start-up magazines like Omni and Viva shuttered, and abortive plans for a Penthouse casino in Atlantic City cost him $160 million. And then there was his late-'70s film farrago, Caligula at $17.5 million, the most expensive porno ever made which despite its Gore Vidal script and pedigreed cast prompted Roger Ebert to call it "sickening, utterly worthless, shameful trash."
A more systemic calamity lurked in the '80s: the rise of home video. Smutty pictures that moved had an immediacy that Guccione's artful erotic tableaux lacked. Much of his later life was consumed in lawsuits, bankruptcy hearings and the selling off of his art collection (Penthouse was eventually bought by a private equity investor in 2004). The porn Caligula's empire declined and fell, and with it ended the reign of one of the publishing world's two monarchs of flesh.
A version of this story previously appeared on TIME.com on Oct. 21, 2010.