Few men of the 20th century were more powerful in the worlds of magazine publishing or pornography as Larry Flynt, the controversy-courting magnate who founded Hustler in the 1970s and turned the brand into an empire of clubs, casino, film companies and more. After nearly 50 years in the adult film business, Flynt has died. He was 78 years old. According to TMZ, “the mogul passed Wednesday morning in Los Angeles from heart failure.”

Born in Kentucky, Flynt served in the Army and Navy before he opened his first bar featuring nude waitresses and go-go dancers. He called it the Hustlers Club. By the early 1970s, the club business was booming and Flynt started the Hustler Newsletter to promote it. When his clubs later struggled, Flynt refocused his energies on Hustler, turning it into a full-fledged magazine and taking it nationwide. The magazine, which was far more explicit than Playboy, became a hit.

The magazine was so graphic, in fact, that Flynt was in constant legal trouble over its content. During one case in Georgia, Flynt was shot while entering the courtroom; the subsequent damage to his spinal cord left Flynt partially paralyzed for life.

His battles over Hustler, along with his health issues and struggles with addiction were later dramatized in the Hollywood film The People vs. Larry Flynt. Woody Harrelson played Flynt on his rise from club owner to porn icon, and depicted his legal battles, which eventually went all the way to the Supreme Court.

Larry Karaszewski, who co-wrote The People vs. Larry Flynt screenplay with Scott Alexander, wrote a tribute to his former subject on Twitter. “Hate him, love him - Larry Flynt was one of a kind.” And so he was.

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