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With his Playboy Enterprises Inc in talks to be sold for about $300 million, the 83 year-old Hefner will be giving up control over the iconic adult entertainment empire he founded that was instrumental in shaping society's opinions on nudity, sex and free speech.
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"Hef" turned Playboy and its bunny head logo into a symbol for a lifestyle he embodied as bachelor extraordinaire, living in a mansion surrounded by wealth and beautiful women.
"This guy was one of the major players in the transformation of American culture in the second half of the 20th century and not just because he had a magazine with naked women in it," said Robert Thompson, a professor of pop culture at Syracuse University.
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But even as it grew ever more popular, the magazine created rivals such as Penthouse and Hustler. In the 1980s, adult videos grew into a major business and by the late 1990s, the rise of the Internet and free pornography on the Web became Playboy's greatest rival for an audience.
REALITY STAR
Hefner remains in the limelight today, showing up at media events with numerous girlfriends by his side. He enjoyed a role in reality television show "The Girls Next Door" on cable network E! and his dating life and break-up with model Holly Madison made him a staple of celebrity magazines.
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He has described himself as having liberated America from its Puritan past and experts agree he did make sexual images and content more acceptable to Americans.
But Playboy magazine also showed men how to enjoy stylish clothing, good liquor, sports cars and other luxuries, and became a standard bearer for that lifestyle -- real or imagined.
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But as Playboy's fortunes waned, some of the symbols of wealth that surrounded Hefner became harder for him to hang on to.
In the early 1980s, he had to give up a private jet plane with a bedroom, a miniature disco and a kitchen, Watts said.
Through the decades and despite the loss of business, Hefner continued to live the good life and made sure everyone knew it.
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Source: Reuters