Hugh Hefner trough the years Photos

  • Playboy Enterprises released a statement on Sept. 27, 2017 that the company founder, Hugh Hefner, passed away at the age of 91. Here, he poses for a portrait in Los Angeles in 2009.

    Jay L. Clendenin/Los Angeles Times/Contour by Getty Images

  • American publisher Hugh Hefner is seen in this 1955 portrait sitting in front of a wall collage of female centerfolds from his men’s magazine ‘Playboy’ which he launched in 1953.

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  • Hugh Hefner, Publisher of Playboy, is shown with Cynthia Maddox, the blond cover girl on the February issue of his magazine, arriving in New York on Jan. 29, 1962. They are visiting to attend a party given by Ella Fitzgerald at the Basin Street East in honor of winners of the Playboys jazz poll.

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  • Playboy editor and tycoon Hugh Hefner is greeted by a group of bunny girls from his Playboy Clubs, upon his arrival at London Airport, June 25, 1966.

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  • The president of Playboy Enterperises, Hugh Hefner with girlfriend, Barbi Benton in his luxury DC-9 aircraft ‘The Big Bunny’ at Heathrow, England, July 29, 1970. The couple are en route to an extended holiday around Europe.

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  • Hugh Hefner, publisher and founder of Playboy magazine, and his girlfriend Barbi Benton are welcomed by ‘Bunny Girls’ from the London Playboy Club, on their arrival at Heathrow Airport aboard his private DC 9 jetliner, July 29, 1970.

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  • Hugh Hefner, Sondra Theodore (right) and guest are seen at the Tennis and Crumpet Tournament on May 21, 1977 in Beverly HIlls, Calif.

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  • Carrie Lee and Hugh Hefner are seen at the premiere of “Beverly Hills Cop II” in Los Angeles on May 19, 1987.

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  • Hugh Hefner, Marsden Hefner and Kimberly Conrad are seen at the Playboy Playmate of the Year celebration on April 25, 1991 in Bel Air, Calif.

    Ron Galella/Getty Images

  • Hugh Hefner, center, celebrates the upcoming May issue of Playboy with his girlfriends, Sandy and Mandy Bentley, April 12, 2000 in New York City.

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  • Hugh Hefner and Playboy Bunnies are seen in this Aug. 23, 1995 photo.

    Steve Granitz/Getty Images

  • In this undated publicity photo released by the E! cable channel, Kendra Wilkinson, Hugh Hefner, Holly Madison and Bridget Marquardt, from left, pose poolside at Hefner’s Beverly Hills, Calif., estate during a birthday party for Wilkinson. “The Girls Next Door,” a reality series about Hefner and the women billed as his girlfriends.

    Elayne Lodge/E!/AP Photo

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