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  • Published
    20 Images

    The Handsome and Always Charming Hugh Hefner

    Playboy's founder shows no signs of slowing!

  • Hef, Karissa and Kristina Shannon and Crystal Harris
    April 4: Hef (left center) with twin ex-girlfriends Karissa and Kristina Shannon, and his fiancee, Crystal Harris (far left).
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    Denise Truscello
  • Hugh Hefner and Holly Madison
    April 4: Hugh Hefner and ex-girlfriend Holly Madison reunited for his 83rd birthday.
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    Denise Truscello
  • Kendra Wilkinson and Hank Baskett
    April 4: Kendra Wilkinson and Hank Baskett party at Hef's 83rd birthday celebration.
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    Denise Truscello
  • Bridget Marquardt and Hef
    April 4: Bridget Marquardt serenades Hef with a 'Happy Birthday' tribute.
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    Denise Truscello
  • Hef and the girls
    April 4: Hef parties with his girls through the years. From l to r, the Shannon twins, Kendra Wilkinson, Bridget Marquardt, Hef, Holly Madison and Crystal Harris.
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    Denise Truscello
  • Hugh Hefner, Karissa and Kristina Shannon
    Hugh Hefner debuts his new twin girlfriends, Karissa and Kristina Shannon.
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    E! Online
  • Hugh Hefner, Karissa and Kristina Shannon
    Hugh Hefner's holiday card featuring Karissa and Kristina Shannon.
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  • Hugh Hefner and his girlfriends
    Feb. 25: Hugh Hefner, founder and Chief Creative Officer of Playboy Enterprises, arrives with his girlfriends at the "Festival di Sanremo" Italian song contest, in San Remo, Italy.
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  • Hugh Hefner and his girlfriends
    Feb. 20: Hugh Hefner, founder and Chief Creative Officer of Playboy Enterprises, talks during the "Festival di Sanremo" Italian song contest, in San Remo, Italy.
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  • Quincy Jones and Hugh Hefner
    Feb. 25: This photo released by the Playboy Jazz Festival shows music producer Quincy Jones, left, with Playboy founder Hugh Hefner during a news conference at the Playboy Mansion in Los Angeles.
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  • Hugh Hefner
    Hugh Hefner, the founder of Playboy, seen in an April 7, 2006 photo.
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  • Holly Madison and Hugh Hefner
    Sept. 24, 2008: Holly Madison, left, and Hugh Hefner arrive at the Fox Reality Channel Really Awards in Los Angeles.
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  • Holly Madison, Hugh Hefner, Bridget Marquardt, and Kendra Wilkinson
    June 7, 2007: Holly Madison, Hugh Hefner, Bridget Marquardt, and Kendra Wilkinson.
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  • Hugh Hefner and Pam Anderson
    Dec. 4, 2003: Hugh Hefner, the founder of Playboy magazine, and Pam Anderson celebrate the 50th anniversary of Playboy magazine in New York.
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  • Hugh Hefner and Kimberly Conrad
    Aug. 8, 1995: Hugh Hefner and wife Kimberly Conrad.
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  • Hugh Hefner
    Nov. 11, 1982: Playboy founder Hugh Hefner shown with a Playboy magazine and a Playboy video.
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  • Hugh Hefner and Barbi Benton
    April 2, 1974: Playboy founder Hugh Hefner shown arriving at the 1973 annual Academy Awards in Hollywood with actress Barbi Benton.
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  • Hugh Hefner and Bonnie J. Halpin
    June 20, 1961: Hugh Hefner poses with 'bunny-girl' hostess Bonnie J. Halpin at the Playboy Club in Chicago.
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  • Hugh Hefner and Barbi Benton
    Sept. 5, 1969: Hugh Hefner, publisher and owner of Playboy, and his girlfriend Barbara Benton, a 19-year-old coed turned actress, are surrounded by Bunny Girls at the Playboy Club in London.
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  • Christie Hefner
    Dec. 1, 2005: Christie Hefner, the CEO and chairwoman of Playboy Enterprises.
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  • Published
    20 Images

    The Handsome and Always Charming Hugh Hefner

    Playboy's founder shows no signs of slowing!

Move Forward
  • The Handsome and Always Charming Hugh Hefner
  • Hef, Karissa and Kristina Shannon and Crystal Harris
  • Hugh Hefner and Holly Madison
  • Kendra Wilkinson and Hank Baskett
  • Bridget Marquardt and Hef
  • Hef and the girls
  • Hugh Hefner, Karissa and Kristina Shannon
  • Hugh Hefner, Karissa and Kristina Shannon
  • Hugh Hefner and his girlfriends
  • Hugh Hefner and his girlfriends
  • Quincy Jones and Hugh Hefner
  • Hugh Hefner
  • Holly Madison and Hugh Hefner
  • Holly Madison, Hugh Hefner, Bridget Marquardt, and Kendra Wilkinson
  • Hugh Hefner and Pam Anderson
  • Hugh Hefner and Kimberly Conrad
  • Hugh Hefner
  • Hugh Hefner and Barbi Benton
  • Hugh Hefner and Bonnie J. Halpin
  • Hugh Hefner and Barbi Benton
  • Christie Hefner