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'Playboy' Hugh Hefner's hottest girlfriends

April 9, 2012, 5:15 pm
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Publisher, founder and chief creative officer of Playboy Enterprises, Hugh Hefner turns a year older on April 9.
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 1926 born, Hugh Hefner is famous for his colourful personal life. Have a look at his sexiest girlfriends so far. (Reuters Photo)
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Playboy models and twin sisters Kristina and Karissa Shannon. (Reuters Photo)
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Karissa Shannon and Kristina Shannon on a Playboy magazine cover.
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Kimberley Conrad was chosen as Playboy's Playmate of the Month in January, 1988.
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • She gor married to Hugh Hefner in July 1989.
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Conrad and Hefner parted ways after being together for nine years.
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Barbi Benton featured on the Playboy magazine cover many times.
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • It was a dream come true for Barbi Benton (L) when Hugh asked her to be his real life girlfriend. (Reuters Photo)
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Bridget Marquardt is an American television personality, model, and actress. (Reuters Photo)
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Bridget Marquardt dated Hugh for a long time.
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Brande Roderick dated Hugh in early 2000s.
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Kendra Wilkinson is a glamour model and television personality now. (Reuters Photo)
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Kendra Wilkinson is best known for her affair with Hefner.
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Holly Madison and Hefner were together for many years.
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Holly Madison wanted to marry him and have kids, but that was not Hefner's priority. (Reuters Photo)
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Crystal Harris got engaged to Hugh Hefner in December 2010.
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Harris broke off the engagement on June 14, 2011, five days before their planned wedding. (Reuters Photo)
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Kara Monaco with Hefner at a do. (Reuters Photo)
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Kara Monaco was chosen as Playmate of the Month by Playboy magazine in June, 2005.
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • Playboy magazine founder Hugh Hefner poses with his six girlfriends (L-R) Sheila Levell, Izabella St James, Zoe Gregory, Holly Madison, Bridget Marquardt and Cristal Camden, pose for the cameras. (September 20, 2003) (Reuters Photo)
    Reuters
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends
  • 'Playboy' Hugh Hefner's hottest girlfriends