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Playboy

Special Edition

Holly
Madison

Holly Madison 12 photos
Birthplace:
Astoria, Oregon
H:
5' 4"
W:
118 lbs
36D-23-36
Of all the leading ladies’ men – Romeo, Lothario, Casanova, Don Juan – no one has fared better than our founder and editor-in-chief, Hugh Hefner. A famed philanderer, not to mention philanthropist and armchair philosopher, Hef has enjoyed the privilege of the company of some of the most beautiful women in the world – more often than not from the comfort of his own home, which just so happens to be the Playboy Mansion. In this pictorial, we take a long look back at Hef’s best-loved girlfriends – from spread sheets with Playboy secretary Janet Pilgrim to the two-step with Barbi Benton and Karen Christy; a lead role with Shannon Tweed to marriage and children with Kimberly Conrad; turns with the Bentley twins to turns with the Girls Next Door, all the way to the new Mrs. Hefner, Crystal Harris – and in the process, over half a century of Playboy history.
  • November 5, 2012
  • comments


17 comments

  • Anonymous
    Anonymous
    "Who is the girl in picture #30?" - Anna Sophia Berglund
  • badbreaker
    badbreaker
    Hef , you are the best !
  • Anonymous
    Anonymous
    Go Hef Go!!!!!!!!!!!!!!
  • Anonymous
    Anonymous
    Who is the girl in picture #30?
  • Anonymous
    Anonymous
    Why no Terri Welles?
  • Anonymous
    Anonymous
    I didn't know some of these girls had been with Hef.
  • Anonymous
    Anonymous
    who is the girl in picture #31 ?
  • Anonymous
    Anonymous
    Who is the girl in picture #5?
  • Anonymous
    Anonymous
    Who is the girl in picture #5? = Donna Michelle. also seen in #20
  • Anonymous
    Anonymous
    "why no Stephanie Heinrich?" = she isn't well-known like the others. she does appear in photo #24, below anka romensky and kissing hef
  • Anonymous
    Anonymous
    Hef you "cherry picked" the hottest women
  • Anonymous
    Anonymous
    why no Stephanie Heinrich?
  • Anonymous
    Anonymous
    "who is the girl in picture #31 ?" = Shera Bechard
  • PETER
    PETER
    Who is the girl in the red bikini top and blue bottoms with long blonde hair ? She is standing beside Hef who is wearing a red robe and hat .
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