Holly
Madison

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.