Hef's Girlfriends

Of all the leading ladies' men - Romeo, Lothario, Casanova or Don Juan, to name a few - no one has fared better than our founder and editor-in-chief, Hugh Hefner. A famed philanderer, 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 current girlfriend Crystal Harris, we're covering over half a century of Playboy history, and it's only too happy to repeat itself. Throw it back with Hef and his bevy of beauties, right here on Playboy Plus.