Of all the leading ladies' men – Romeo, Lothario, Casanova, Don Juan –
no one has fared better than Playboy 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 current girlfriend Crystal Harris – and in the
process, over half a century of Playboy history. See all of Hef's
girlfriends nude at the Playboy Cyberclub. See the hottest Playmates only at
Playboy