Model(s):Anna Sophia Berglund, Barbi Benton, Brande Nicole Roderick, Bridget Marquardt, Christa Speck, Crystal Hefner, Donna Michelle, Holly Madison, Hope Olson, Janet Pilgrim, Joyce Nizzari, Karen Christy, Kendra Wilkinson, Kimberley Conrad, Lillian Müller, Patti McGuire, Shannon Lee Tweed, Shera Bechard, Sondra Theodore, Tina Marie Jordan
Uploaded: November 5, 2012
Description: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.