Talk about staying power. At 85, the world’s most legendary bachelor is about to tie the knot for the third time to December 2009 Playmate of the Month, Crystal Harris. In honor of Hef’s Bday and his commitment to Crystal (and his obvious commitment to Viagra), we’ve rounded up the hottest pictures of all his known girlfriends. And while we’re sure Hugh’s had many more girlfriends in his 85 years, we’re absolutely convinced that these 17 are the sexiest.

Hugh Hefner, the man who inspired thousands of women across the country to get Playboy bunny tramp stamps, announced via Twitter on Christmas Day that he’s officially engaged to his one true love, Crystal Harris. In honor of his commitment to Crystal (and his obvious commitment to Viagra), we’ve rounded up the hottest pictures of all his known girlfriends. And while we’re sure Hugh’s had many more girlfriends in his 84 years, we’re absolutely convinced that these 17 are the sexiest.

Hugh Hefner, the man who inspired thousands of women across the country to get Playboy bunny tramp stamps, has announced that he’s ready to settle down with his one true love, Crystal Harris. In honor of his commitment to Crystal (and his obvious commitment to Viagra), we’ve rounded up the hottest pictures of all his known girlfriends. And whil… Click to read more