Proving that possessing a mischievous grin and a hellraiser past is way more of a babe magnet than some pretty boy jaw line and feathered hair, Jack the Man has been the finest purveyor of XX chromosomes since waaaay back when. The rubber-faced icon has had flings with a plethora of hotties, including Playboy cover star Bebe Buell, Mamas & the Papas sexpot Michelle Phillips, and the vastly underrated Anjelica Huston, all the while rocking a receding hairline, gradually porking out, and wrinkling like a champion. Word.
