We know Hugh Hefner’s playboy (no pun intended) days are pretty much over, but over the years the man known as Hugh Hefner has conquered some of Playboys most notable women.

During his 60s and 70s (and even early 80s) he’s had his fair share of playmates and at times the Playboy mag founder would date several at a time. His first wife might be the only woman in his life that got all his time but that was before Playboy became the giant that it is now. During the last 30 years Hef only dated Playmates and most of them being blondes.

The Bentley Twins

During his early 70s — that’s right his 70s — Hugh was known to have as many as seven girlfriends at a time.  And during that time The Bentley twins Mandy and Sandy were apart of the entourage of ladies Hef rolled with during the late 90s and early 2000s. Hef was doing his thing back then.