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.

For many college students, grads, and young professionals, a career path can be a cloudy one – a mixture of doubt and confusion, purpose and experimentation. For Mr. Hefner, it was a journey many others could sympathize with but no one has duplicated. He served as a writer for a military newspaper in the U.S. Army. He graduated from the University of Illinois at Urbana-Champaign, worked as a copywriter for Esquire then raised $8,000 from 45 investors to launch Playboy. The rest is history. We’ve collected almost 40 photos of Hef during these formative years. Prepare to stare into the face of determination after the jump!

We learned three things looking through hundreds of Crystal Harris’ TwitPics over the weekend: One, she’s crazy about the Little Mermaid. Two, she loves her dog Charlie. And three, Crystal looks hot doing ANYTHING! The future Mrs. Hugh Hefner is so hot she makes drinking coffee look like a scene from a Cinemax After-Dark feature. But don’t take our word for it. These 108 TwitPics of December 2009 Playboy Playmate Crystal Harris speak for themselves.

As we announced earlier, Hugh Hefner got engaged to his girlfriend, December 2009 Playboy Playmate of the Month, Crystal Harris on Christmas Eve . According the the 84 year-old envy of all men via Twitter, when he gave “the ring to Crystal, she burst into tears” making it “the happiest Christmas weekend in memory”.
We know a great… Click to read more

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.

The Shannon Twins might be bigger fans of Playboy than us, and they might have just scored themselves a bedroom in the mansion. See, not too long ago, it was starting to look like Hugh Hefner’s Playboy days were going down the tubes. First came the reports of Playboy’s speculated bankruptcy – which, after all the bullsh*t that’s bee… Click to read more