Hugh Hefner and Crystal Harris Tie the Knot: The Many Loves of the Ultimate Playboy

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Hugh Hefner and Crystal Harris Tie the Knot: The Many Loves of the Ultimate Playboy
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Hugh Hefner Weds Crystal Harris

Hugh Hefner is off the market!

The perennial playboy has finally made an honest woman out of his runaway bride, Crystal Harris. The Playboy magazine founder and his beautiful bride tied the knot in a New Year's Eve ceremony at the iconic Playboy Mansion in Los Angeles.

The couple have been engaged since December 2010. They were originally scheduled to get married back in June 2011 until the bride got cold feet a few days before the big event. This is the third marriage for Hefner, 86, and the first for his much younger bride, 26.

"When the wedding didn't work out the first time, it was because of me," Harris told US Weekly. "I needed to explore out there and take the time away [from Hef and the Mansion]. The time away really helped make me realize that where I'm meant to be is here with Hef. Our relationship is better than it ever has been before. I'm very happy and Hef's very happy and we're excited."

Here are few of the ladies who tried to tame the eternal bachelor:

Mildred Williams: Long before he became the iconic playboy, he married his college sweetheart in 1949. The couple would go on to have two children, Christie Hefner who now helms her dad's publishing empire, and son David. She stood by his side as he left his copy writing job at Esquire magazine to launch Playboy in 1953. They divorced in 1959.

Barbi Benton: The beautiful brunette held Hef's attention throughout the much of the 1970s. While she was still in her teens, she took up the role as co-host to Hefner on the television show, "Playboy After Dark." After appearing together on screen, the couple decided to try out their relationship off-camera when the 42-year-old publishing giant asked the 18-year-old co-ed out on a date. Benton would appear on the cover of Playboy magazine four times between 1969 and 1985 and was able to broaden her career to traditional television shows including "Hee Haw," "The Love Boat" and "Fantasy Island." The couple never married, but have remained friends since they split up in 1976.

Kimberly Conrad: For his second take at marriage, Hef turned to the Playmate family of beauties to find his new bride. After suffering a minor stroke in the mid-80s, he decided to take a walk on the mild side and give married life a second try with Playmate of the Year Kimberly Conrad in 1989. The couple had two children - sons Marston and Cooper. They made it work for almost a decade until his wild side began to roar and she moved into a house next to the famed mansion. The couple divorced in March 2010 following an eleven year separation.

The Girls Next Door: Who could forget the trio of beautiful blondes who put their "relationships" with the playboy on reality TV? Holly Madison, Kendra Wilkinson and Bridget Marquardt jumped on the reality television bandwagon in 2005 with an inside look at Hef and his bevy of beauties inside the Playboy Mansion. For five seasons, viewers watched the ladies various adventures both inside Hef's world and as they branched out on their own. All three ladies ultimately left the mansion and their "boyfriend" for greener pastures in 2009.

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