But it seems the pair were meant for each other, as on New Year’s Eve 2012, Crystal, 26, and Hugh, 86, tied the knot.

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In 1989, Hugh married Playmate of the Year Kimberely Conrad, who was 36 years younger than her husband.

The couple had two children, Marston and Cooper, but they split in 1998.

READ MORE Barbi Benton -- Hugh Hefner's former girlfriend known for discovering the Playboy Mansion in the '70s -- thinks the famous home should stay that way.

The Playboy founder has died at the age of 91, passing away peacefully at the Playboy mansion surrounded by his family.

He has been married to Crystal Hefner since December 31, 2012.

He was previously married to Kimberley Conrad and Mildred Williams.in 2006, "but because she believed in her son."), to launch Playboy, which was initially going to be called Stag Party.The first issue, published in December 1953, featured Marilyn Monroe from her 1949 nude calendar shoot and sold over 50,000 copies.) After the Charles Beaumont science fiction short story "The Crooked Man" was rejected by Esquire magazine in 1955, Hefner agreed to publish the story in Playboy.READ MORE Hugh Hefner went to his final resting place Saturday, but only a select few of his closest friends and family were on hand for the ceremony ... and the most famous Hef impersonator plans to do his part to keep Hef's legacy alive.George Kane's been making a living for years as a "dead…In January 1952, Hefner left his job as a copywriter for Esquire after he was denied a raise.