23/07/2013 09:15 | By Sam Ashton, contributor, MSN Him
The famous men punching above their weight

Hugh Hefner and Crystal Harris



Hugh Hefner and Crystal Harris (© Russ Elliot/AdMedia/SIPA/Rex Fea)
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It may seem like an obvious one, but Hugh Hefner is surely the king of punching above his weight. The 87-year-old Playboy founder has been romantically involved with a number of his Playboy playmates, but decided to marry 27-year-old Crystal Harris in 2012 after she had spent some time as his 'number one girlfriend'.

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