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100 Unsexiest Men 2009

66. HUGH HEFNER

VIAGRASAURUS REX

For more years than he can remember, this pajama-wearing coot has paid his hot-tub bills by getting the girl next door to take off her top. But now, as his Playboy empire is slipping, it seems his harem is also crumbling. Up until recently, the legally married octogenarian still had a trio of highly visible girlfriends, but two of them left him last year. You know times are hard when even Hef has to downsize. 

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