Large age gaps in couples are always fodder for speculation. But to stand out in Tinseltown, the difference has to be extreme. Anna Nicole Smith started the trend by marrying 89-year-old billionaire J. Howard Marshall when she was just 26. A decade later, Holly Madison, Bridget Marquardt and Kendra Wilkinson perfected the art by simultaneously dating Hugh Hefner while filming The Girls Next Door. Their bizarre four-way relationship intrigued audiences and made them demi-celebrities in their own right. The girls may be done with their Playboy reality show, but each has landed her own solo gig: Planet Holly, Kendraand Bridget's Sexiest Beaches.