34. Vanessa Williams
Most Infamous Moment: Old nude photos of Williams, then Miss America 1984, surfaced and were published in Penthouse, forcing her to give up her title.
Before Williams became the big TV star we know her as today (with Ugly Betty and Desperate Housewives under her belt), she was embroiled in a nude photo scandal. Photos she had taken two years prior for photographer Tom Chiapel, for whom she worked as an assistant at the time, found its way to the pages of a major publication, which caused her to resign from her position. The $500 million lawsuit she filed against Chiapel and Bob Guccione, the publisher of Penthouse, was eventually dropped a year later.