63. Hugh Grant

By the mid-1990s, Hugh Grant had weaseled his way into our hearts, thanks to his bumbling courtship of Andie MacDowell in Four Weddings and a Funeral. Throw bombshell girlfriend Liz Hurley into the mix, and Hugh had it all. Imagine the shock when he stopped stammering long enough to be arrested in the company of Hollywood sex worker Divine Brown in June 1995. She was polishing Mr. Grant’s knob at the time. Overnight, he went from Hugh Star to Lewd Grant–but his Oxford education didn’t go to waste.

Grant went on Jay Leno to tell all. “I think you know in life what’s a good thing to do and what’s a bad thing, and I did a bad thing,” he said. “And there you have it.” Hugh also served up mea-culpa on Larry King. “I don’t have excuses,” he shrugged. The PR offensive worked. Fans held up billboards reading, “I would have paid you, Hugh.”

Still reeling from the incident, Grant and Hurley split up five years later. Grant’s career hasn’t been the same since, and he still cries himself to sleep thinking about films like About a Boy, Love Actually, and Bridget Jones’s Diary.

Watch Hugh Grant sing:

[Charles Bottomley]