Troubled Celebrities
- Robert Downey Jr has revived his career in the Iron Man franchise where he plays this playboy billionaire. (no points for saying Iron Man). Tony Stark
- Lindsay Logan is trying to turn her career around. She had a chance to in 2009 but passed on the role of “jade” in this blockbuster comedy. The Hangover
- Hugh Grant was arrested in 1995 after Cops caught him with a prostitute. In the days that followed, Grant appeared on this late night talk show where the host asked him “what the hell were you thinking?” (Bonus point for the name of the hooker. Tonight Show with Jay Leno, Divine Brown
- Mike Tyson has been in trouble with the law since he was a kid, but in 1990 he was the heavy weight champ. That is, until he was upset in Tokyo by this boxer in one of the biggest upsets in boxing history. Buster Douglas.
- Lil Kim was sentenced to 1 year in prison in 2006 for perjury. But she won a Grammy award for this song. A collaboration with Christina Aguilera, Pink, and Missy Elliot. Lady Marmalada
- In 2002 Joshua Jackson was arrested for assaulting a security guard at a hockey game. Which is ironic because Jackson might be best known for playing this character in the Mighty Ducks franchise. Charlie Conway
- This Hollywood heiress serves 22 days in jail in 2007 for driving twice with a suspended license. Paris Hilton
- Paul Rubens, better known as this, was arrested in 1991 for indecent exposure at a porno theatre. He was then arrested for child porno in 2002. Pee Wee Herman
- This world famous New Jersey singer was arrested in 1938 for “Seduction and Adultery”. His mugshot can most likely be found at every poster section in a college book store. Frank Sinatra
- This famous skateboarder, best known for his work on MTV, has been arrested for most things that are associated with being a jackals. He lives in West Chester PA. Bam Margera
TIE BREAKER: How many professional fights did Mike Tyson have in his career? 50