13. Robert Downey Jr.
While he plays a superhero on the big screen, Downey was known as quite the player when he was younger. With a rap sheet that includes drug possession, drunk car racing, breaking parole, and trespassing (entering a neighbor’s house and passing out on their bed), the now-Iron Man once spent time earning 8 cents an hour scrubbing pans in the Los Angeles County Jail for 18 months. Going from that to being the one of the highest paid actors in Hollywood has been quite a feat!
14. Paris Hilton
It is about time we see some women on this list too! Paris Hilton, great grand-daughter of the Hilton Hotel mogul, is just too wealthy for her own good. Her modeling and reality television career led her into the LA party scene and eventually ended up being arrested in 2006 for DUI. After several other driving infractions, Hilton was in violation of probation and was sentenced to 45 days in jail. She served about half of her time and spent part of it in the medical wing of the facility.
15. Phil Spector
Originally known for being a musician and record producer, Phillip Spector was quite famous in the 1960’s. His career declined but he made the news again in 2003 when he was convicted of killing actress Lana Clarkson, which Spector tried to play off as a suicide. As it turns out, he had pulled a gun on at least four other women, but this time he actually killed her. Spector was sentenced to 19 years in prison and will be 88 years old before he is eligible for parole.
