Jay-Z - Never denying his past as a drug dealer and hustler in NYC, Jay-Z has been known for several run-ins with the law. In 1999, he got into an argument with record executive Lance Riviera at a nightclub. Jay believed that Riviera bootlegged his Vol. 3 album and stuck a five-inch blade into Riviera’s abdomen. The rapper said he, “blacked out” with rage during the incident.

Laura Bush - The former First Lady ran a stop sign and killed a friend of hers, Michael Dutton Douglas, who was driving on the other side of the intersection. This took place in 1963, and was not discussed publicly until Mrs. Bush’s autobiography in which she stated, “It was a very tragic accident that deeply affected the families and was very painful for all involved, including the community at large.”

Woody Harrelson - Was arrested in 1982 while dancing in the streets like a madman, the only problem was that he resisted the officers, which increased his sentenced. He was arrested again in 1996 for growing hemp plants in his home.

Danny Trejo - The latino actor spent a healthy amount of time in prison during his 20s. Fueled by a drug addiction, Trejo was in jail for armed robbery, possession, burglary, and assault. His last stint was in San Quentin lasting five years, in which time he became sober and started to turn his life around.

Don King - The famous boxing promoter has been accused and tried for murder not once but twice. He first killed a man by shooting him in the back as the victim tried to rob one of King’s gambling houses he ran as a young man. In 1966, he stomped to death a man that owed him $600. He was convicted of second-degree manslaughter and only served four years in jail.

Jeffrey Jones - Jones who is most well known as the principal in Ferris Bueller’s Day Off and the father in Beetlejuice is a registered sex offender. In 2003, Jones was found in possession of child pornography. He discovered as a pedophile after trying to get a young boy to pose for pornographic photos. He has been arrested twice since the incident, failing to update his sex-offender status in Florida and California.

Marilyn Manson - Manson has been brought to court twice for sexually assaulting security guards during his contest. In 2002, a security guard in Detroit brought Manson to court for the incident, looking for $70,000 in damages claiming emotional stress. The guard claimed that Manson spit on the back of his head and then rubbed his g-string clad crotch on his face and shoulders.

Mark Wahlberg - When Wahlberg was 14 he was sued by the Massachusetts Attorney General in a 1986 hates crimes case. He was accused, along with his two friends Michael Guilfoyle and Derek Furkart, of throwing rocks at black school children. The group pelted them with rocks and yelled racist slurs saying that they didn’t want them in their neighborhood and to get away.

Randy Quaid - Just like his character in The Vacation movies, Quaid turned out to be just as crazy. Quaid has had multiple run-ins with the law, even seeking refuge in Canada to avoid U.S. law enforcement. The main problem he had was owing money to people, most notably an inn located in Santa Barbara, CA. Quaid and his wife skipped out on a bill of $10,000 dollars. He was arrested in Texas for the inn incident, being held on fraud, burglary and conspiracy.

Tim Allen - The lovable Home Improvement star wasn’t always so innocent. In 1979 he was arrested and sent to trial for selling cocaine, having over a pound in his possession, which if found guilty would give him a life sentence. He cooperated with authorities and informed them of other dealers, which let him serve only two years in prison, from 1979 - 1981.