Before he was brushing elbows with Barack Obama in the White House, Jay-Z had a checkered past. Jay-Z was arrested for the 1999 murder of his rap colleague Lamont “Big L” Coleman, and was facing up to 40 years in prison. The two were very close and collaborated on a few projects.
23. Hugh Grant
Hugh Grant’s name became synonymous with mugshots in the 1990s. This awkward photo was snapped after he was arrested in Los Angeles for soliciting sex from a prostitute. The actor had just earned himself industry praise and respect for his film Four Weddings and a Funeral and immediately fell onto the Hollywood blacklist.
22. Vince Vaughn
Vaughn was arrested alongside Steve Buscemi and screenwriter Scott Rosenberg in 2013 while they were filming Domestic Disturbance. Ironic, right?
The group was drinking at a bar in North Carolina when a local man picked a fight with the actor for talking to his girlfriend, and Buscemi wound up getting stabbed during the incident.
21. James Brown
James Brown might be the king of soul, but he has definitely had a lengthy career behind bars. One of his run-ins with the law happened on September 24, 1988, when he entered an insurance seminar in Augusta, Georgia armed with a shotgun and pistol. He was chased across state lines into South Carolina where he was arrested.
20. Anna Nicole Smith
Anna Nicole Smith was arrested while she was living in Houston, Texas after she was pulled over for driving under the influence. Since she was not quite famous at the time, the incident did not receive much attention. When she was released, she returned to her job waiting tables at Red Lobster.