19. Flavor Flav
The Public Enemy member has been arrested on a few occasions with this mug shot stemming from an arrest in Las Vegas after police pulled him over at 12:30 in the morning on suspicion of driving under the influence and having an open container of alcohol in his 2005 black BMW.
18. Chris Tucker
Comedian and actor Chris Tucker got arrested and briefly jailed in 2005 when he was pulled over in Georgia for driving 109 miles per hour (well over the speed limit) in his 2005 Bentley. In addition, Tucker did not immediately stop for the police officers. He only spent about 30 minutes behind bars before getting released.
17. Charlie Sheen
One of the hardest things about Charlie Sheen’s mug shots is that it is getting increasingly more difficult to match each photo to its specific offense. Sheen has been in legal trouble for drug abuse and domestic violence since 1990. His most recent arrest was in 2009 when he was arrested in Colorado and booked on suspicion of second-degree assault.
16. Shia LaBeouf
Before Shia LaBeouf had some artistic realization that led him to create over-the-top pieces of performance art in front of the awaiting cameras of the paparazzi, he was creating public outbursts to gain the attention of the media. This specific shot was taken after LaBeouf was arrested for causing a disturbance during the Broadway show Cabaret in 2014.
15. Tim Allen
Tim Allen became a comedic powerhouse when he played Tim “The Toolman” Taylor on the smash hit Home Improvement. When he was only a 25-year-old with an incredible mustache, he was detained at an airport in Michigan for possessing an incredible amount of cocaine. He was facing life in prison when he made a deal with authorities that gave them the names of 21 people involved in the trafficking ring.