8 Celebrities Who Have Been Arrested More Than Anyone Else!

Published on April 1, 2014. Updated April 5, 2017

Celebrities have interesting lives – they can potentially make a lot of money, but everything they do is well publicized, so there can be a lot of scrutiny. This is particularly difficult for stars who attract trouble everywhere they go. For this reason, we’ve decided to find out which celebrities have had the most run-ins with the law! Here is a list of 8 celebrities who have been arrested the most times – click through to see which star has been arrested a whopping 66 times!

8. Michelle Rodriguez

Total Arrests: 5

Michelle Rodriguez – best known for her role as Letty Ortizin in “The Fast and Furious” franchise – has been arrested for assault, hit and run, driving with a suspended license and DUI. In 2008, she spent 18 days of a 180-day jail sentence behind bars for violating her probation in a DUI case.

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7. Lindsay Lohan

Total Arrests: 5

Lindsay Lohan has been having some serious problems with the law since 2007 when she got her first DUI. Her rap sheet also includes a hit and run, assault and possession of cocaine. Even after numerous stints behind bars, this troubled starlet still doesn’t seem like she is any closer to getting her act together.

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6. Sean Penn

Total Arrests: 6

Sean Penn began having problems with the law around the same time that he started dating Madonna back in the ‘80s. In 1987, he was arrested for assaulting a photographer on a film set and was sentenced to 60 days in jail as a result. In 2009, he was charged with battery and vandalism for punching a photographer and breaking his camera.

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5. Robert Downey Jr.

Total Arrests: 6

Robert Downey Jr. is one of the best examples of a troubled star who, after hitting rock bottom, has enjoyed a long and lucrative career. Between 1996 and 2001, he was arrested numerous times on drug related charges including cocaine, heroine and marijuana. After two trips to jail, the “Iron Man” star finally kicked his bad habits and  has been incredibly successful in Hollywood ever since.

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4. T.I.

Total Arrests: 7

T.I. has an impressive rap sheet. Before he was even a teenager, he was already having problems with the law and it’s only worsened over the years. He has been arrested for trying to purchase guns from a federal agent and drug charges. Before he was set to perform at the BET Hip-Hop Awards in 2007, he was arrested for possession of three unregistered machine guns, two silencers and possession of firearms by a convicted felon.

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3. Snoop Dogg/Snoop Lion

Total Arrests: 8

Snoop Dogg (who now goes by the name Snoop Lion) has had problems with the law dating all the way back to 1990 when he was convicted of felony possession of drugs and possession for sale. Since then, most of his arrests have been for marijuana possession. His most recent arrest was in 2012 after he tried to enter Norway with eight grams of marijuana.

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2. DMX

Total Arrests: 13

Since becoming famous, DMX has been arrested 13 times for everything from animal cruelty and reckless driving to unlicensed driving and drug possession. Last year was a particularly bad year for the rapper – he was arrested four times in total for driving with a suspended license, driving under the influence and possession of marijuana.

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1. Martin Sheen

Total Arrests: 66

Actor Martin Sheen has more been arrested more times than any other celebrity; however, unlike most celebrities, the reason that he has been arrested so many times is because of his social and political conscience – he loves protesting. He was first arrested in 1986 for protesting President Ronald Reagan’s Star Wars Initiative and his most recent arrest was in 2007 when he and 38 other activists trespassed at the Nevada Test Site.

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