Popular Culture

10 Celebrities Who Have Been Arrested More Times Than You Might Think Wise


Anyone can get arrested once. Have a bad day, get pulled over for speeding, say something stupid and you might find yourself cooling your heels in the cells. However, as Jack’s aunt once said; “Once is unfortunate, twice smacks of carelessness.” most people who get into trouble with the law – try to avoid doing so again in the future. Not these 10 celebrities who have been arrested rather more times that you might think wise.

Sean Penn (6 times)


Sean Penn has definitely mellowed in his old age but he was once the raging nutcase husband of Madonna with a reputation for attacking the paparazzi every time they came near him. His first arrest was in 1986 for a rumble with a photographer – his last in 2009 for umm… assaulting a photographer. He has done a slight amount of time in jail over the years. While we wish Sean all the best in his career; we recommend that you ask for a selfie with him with complete caution. You never know when you’ll wake the inner beast that lays dormant beneath the smooth exterior.

Robert Downey Jr. (6 times)

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The current Iron Man of the movies was once a total pain in the backside. His drug and alcohol problems are well documented and it’s possession that has seen Downey Jr. arrested 7 times in the past. During one period of relative sanity he landed a role on Ally McBeal (the 90s legal drama) and was so good that he was nominated for an Emmy. That success didn’t stop him from going on to get himself arrested twice in a short period and then he was dismissed from the show. The positive news is that unlike many on this list – Downey has rehabilitated and is doing very, very well for himself indeed nowadays.

George Michael (7 times)


George was once the clean cut darling of millions in the band Wham! Then he kind of fell to pieces for a bit. George’s arrest record contains at least one unfair conviction; the one for “engaging in a lewd act” which appeared to be both entrapment and an act of homophobia on behalf of the law. However, it’s hard to be as forgiving about the rest of his crimes which include drinking under the influence and multiple counts of drug possession.

Mike Tyson (7 times)


Our celebrity rapist is Mike Tyson; who might be higher up our celebrity arrest list if we were allowed to count all the times he was arrested in his teens (more than 30 arrests) but it’s really not done to add child crimes and it’s not as if Mike’s adult arrest record makes him a better person. Apart from the rape of Miss Black Rhode Islands (for which he did 3 years in prison) – he’s been regularly arrested for assault and for drugs charges. Fortunately, there are some things your career doesn’t recover from and rape is one of them. Mike Tyson got his just desserts in more ways than one.

Bobby Brown (7 times)

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The former spouse of the tragically deceased Whitney Houston; it’s hard to find anything nice to say about this woman beating, drugged up lunatic and fortunately we don’t have to – Brown has been arrested for battery, driving with no license, possession and more. Considering he rebuilt his career on Whitney’s success – you’d think he’d have been more grateful wouldn’t you?

T.I. (7 times)


You’re definitely getting it wrong when you get arrested 7 times and T.I. was just getting it right in the rest of his life before he picked up an indeterminate term for weapons trafficking. He’d won a Grammy Award for the best rap record of 2001 for a solo artist. But that was where the career highlights would come to an end.

James Brown – The Godfather of Soul (8 times)


Sharing the honors of third place in our chart – we have James Brown. James was a busy boy when he wasn’t being the Godfather of Soul; mainly because he spent 6 years in prison for his 8 arrests. He assaulted a police officer, his ex-wife and anyone else he could lay his hands on. He also got arrested for a car chase, drugs and weapons.

Snoop Dogg (8 times)


Another entry, another rapper. You’d think there was something about singing about drugs and violence that made people take drugs and be violent. Snoop Dogg (or Snoop Lion as he now prefers it) has been charged for murder but convicted for cocaine possession among other things. He’s such a complete disaster that he’s been banned from entering the United Kingdom and Australia.

Earl Simmons – DMX (13 times)


DMX, the rapper, is without a doubt the most reckless and feckless person on our list; even though his arrest record makes him the second most arrested celebrity. He’s been nicked for cocaine possession, reckless driving and a bunch of other stupid stuff. He’s also been arrested for impersonating an FBI agent when he smashed his SUV through a parking lot gate in an airport. You have to give him full marks for creativity – even if you don’t want to give him marks for anything else.

Martin Sheen (66 Times!)


Nobody comes close to being arrested as many times as Martin Sheen which might come as a shock to people who follow Charlie Sheen’s antics in the press. However, this isn’t because Martin is a “bad boy” like some of the other people on our list – in fact he’s never really done anything that you might call bad. What he does do is protest. He’s happy, now that he’s hung up his acting boots, to protest in favor of any cause he passionately believes in. So all his arrests come from trying to do good – the baddest boy on the list is actually the goodest (which is a word that we made up for this sentence).


Melissa Stenson
Melissa Stenson is a senior writer at PopCrunch. She covers movies, tv, and music news. She also writes engaging and fun lists about various pop culture events.

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