15 Celebrities Who Have Been Arrested Multiple Times

It's one thing to make a mistake and find yourself behind bars, but it's altogether different if you're a prominent member of society. That one mistake may be enough to derail your entire career. There are many examples of celebrities who were unable to overcome their demons, proving that no matter how talented you are, you aren't immune from failing.

It's even worse when you don't just make one mistake but many, especially when it's the same mistake, like driving under the influence, that has clearly plagued your personal life.

There are some people on this list who, despite their arrest records, are respected members of society. You just may view them a little bit differently when you realize how many times they've been behind bars. Here are 15 celebrities who have been arrested multiple times. Included as well is a description of some of their most outrageous criminal acts, such as when Iron Man decided to do some drugs and wander into a stranger's house.

Think you know who number one may be? Here's a hint: he's been in over 200 films and/or television shows but he's been arrested an astonishing 66 times!


15 Lindsay Lohan


Who doesn’t love watching Lindsay Lohan in the Parent Trap or Mean Girls? That just makes her fall from grace all the sadder to take.

In 2007, she was arrested for a DUI. This normally wakes people up but two months later, she was arrested for another DUI and cocaine possession. As part of her probation, she was also sentenced to random drug testing, which she failed.

Lohan was also arrested in 2010, after it was found that she violated terms of her probation by missing several mandatory classes. It was this incident that led to her getting sentenced 90 days in jail, but left after only 23 days due to overcrowding.

She has been able to keep her nose clean since, so here’s hoping she’s starting to turn a corner.

14 Charlie Sheen


Charlie Sheen may have seemed to go off the deep end as of late, but his arrest history suggests that he’s always had some issues. In 2009, Sheen was arrested after assaulting his wife, Brooke Mueller. He ended up agreeing to a plea deal that dictated 30 days of probation, 30 days in drug rehab and 36 hours of anger management.

This was not the first time that Sheen has been charged with this crime. In 1996, he was arrested after beating his adult film star girlfriend, Brittany Ashland, who stated that he slammed her into the marble floor and threatened to kill her.

In 1998, he nearly overdosed on cocaine, resulting in Martin Sheen turning him over to authorities and Charlie Sheen being placed in rehab.

Sheen was not arrested for this one but there was an incident at the Plaza Hotel in New York, in which he caused over $7,000 in damages.

In 2011, a restraining order by Mueller was placed against Sheen, preventing him from coming within 100 yards of her and their twin sons. The order was granted after Sheen made specific and descriptive threats against her.

13 Paris Hilton


If you are currently the star of a TV show, it might be smart to try to keep out of trouble, even if that show is The Simple Life and you're Paris Hilton. Paris clearly did not heed that advice though and, in 2006, she was arrested after driving under the influence and having a blood alcohol content of 0.08%. It ended up leading to her license being suspended and forced the production team to alter the shooting schedule of season 5 of The Simple Life.

In 2010, Paris was arrested on suspicion of cocaine possession after it was found in a purse that belonged to her. Her original defense literally included the statement, “This purse in question was a high street brand – and by no means up to my high fashion standards."

No wonder that didn’t go over well, especially when Paris later claimed that some of the items in the purse were hers (like the money and credit cards) but that the cocaine was not.

This ended up being a further complication when Paris tried to fly into Japan, but they have strict drug laws and often deny anyone who has a drug history entry into the country.

12 James Brown

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James Brown may be the Godfather of Soul but that does not make him exempt from doing some really awful things.

In the mid 1980s, Brown was arrested four times between 1987 and 1995 for violence against his wife, Adrienne Rodriguez. This included an incident in 1988, in which he hit her with a lead pipe and shot at her car during a fight.

Brown battled addiction issues for most of his life and that also has a way of landing you in a jail cell. He was arrested only one week after leaving rehab in 1998 for unlawful use of a handgun and having possession of cannabis.

Brown’s past also includes arrests for drugs and weapons charges but the peak came in 1988, when he engaged in a high-speed car chase with officials. He was convicted of having an unlicensed pistol then assaulting a police officer, as well as various drug-related and driving charges. He ended up serving two years of his original six-year sentence for the charges.

11 Sean Penn


If you are the paparazzi, you might not want to piss off Sean Penn. He was arrested in 1987 after a violent outburst on a film set, during which he assaulted a photographer.

This also came out around the time when there were reports that he was abusing Madonna, his wife at the time. Madonna has recently stated that those allegations were completely outrageous.

In 2010, he faced up to 18 months in jail after he was arrested on charges of battery and vandalism. The incident, which was captured by TMZ, showed Penn kicking a photographer and breaking his camera.

10 George Michael


George Michael may have risen to stardom because of his role in the music group Wham! but that’s also the sound that he heard as his jail cell closed.

Michael was arrested back in 1997, after performing a lewd act in a public washroom. Michael stated that he went into the washroom when a cop followeed him and played the game "I'll show you mine, you show me yours, and then when you show me yours, I'm going to nick you!"

His arrest was influential in him feeling comfortable enough to come out of the closet.

In 2006, he was arrested for possession of Class C drugs, but was released after he was cautioned by police.

Michael has also openly battled marijuana addiction and, in 2007, was arrested after motorists reported a car obstructing the road at traffic lights. Michael admitted to being unfit to drive and was banned from driving for two years.

Michael had also been arrested on suspicion of being unfit to drive on July 4th, 2010 after returning from the Gay Pride Parade.

9 Mike Tyson


Like many individuals on this list, Tyson has a criminal past that started at a young age. By the time he was 13, he had been arrested 38 times. It was in juvenile detention that he got "discovered."

His most serious allegation came in 1991, when he was arrested for the rape of 18-year-old Desiree Washington. This led to Tyson being sentenced to six years in prison and four years of probation.

He has also pleaded guilty in the past to drug possession and driving under the influence. He made it easy for police officers, as he told them he was addicted to cocaine and had been using it when they pulled him over.

Tyson was also arrested in 2006, when he nearly crashed into a police SUV after leaving a nightclub.


8 Lil Wayne


Lil Wayne made his mark as a rapper before the age of 10, but he’s also not been afraid to make his mark in a jail cell.

Wayne has been arrested 4 times, the most significant in 2007 when he was arrested for smoking marijuana and when police were searching him, they found a gun. Carrying a gun might make you seem like a bad ass but it is also illegal if it is not registered. Wayne ended up serving a one-year sentence.

Wayne was arrested later that same year on felony fugitive charges from the Georgia police, who stated he had a controlled substance on him. Thankfully for Wayne, the department said it was a mix-up and the charges were dropped.

He was not so lucky in 2008 when his tour bus was stopped, and officials discovered 105 grams of marijuana, 29 grams of cocaine, 41 grams of ecstasy and $22,000 in cash. He ended up agreeing to a plea deal for the charges and served 36 months of probation.

7 O.J. Simpson


Did you know that O.J. Simpson was trialed for murder? Obviously you did, because his trial was only one of the biggest in history!

While he was acquitted of the murders of Ronald Goldman and Nicole Brown, he was unable to keep out of trouble. In 2007, he was charged with armed robbery and kidnapping after he attempted to steal back some of his old sports merchandise. He was sentenced to nine years without parole.

In 2001, Simpson was arrested again for simple battery and burglary when he yanked the glasses off of another motorist during a traffic dispute. It sounds minor but if the courts had ruled against him, he could have faced sixteen years in prison.

He’s also been arrested for speeding through a manatee protection zone but, in hindsight, that’s probably not so bad.

6 Robert Downey Jr.


As talented an actor as Robert Downey Jr. is, the man had to overcome some huge demons to get to where he is.

From 1996 to 2001, Downey was arrested several times on drug-related charges. His past addiction included usage of marijuana, cocaine and heroin.

Downey was arrested in 1996 and not only had heroin and cocaine on him but also an unloaded .357 Magnum! Within a month of this arrest, he was arrested again for violating parole after he was under the influence, wandered into a neighbor's house and fell asleep on their bed.

Things ended up working out for him though and, within a week of his release in 2000, Downey landed the role on Ally McBeal which helped turn his life around.

5 T.I.


T.I. was rapping by the age of 8, and by the time he was only 14, he had been arrested several times. Things get more serious as you get older though, and T.I.’s peak may have come in 2007. He was arrested after federal authorities found three unregistered machine guns and two silencers. He was also charged with possession of firearms by a convicted felon. He received one year of house arrest, an undefined prison sentence (that ended up being 9 months) and community service.

In 2010, he was also arrested on drug charges in Los Angeles. This would have landed him 11 months in prison for violating the terms of his probation, but the charges were dropped. He has been arrested in the past for also failing to meet the terms of his probation.


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It normally only takes one serious arrest to make you want to reevaluate your life, but I suppose things are different when you’re a rap star. DMX has been arrested 13 times with charges ranging from cocaine possession, criminal impersonation, and parole violation.

His crowning moment came when he crashed his car through John F. Kennedy International Airport and when confronted by someone, lied and told them that he was a government agent. Apparently what X "gon' give to ya" is a pair of handcuffs.

3 Snoop Dogg


Snoop Dogg may seem like an easy going individual (perhaps it’s the weed) but in 1993, things were far from going smoothly. He was arrested after an alleged connection was made in regards to the death of a local gang member. Snoop was cleared of all charges when it came out that it was his bodyguard who shot the man. I mean, still not great but at least it allowed him to not spend life behind bars!

As well as this, Snoop has also faced charges of firearm possession, felony drug possession and trespassing.

2 Bobby Brown


Bobby Brown was no stranger to having a hit song, but unfortunately that was not the only area where he knew how to have a hit, as he was arrested for battery in 2003.

Brown has been arrested 7 times, but the most notable came in 1996 when he was arrested after a high-speed chase that led to him crashing his wife’s Mitsubishi. After the crash, he then resisted arrest and peed on the back of one of the squad cars.

Brown also has several incidents with driving under the influence, including being arrested for it twice in 2012.

1 Martin Sheen


Martin Sheen may not look like a typical badass, but there is no doubt that he does knows what the inside of a jail cell looks like.

Sheen is also no stranger to political activism causes, some of which land him in hot water. Sheen stated back in 2009 that he had been arrested 66 times for various crimes, such as civil disobedience or trespassing. Now to be fair, there are far worse things to be arrested for but the high total makes Sheen worthy of being the top spot on the list.

Kudos to his son Charlie for trying, but he's still got a long way to go to top his Dad.

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