15 Celebs Who Were Arrested Over 5 Times

Let's face it, how many of us have done something that we could have been arrested for, at least once? We all screw up from time to time. Sometimes we mess up in a small way, like forgetting to send your mom a card on Mother's Day, other times our screw ups are a little bit bigger, and we break the law and get arrested. Now, this is not to say that it is okay to get arrested; that all depends on the situation, really. But sometimes when someone gets arrested it is that slap to the face that reminds them that they have been on the wrong track, and it turns into the chance for them to turn their life around.

But what if that person gets arrested and never learns? What if they just keep on doing the same old stupid things, over and over again. When is it too much? When is it obvious that the person really is just a total mess? Is it when they get arrested twice, three times? Maybe four?

The people on this list laugh at four arrests. Getting arrested four times? "Those were the good old days..." All of the people on this list have been arrested at least five times. These people are like the original gangsters of the celebrity world; some of them are true straight-up criminals, while others are just such messes they can't get out of their own way. All of them seem to be unable to "Walk the line" as the saying goes. Here is our list of the 15 most wanted celebs who are in the exclusive "Been arrested five or more times" club.

15 O.J. Simpson- 5


How could a list like this exist without having O.J. Simpson on it? You didn't think he was just a plain, old, alleged murderer did you? Oh heck no, he has been arrested numerous times for a whole bunch of different things.  For those of you not in the know, O.J was not only one of the best football players of all time, he also had a very successful acting career and also was a well-known sports announcer. He was first arrested for the murder of his wife, and of her friend Ron Goldman. He walked on those charges but since then he has been arrested for battery and burglary,  possession of ecstasy and money laundering. He was  speeding in a boat, and then finally was arrested in 2007  for charges including robbery and kidnapping. He is currently doing a 33-year prison sentence; it could not have happened to a nicer guy.

14 Michelle Rodriguez- 5


Next on the list is Michelle Rodriguez. One probably would not think The Fast and the Furious star Michelle would come in next on a list that features accused murderer O.J Simpson, but hey, we aren't here to judge, just to point out that Michelle has been arrested numerous times, and boy, has she. She first was busted for an assault after she and her roommate threw hands at each other. Then  she was charged with eight misdemeanors, and a DUI charge. Later she got popped for another DUI that got her a bit of jail time. Finally she was arrested for violating her probation and was sentenced to 180 days in jail. She only served 18 because of overcrowding and has stayed out of trouble ever since. Should we be impressed?

13 Lindsay Lohan- 5


How many stars have had a bigger fall from grace and have become a bigger joke than Lindsay Lohan? After being the child star of The Parent Trap and the teen star of Mean Girls Lindsay seemed to have it all going on, then she started getting busted left and right.  She was first arrested for a DUI in 2007 then got her second DUI shortly thereafter and was also arrested for cocaine possession.  She later was busted for violating her probation She was sentenced to 90 days in jail. Her most recent  arrest went down in 2015. Come on Lindsay, pull it together, who do you think you are, Snoop Dogg? Actually, she probably does not think she is, since he has way more arrests than she does, but you will have to read on for that one.

12 Robert Downey Jr- 6


Now most of you that are a bit younger just think of Robert Downey Jr. as a handsome actor and action star. Those of us who are a little older think of him as a guy who is seriously lucky he is not in prison right now. The dude was arrested six times. In 1996,  he was arrested for possession of heroin, cocaine, and a firearm on Sunset Boulevard. Not a good look Robert.  He was sentenced to probation and also had to have court-ordered drug testing. His next arrest went down when he blew off the drug testing. He then spent six months in jail. He got popped again in 2000 with a bunch of drugs in a hotel room. Then a few months later he got busted again for the same thing. Just when everyone thought it was all over for him, he pulled it together and has stayed sober now for years.

11 Sean Penn- 6 (Allegedly)

Compared to the rest of the people on this list, Sean might be a bit of a surprise. Although there are numerous reports out there, such as one on Buzzfeed that says "He's been arrested six times," the word is that a lot of these arrests have been pushed under the rug. He was first arrested for attacking a photographer,  and then was thrown in jail for a parole violation. But his most famous assault was on his then-wife, Madonna. There are also many other arrests that he says are not true, but many close to him admit that they are. He seems to have chilled out a bit, but hey, this is still the guy that hung a photographer over a 9th floor balcony according to his own biography. Let's just say that Mr. Penn has been arrested a lot and leave it at that for now. We don't want him to come "visiting."

10 Vanilla Ice- 6


The funny thing about Vanilla Ice is that he kind of gets it both ways. On the one side are people that kind of make fun of him for being a white rapper, and a gangster wannabe. Which seems pretty accurate, honestly. But the thing is, when you have been arrested six times you are not a wannabe, you kind of are a gangster. His first arrest was for illegal drag racing. Then he ramped it up a bit and got busted for threatening a homeless man with a gun. Then he got bagged for assaulting his wife, then once again got busted for assault on his wife. Then finally he was popped February 2015 when he robbed a Florida home. A lot of these charges were dropped, but again, we are talking about arrests, not so much about convictions. That is another story for another day. Ice, you are a bad man!

9 T.I- 7


Rapper T.I became popular in the late 1990s with hits like “Whatever You Like." His real name, meaning the one on the arrest record,  is Clifford Joseph Harris, Jr. He takes it up a notch with his very impressive criminal record which includes seven arrests. Way to go, Cliff! It all started when he was a teen and was busted for dealing drugs. He eventually violated his probation and was sentenced to three years in prison. Then in  2007, he was arrested for felony weapon possession and went to jail for nine months. In between there was a whole lot of other stuff, which earns T.I a spot on this list. I mean, come on, man, it is one thing to keep doing all this awful stuff, but maybe you can get better at not getting caught for it?

8 Foxy Brown- 7

So we hate to admit it but some of these people just are not all that nice. You might have guessed that anyway, but the reality is that some of these folks just have some problems while others, like Foxy Brown, are really just kind of total jerks. Her first arrest happened when she spat on employees at a hotel who told her there was not a way to iron her clothes. See what I mean about the jerk thing? Then she was arrested for driving without a license after she crashed her car. She next assaulted  a police officer at an airport. She got busted for many other things of this nature including attacking two manicurists in 2004 and a beauty store clerk in 2007. So the lesson of this is, if Foxy Brown calls and wants to make an appointment with you to have her hair and nails done, hang up the phone as quickly as you can.

7 George Michael- 7

Now when you really think about it, would you guess that this pretty boy, the former lead singer of the band Wham, would wind up on this list?  At one point Michael was one of the most popular singers in the world, but hey, drugs are a pretty terrible thing.  His first arrest was for lewd conduct at a public restroom in Beverly Hills- you can let your imagination help you figure out what that was all about. He was then arrested in 2006 for possession of prescription drugs, then he was busted for driving under the influence, then he got arrested again at a public restroom, this time with drugs. Hey George, stay out of public men's rooms and you will be fine! He was busted numerous other times, did some prison time, then went to rehab in 2010 and seems to be doing fine now.

6 Bobby Brown- 7


Now, while a lot of these people are a bit of a surprise, there is no surprise at all about Bobby Brown being on this list; for a while it seemed like he was getting busted just about every day.  While once best known for being one of the world's most popular singers, both solo and with New Edition,  he was busted numerous times for things like  driving under the influence or possession of crack cocaine. In 2003, Brown assaulted his wife Whitney Houston, which once again let us all know that famous people could be even more messed up than we were. He was arrested more times for DUI, but then went to a long alcohol-rehab program that seems to have kept his head on straight, for now anyway. Let's hope that continues.

5 James Brown- 8 


James Brown was nothing short of a legend. Just like some of the younger R&B stars like Bobby Brown were trying to catch James Brown's legacy in music, they also could not keep up with him in arrests. James Brown is the first on this list who had eight arrests. James Brown was truly a bad man, with many drugs and weapons charges, some of which even involved police chases. He was pretty into PCP, which is really not a good thing to be into. At all.  While using PCP, he was arrested for domestic violence numerous times; sometimes he even beat his wife with a lead pipe. In 2004 he was busted again for domestic violence. If he had not died in 2006 who knows how many more times he would have been busted? The whole thing is a drag, since as a performer Brown was amazing. As a human being? Not so much.

4 Snoop Dogg- 8


Now Snoop is probably the only guy on this list that you don't care about. Eight arrests for Snoop Dogg? Who cares right? Snoop Dogg is cool!  He first was arrested as a teen for possession of cocaine, then spend a lot of the 1990s in and out of prison while working with Dr. Dre to get his music career rolling. Once he was a big star he kept getting busted, once for having a gun in his car. Many of his arrests involved weed of course, but he also has been busted for having cocaine and firearms. He and a bunch of buddies were also arrested for vandalism in a London airport. But hey, this is all just Snoop being Snoop, right? Well, he was also arrested in 1993 for his involvement in a murder. But you know: "La Di Da Di, we likes to party. We don't cause trouble, we don't bother nobody."

3 DMX- 13


Now we get into the real heavy hitters. 13 arrests? What? If there is one thing that is for sure, rapper and actor DMX does not care about a whole lot.  He has been busted for weapons charges, animal cruelty, identity falsification, and drug possession, among many other things. He had a good one in  2004- he got busted for being under the influence with a gun while trying to  steal a car at the airport in New York while also pretending to be a federal agent. Really, dude?  Lately, it has been even more, as he's been getting busted with charges like resisting arrest, driving under the influence, and possession of drugs with the intent to sell. He also has been busted for failing to pay child support. Come on man! Pull it together!

2 Mike Tyson- 40


I could have done this whole article about Mike Tyson and all the times he has been arrested. Tyson was without dispute one of the very best boxer in the world. When he fought he was the real deal, no one wanted a piece of him. And for good reason, this dude is nasty and crazy. Most of his 40 arrests happened before he even became famous- he was busted close to 40 times as a teenager for fighting and other petty crimes. He then was arrested for rape and did three years in prison, and has also been busted for driving under the influence and cocaine possession. Estimates range anywhere from 30 to 50 arrests, it is hard to tell as many of them happened when he was underage. Tyson is supposedly sober now, but it is still hard to imagine him making it through the rest of his life without ever getting busted again.

1 Martin Sheen- 66


So apparently Charlie Sheen gets at least a part of his personality from his dad. These guys just simply do not like to follow the rules. Sheen has been arrested 66 times, which sounds awful except for the fact that he wanted to be busted every single time. The thing is, Martin Sheen is a human rights activist and every single one of his arrests came from him protesting something that he found to be unjust. His arrests are all for trespassing, civil disobedience, and disturbing the peace. So, while Martin Sheen holds the all time record for celebrity arrests, Mike Tyson is the one who leads the list for actual serious crime. Although Martin Sheen is responsible for Charlie Sheen, and that should be a crime of some sort all by itself.

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15 Celebs Who Were Arrested Over 5 Times