Saying Lindsay Lohan has had a rocky career is like saying the sky is blue. At least she can take solace knowing that she doesn't have the longest rap sheet on this list, but she's certainly done some embarrassing things (and we're not just talking about her filmography).
After back-to-back DUI arrests within two months of each other in 2007, Lohan's long drug rehabilitation stint and probation timeline began. Lohan has been arrested a whopping six times during her time in the limelight. She's appeared in court 20 times and spent 42 days in jail, which is nothing compared to the 300+ she was sentenced to.
Rodriguez's appearance on this list may not exactly come as a surprise since she's known for playing a badass character that doesn't take "no" for an answer. Guess an attitude like that doesn't crossover that well when you're dealing with the police. Like some others on this list, her arrests were DUI related.
While most of her five arrests were because of driving while under the influence, she has also been known to break probation and assault her roommates, both of which also landed her in jail. Fortunately for her (and not so much the drivers on the street), she's been let out early every time due to overcrowding. During one famous stint, she spent only four hours in jail after a DUI and hit-and-run.
George Michael wasn't a stranger to the police station. He famously had trouble with drugs and alcohol, which led to many of his arrests. Sadly, he passed away in 2016, but he still stands as one of the most-arrested celebrities in history, with five total on his record.
Most of his issues stemmed from his substance abuse, but he was also once arrested for lewd conduct and soliciting public sex. Honestly though, what did we expect from someone who had gyrating hips that would make Elvis jealous? This kind of stuff seemed right up his alley.
Winehouse was famous for saying she wouldn't go to rehab, so it shouldn't be a huge shocker that the singer has been arrested multiple times for drug-related offenses. There was also an incident of assault in 2008 when she allegedly hit a woman in the eye. Winehouse was truly a wild child.
Sadly, this lifestyle would catch up to her. In 2011, she passed away from alcohol poisoning. She was just 27 years old, meaning she became the newest member of the 27 club, which features famous members like Jimi Hendrix, Janis Joplin, and Jim Morrison.
You know the Juice had to be on this list. At one time, OJ was incredibly famous for his sports career, and that translated into an...interesting acting career. Then, we all know what happened. OJ hit legal troubles — that's a little bit of an understatement, we think.
Now, he's known as the guy who allegedly murdered his ex-wife Nicole Brown and Ronal Goldman (which he was, of course, memorably found not guilty by the jury). In total, OJ Simpson has been arrested six times. He's spent nine years in jail, with his court case only taking 252 days.
Sean Penn may not look it, but he's always been kind of a psycho. Sure, he's an Oscar winner, but that hasn't done much for his reputation. The guy is famous for beating the crap out of people, including his ex-wife Madonna during one incident. While we'd love to say he went to jail for that, but Madonna asked the DA to drop the charges.
In total, he's been arrested six times, including an assault on two photographers, which he attacked with a rock for taking pictures. Another was a misdemeanor vandalism charge for fighting yet another journalist. Guess he isn't a huge fan of the paparazzi.
We love a guy that's turned his life around. Robet Downey Jr is now one of the most famous actors in the world, but he had an extremely rocky start. When Downey first got his start, he had major issues with drugs and alcohol. He was arrested a total of six times.
All this happened in the '90s, and you'd think that he was headed for an early grave. Thankfully, he turned his life around. Much of his recovery is due to his wife, and Downey has said so on several occasions. It took a lot of hard work, but we're glad he figured his life out.
If you don't know who Foxy Brown is, don't feel bad. She's a rapper, but that's hardly what she's known for. If anything, she's famous for having run-ins with the law and high-profile celebrity feuds. It seems like Brown just can't keep herself out of trouble.
Currently sitting at a whopping seven arrests, Brown has a record of anger management issues. Most of her bookings have been for attacks on hotel staff, manicurists, and other service industry professionals. Yikes! That makes Foxy Brown the worst Karen of them all. Foxy, they're just trying to do their jobs!
James Brown may be known as the Godfather of Funk, but he's apparently a Godfather of going to jail, too. Anyone that knows about music knows that Brown had a history of drug abuse and domestic violence — often, the two were linked. Brown's wives often cited cruel treatment, and one of which had him arrested after he got high on PCP and had a violent outburst against her.
Another common arrest was unlawfully using and owning weapons. Still, his most infamous event was an arrest after a high-speed chase, which led to a six-year prison sentence. In total, James Brown was arrested eight times.
T.I. has had quite a few run-ins with the law. Real name Clifford Harris, he began having trouble at the age of 14 when he was already arrested several times for dealing drugs. This continued through adulthood, including in the Grammy-winning rapper's most noted arrest that came just hours before he was to appear at the BET Hip Hop Awards.
In total, T.I. has been arrested eight times, including two felonies. The reasons for arrest range from dealing and holding drugs, purchasing guns (with one time being Harris trying to buy a gun from a federal agent), and assault. In 2010 alone, he was sentenced to 11 months in jail.
A musician in his own right, Brown may be more famous as the ex-husband of the late Whitney Houston. His seven arrests include a misdemeanor battery (against Houston), drug possession, and driving offenses like speeding and not having his license.
Somehow, Brown has gotten even more popular from all the jail time he's dodged. He's spent most of his life in and out of jail. While it isn't clear how long he's been behind bars, we know he had a "string of arrests" in the '90s. Then there was the 75-day sentence in 2000 (of which he only remained in jail for 39 days).
Would you believe that Snoop Dogg has been arrested for felony drug possession? We weren't surprised either. We were surprised that his eight total arrests included firearm possession and trespassing, as well as being picked up in connection to the death of a rival gang member (for which he was cleared of all charges).
Snoop Dogg has managed to turn his reputation around, though. While many fans still love him for his hard lifestyle, others can't help but watch him and Martha Stewart make gift baskets together on her TV show. Yeah, you read that right. Guess prison really changes a person. Some make music while others make wreaths.
At this point, it would be easier to list all of the crimes that DMX hadn't gotten in trouble for. The artist was in jail a total of 30 times on various offenses, including robbery, assault, pretending to be a federal agent, carjacking, animal cruelty, failure to pay child support, reckless driving, driving under the influence, unlicensed driving, drug possession, probation violation, and tax evasion.
That's...uh — that's certainly something! Many of his arrests occurred before he got famous, but they didn't stop after he reached the top. In 2021, DMX passed away from a cocaine-induced heart attack. The biggest shock with this news was that he made his way to age 50 with his hard lifestyle.
Mike Tyson has a bit of a strange reputation. Younger generations don't know much about his past, but older generations know exactly what this former professional boxer has done wrong. Tyson's arrest for assault and battery didn't come as a surprise since he was known for beating people up for a living.
The man has had seven arrests in his history. The actual crimes range from felony drug position to the 1991 arrest for the r*pe of a Miss Black America contestant. As a teenager, Tyson admitted that he was arrested 38 other times! Holy crap!
Maybe some of you saw this one coming while others didn't expect Martin Sheen to be the one with the most arrests on record! With 66 arrests, Martin Sheen leads the list by far. But it's not what it may seem at first glance. He's certainly on this list for a different reasons compared to others.
As an activist, Sheen isn't arrested for drug use or violence against others. Quite the opposite. The vast majority of the arrests, if not all, are thanks to civil disobedience and protest, resulting in bookings such as "trespassing." Some of the things he's protested include protesting against nuclear power, nuclear weapons testing, dangerous arms buildup, abuse of farmworkers, and Canadian seal clubbing.
