What don’t celebrities have? They have money, fame, glory, and freedom to do whatever the heck they want. And sometimes, it gets them into trouble. Legal trouble. There are quite a few celebrities who have rap sheets. Famous bad boys and girls, like Lindsay Lohan and Robert Downey Jr., come to mind.
But there are others you would never imagine getting their hands cuffed behind their backs. These stars were booked for drugs, theft, assault, and even murder. Some never made it behind bars while others certainly did. This is a list of the most arrested celebrities. And the top three might just surprise you.
40. Martha Stewart
No. of Arrests: 4
Latest Arrest: 2001
Leave it to America’s (seemingly) most innocent celebrity to land herself in prison. What got her in there? She lied about stocks. In late 2001, Martha Stewart sold about 4,000 shares of ImClone Systems, a company that develops cancer-therapy drugs and was run by her friend Sam Waksal.
The next day, the stock tanked. Waksal was arrested on charges of insider trading and sentenced to seven years in prison. Stewart was questioned in June 2002, denied any insider knowledge, but was investigated by the Department of Justice. She was then indicted on charges of securities fraud and obstruction of justice. In July 2004, she was sentenced to five months in prison, five months of home confinement, and fined $30,000.
39. Ozzy Osbourne
No. of Arrests: 4
Latest Arrest: 1984
Ozzy Osbourne, the godfather of heavy metal and frontman of Black Sabbath, was as much of a bad boy as he looked. The crazed singer has something of a criminal past, despite being near the bottom (or top) of this list.
February 19, 1982 was the day that Ozzy got so drunk that he wore a woman’s dress. He also had a full bladder and relieved himself at the Alamo Plaza (the site of the Alamo battle of 1836). Ozzy ended up in jail for the rest of the day. Two years later, he got booked for public intoxication while stumbling around Memphis.
38. Danny Trejo
No. of Arrests: 4
Latest Arrest: 1960s
Danny Trejo has made a remarkable recovery after years spent in prison. He went from street criminal to one of Hollywood’s most seen actors. He was first arrested at 10 years old, when he was already using drugs. He got caught for selling them.
As he got older, he found himself in juvenile hall, and in there, he stabbed a sailor in the face with a piece of broken glass. As a result, he was given an additional ten years. He was later put in solitary confinement for hitting a prison guard. He was finally released in 1969 and has never looked back.
37. A$AP Rocky
No. of Arrests: 4
Latest Arrest: 2022
On April 20, 2022, the 33-year-old rapper and Rihanna’s baby-daddy, A$AP Rocky, was arrested at Los Angeles International Airport after walking out of his private jet. It had to do with a shooting from the year before. The shooting victim, who survived, told police that A$AP “approached him with a handgun on the street” and a friend of the rapper’s shot him three to four times.
A$AP was also arrested in 2019 for an assault in Sweden and held in a “horrific” facility with “24/7 solitary confinement.” In 2013, he faced charges after slapping a fan at the Made in America Festival, and in 2012, he was cuffed after a street fight with photographers in New York City.
36. Charlie Sheen
No. of Arrests: 4
Latest Arrest: 2009
Charlie Sheen has been known for a lot of things, one of them being his wild side (remember tiger blood?). He’s been in the headlines for his drug abuse, relationships, legal struggles, his HIV diagnosis, and his arrests.
2009 was the latest arrest for Sheen, when he was arrested on Christmas Day in Aspen and booked on suspicion of second-degree assault and menacing and criminal mischief in a domestic-violence dispute. With whom? His wife, Brooke Mueller. Apparently, he threatened to kill her with a knife. Mueller told the 911 dispatcher that he had “some switchblade” and that “right now we have people who are separating us, but I have to file the report.”
35. Bill Gates
No. of Arrests: 4
Latest Arrest: 1977
The tech giant is one of the richest people in the world now, but back in the 1970s, police didn’t expect too much of him. Recently, in early 2021, a rumor started about Bill Gates being arrested for a knife attack in Nebraska, but it proved to be just that – a rumor.
The Microsoft man was arrested in 1977 for… a traffic infraction. He was living in Albuquerque, New Mexico at the time. On the night of December 13, Albuquerque police booked the scrawny kid into jail and produced one of the most viral mug shots in the history of the internet.
34. Paris Hilton
No. of Arrests: 5
Latest Arrest: 2010
Paris Hilton was known as a wild child socialite. She’s come a long way, though, and is now quite the businesswoman in her 40s. But in her 20s, she got arrested multiple times, including one time that led to a mug shot that went viral.
Hilton’s first arrest was in 2006 for “driving erratically.” In 2010, she was booked again at a FIFA World Cup game in South Africa on suspicion of possession of cannabis. Two weeks later, she was arrested again for possession (and released shortly after).
33. Conor McGregor
No. of Arrests: 5
Latest Arrest: 2022
The UFC champ has been a notorious bad boy, but it got to the point that he was investigated for sexual assault. After the first of such charges, he was released after questioning. But a second sexual assault charge came in October 2019.
It was reported that a “woman in her 20s was sexually assaulted in a vehicle parked outside a Dublin pub.” He was arrested but never charged. McGregor was also charged in 2019 for punching an older man at a bar in Dublin. His latest arrest was in 2022 for “alleged road traffic violations,” also in Dublin.
32. Mick Jagger
No. of Arrests: 5
Latest Arrest: 1972
Of course, there was the infamous drug bust in February 1967, when Mick Jagger and Keith Richards got booked in their apartment for drugs. But Jagger’s latest arrest was five years later, in 1972, in Warwick. Both Jagger and Richards were arrested again.
This time, they were cuffed for assaulting a Providence Journal photographer while the band was shipping up to Boston for a concert. It was Richards who took the swing, but Jagger called out to the police, “If you take him, you’re taking me, too.” So, the whole band was placed in custody.
31. Winona Ryder
No. of Arrests: 5
Latest Arrest: 2001
Back in 2001, Winona Ryder made headlines when people learned that the actress shoplifted, of all things. She stole merchandise worth $5,560 at the Saks Fifth Avenue store in New York City. She was charged and found guilty of theft and had to serve 480 hours of community service.
For years, Ryder refused to speak about it. In 2013, she finally spoke up. She told Interview Magazine that she was thankful for the incident. “That thing that happened, I was starting to have some trouble before that. I think a lot of people think that is what sort of sent me off in another direction, but I was actually starting to have some trouble a few years before,” she said.
30. T.I.
No. of Arrests: 5
Latest Arrest: 2018
Rapper, actor, activist, and now comedian (apparently), Clifford “T.I.” Harris has some arrests under his belt. He’s been booked for drug possession, carrying a weapon, violating parole, and illegally purchasing a firearm.
2018 seems to be his last brush with the law, when he was arrested outside of the gated community he lives in, in Atlanta. The rapper was charged with public drunkenness, simple assault and disorderly conduct. The security guard wouldn’t let him into the community, and after an argument with the guard, he was arrested.
29. Robert Downey Jr.
No. of Arrests: 6
Latest Arrest: 2001
He got big in the ‘80s, only to land himself in jail in the ‘90s. In 1996, People reported that Downey had “[become] the most recent casualty of Hollywood’s heroin resurgence.” That year, he faced two felony charges and three misdemeanors – for driving under the influence, possession of illegal drugs, and carrying a handgun in his truck.
He served less than a year in jail before being bailed out. In 2000 and 2001, he was busted again for illegal substances. By 2003, he announced that he was done with drugs, having tossed his whole supply into the ocean.
28. Paul McCartney
No. of Arrests: 6
Latest Arrest: 1984
Paul McCartney wasn’t the only Beatle to get into some legal trouble. The Fab Four were known for their reckless lifestyle: smoking, drinking, and doing drugs – before and after they became superstars. As for McCartney, he’s been arrested a total of six times, beginning at the age of when he was 18.
His last known arrest was in 1984, when he and his wife Linda were busted in Barbados for marijuana possession. It came exactly four years after the most notorious of his legal woes, when he was caught by customs officers at the Tokyo airport who found weed in his luggage. In fact, they found enough to charge him for smuggling. McCartney spent nine days at the Tokyo Narcotics Detention Center before he was released and deported.
27. Jane Fonda
No. of Arrests: 6
Latest Arrest: 2019
Jane Fonda is also a committed activist – so much so, that she gets arrested for it. Each of her arrests has been related to her political work. It started in 1970, when she was traveling around the country protesting the Vietnam War.
Her final arrest came on December 19, 2019, the day before her 82nd birthday. People sang “Happy Birthday” as she was led away by the police. Just like her infamous 1970 mugshot, Fonda’s red coat, black beret, and handcuffs became a Halloween costume.
26. Lil Kim
No. of Arrests: 6
Latest Arrest: 2001
Lil Kim is another one of the few on this list that actually made it to prison. While she’s been arrested six times, she was imprisoned once, in 2006, for one year and a day (and she had to pay $50,000).
After a shootout in 2001, she was convicted of three counts of perjury and one count of conspiracy of perjury. The shootout was over insults that were written into the rapper’s song lyrics. Lil Kim is lucky, as she was facing closer to 20 years behind bars.
25. Chris Brown
No. of Arrests: 6
Latest Arrest: 2019
Chris Brown knows the legal system well; he’s been leading a criminal life for years in addition to his successful music career. Everyone knows the serious brawl he and Rihanna had back in 2009, but he’s been arrested since then.
In January 2019, Brown was detained in Paris when a woman filed a rape complaint with the police. He was being charged with aggravated rape and drug infractions. Brown denied the accusation, sharing a photo with the caption, “This B***h Lyin” and “I WANNA MAKE IT PERFECTLY CLEAR…… THIS IS FALSE AND A WHOLE LOT OF [CRAP]! NNNNNNNNEEEEEEEEEEVVVVVVVVVVEEEEEERRRRRR!!!!!!”
24. Floyd Mayweather Jr.
No. of Arrests: 6
Latest Arrest: 2011
Professional athlete Floyd Mayweather Jr. has had his run-ins with the law. One of his six arrests led to him serving time in prison. In 2002, he was charged with two counts of domestic violence and misdemeanor battery.
His last arrest came in 2011, when he was again charged with misdemeanor battery as well as a felony battery charge. He was sentenced to a correctional facility for attacking his ex-girlfriend, Josie Harris, in front of their children. He was given a 90-day term, with 100 hours of community service, a 12-month domestic-violence program, and a $2,500 fine. He served 60 days.
23. Michelle Rodriguez
No. of Arrests: 7
Latest Arrest: 2004
Michelle Rodriguez, known for her recurring role in Fast and the Furious as well as Lost, started a 180-day jail term in LA in 2007 for a probation violation. She was violating her probation for charges of previous offenses for drunk driving and a hit-and-run.
In 2004, she made a plea of no contest (the equivalent of guilty) to three traffic offenses. But due to overcrowding, Rodriguez was released after just four hours and 20 minutes.
22. Christian Slater
No. of Arrests: 7
Latest Arrest: 2005
Can we all agree that Christian Slater is one of the more surprising additions to this list? In 2005, long before Me Too came to be, the actor was arrested and charged with sexual abuse and “forcible touching” when a woman accused him of groping her butt.
Then 35, Slater was arrested shortly later on Manhattan’s Upper East Side. He was released on no bail and at the bail hearing, he shouted: “This is bull … I didn’t do anything – I’m going to sue everybody.” In 1997, he was also arrested for assaulting his girlfriend and was sentenced to 90 days in jail after he pled no contest.
21. Lil Wayne
No. of Arrests: 7
Latest Arrest: 2019
In 2020, Lil Wayne was charged with criminal possession of a firearm, and since he’s a prior felony offender, he was facing 10 years in prison. The rapper, whose name is Dwayne Carter, was arrested in 2019 at the Opa Locka Executive Airport.
Lucky for him, he was pardoned by then-president Donald Trump on January 19, 2021, on his last full day in office. Back in 2010, the rapper served a year in Riker’s Island for pleading guilty to possession of a weapon.
20. Vanilla Ice
No. of Arrests: 7
Latest Arrest: 2015
Vanilla Ice, whose real name is Robert Van Winkle, may be a one-hit wonder, but he has had more than one hit with authorities. in 2015, he was arrested for burglary in Florida. The then-47-year-old stole several household items from a Palm Beach County residence in its foreclosure.
Ice was apparently filming an episode of his reality show, The Vanilla Ice Project, where the has-been rapper showed off his handyman skills, fixing up homes he hoped to flip.
19. Amanda Bynes
No. of Arrests: 8
Latest Arrest: 2014
Amanda Bynes surprised most of her fans when she did a 180 and became a criminal after her childhood fame as a Nickelodeon kid. Her diehard fans, though, have stuck with her through her years-long conservatorship.
Come 2010, she announced her retirement from acting. It was then that her spiral downward began. Her last arrest was in 2014 when she was caught with a DUI, again. In March 2022, she was finally released from a conservatorship when a judge deemed that she had “done everything the court has asked over a long period of time.”
17. 50 Cent
No. of Arrests: 8
Latest Arrest: 2016
Curtis James Jackson III, aka 50 Cent, made a transformation from drug dealer to hip hop artist. By 12, he was selling drugs. At 19, he was arrested for the first time. He pled guilty and went to boot camp to avoid jail.
His final arrest was in 2016 for the use of profanity in St. Kitts, where swearing in public is banned. He used the word “mother f*****” on stage and was immediately arrested. In 2020, Page Six reported that the rapper used his prison experiences as inspiration for his series, For Life.
16. Justin Bieber
No. of Arrests: 8
Latest Arrest: 2014
The world-famous pop star was 19 years old when he got booked on a number of charges, including suspicion of drunk driving, drag racing, driving without a valid license and resisting arrest.
He was shown to have Xanax and marijuana in his system when he was pulled over in Miami. A (now viral) video showed him at the police station taking a sobriety test and doing push-ups. His mug shot sees him grinning from ear to ear. He later referred to it as “not my finest hour.”
15. Marilyn Manson
No. of Arrests: 8
Latest Arrest: 2019
The bizarre musician has been on the hot seat for sexual assault among other offenses. He’s faced multiple sexual and physical abuse accusations – all of which he denied. Manson (Brian Warner) was dropped by his record label after Evan Rachel Wood, his former fiancé, accused him of “horrific” abuse.
In 2021, he surrendered on an outstanding warrant connected to a concert in August 2019. He had been arrested on two counts of misdemeanor assault. “It is no secret to anyone who has attended a Marilyn Manson concert that he likes to be provocative on stage, especially in front of a camera,” his lawyer stated.
14. Mike Tyson
No. of Arrests: 8
Latest Arrest: 2022
Everyone knows Mike Tyson is a force to be reckoned with. Even though he’s changed his ways and is a lot less violent than he was in his early years, he’s still raking in arrests. This year, he was involved in an incident on a plane.
During a Jet Blue flight to Miami, a video captured a man being punched by Tyson after the man had “badgered” the Hall of Fame boxer. The man was seen harassing Tyson and throwing a water bottle at him. Both men were detained at the airport and later released.
13. Sean Penn
No. of Arrests: 8
Latest Arrest: 2018
As recently as 2018, Sean Penn and his son Hopper (with Robin Wright) were arrested on drug charges. A third person, Uma Von Wittkamp, was arrested with them. All three were released from jail after posting $25,000 bonds.
Penn, his son, 24, and Von Wittkamp, 26, were arrested in Nebraska after getting pulled over for failure to signal. The officer then suspected drug activity. In the car was 14g of marijuana, 4 amphetamine pills, and 3g of psilocybin mushrooms.
12. OJ Simpson
No. of Arrests: 9
Latest Arrest: 2020
No, this isn’t about the major murder trial in the ‘90s that put him in prison for years – we all know about that. O.J. Simpson, now in his 60s, is still getting into trouble. He was arrested in 2020 and held without bail for armed robbery involving sports memorabilia in a Las Vegas hotel.
He was charged with two counts of robbery and two counts of assault with a deadly weapon, conspiracy to commit burglary and burglary with a firearm. It was said that he had gone to the hotel room to collect memorabilia of his – that he didn’t break into the premises.
11. R. Kelly
No. of Arrests: 9
Latest Arrest: 2019
Of all his creepy crimes, R. Kelly was charged with prostitution in 2019. In 2001, he was accused of hiring a teenage prostitute who asked him for an autograph. He allegedly then invited the 17-year-old to his hotel room and offered her $200 to get undressed and dance with him.
Come June 2022, and the singer was finally sentenced to 30 years in prison for using his celebrity to sexually abuse minors and women. The judge said the singer had an “indifference to human suffering” – that he used sex as a weapon. She said in court, “You taught them that love is enslavement and violence.”
10. Snoop Dogg
No. of Arrests: 9
Latest Arrest: 2012
Rapper and producer Snoop Dogg (Calvin Cordozar Broadus, Jr.) may not enjoy the process of getting handcuffed and having his prints taken, but Snoop sure knows what it’s like to get arrested.
He was 19 when he got booked in 1990 for cocaine possession. Three years later, he was booked for being a member of LA’s gang the Crips. In 2012, he was caught for marijuana possession. Despite all his run-ins with the police, he’s still one of the most successful and wealthiest rappers in the world (with a net worth of $150 million).
9. Tekashi 6ix9ine
No. of Arrests: 10
Latest Arrest: 2020
It seems like more people know of Tekashi 6ix9ine’s rap sheet than his actual music. The rapper and his security guards, one of whom is a former New York City detective, were arrested for “robbing a man after chasing him through Harlem in SUVs with flashing lights and sirens” in August 2020.
They were charged with robbery and criminal impersonation (pretending to be the cops). The incident was caught on tape and went viral. When Tekashi 6ix9ine’s (Daniel Hernandez) entourage saw the man try to record the rapper on his cell phone, “they shouted at him and began to chase him as he drove away.”
8. Courtney Love
No. of Arrests: 10
Latest Arrest: 2004
Whether you love or hate her, Courtney Love has a presence that extends beyond her music. Some people say she should be arrested for the murder of her husband, Kurt Cobain (which was never proven), but the Hole singer was booked for other misdemeanors.
Her last arrest was back in 2004, when she was booked at Plaid, a New York City nightclub, for reckless endangerment. During her performance, she tossed a microphone stand into the audience, striking someone in the head, according to police records.
7. Lindsay Lohan
No. of Arrests: 10
Latest Arrest: 2012
She’s been arrested 10 times, most of which seem to have taken place in 2012. In March, Lindsay Lohan sideswiped a person with her car and fled the scene. That same month, she completed her probation only to go back into one for necklace theft.
In September 2012, she was arrested for clipping a man with her car and, once again, fleeing the scene. In October, she and her mother got into a fight that the cops were called about. And then in November, she punched a woman in the face at a club. What gives, Lohan?
8. Shia LaBeouf
No. of Arrests: 11
Latest Arrest: 2020
Here’s another Disney child who seems to like getting into trouble. When the former Even Stevens star was arrested at age 20, it was already his third time getting handcuffed. This time, he wasn’t shoplifting; he was thrown in jail for a couple days after trying to stab a neighbor.
He was arrested for refusing to leave a store, driving under the influence, getting into fights, and even performing on Broadway while intoxicated. His last arrest occurred in 2020, when he was booked for misdemeanor battery and misdemeanor theft.
6. Dennis Rodman
No. of Arrests: 14
Latest Arrest: 2019
Hall of Famer Dennis Rodman has been known for his odd behavior and off-the-court problems. But none of his crimes were ever major offenses. In 1999, cops arrested him and his then-estranged wife, Carmen Electra, at a hotel in Miami Beach after getting a call about a physical altercation between the stars.
In 2019, when Rodman was celebrating his 58th birthday, he was accused of slapping someone at the bar twice. Despite apologizing, prosecutors charged him with one count of misdemeanor battery, but he entered a plea of not guilty.
5. Bobby Brown
No. of Arrests: 14
Latest Arrest: 2020
The famous battering ex-husband of Whitney Houston has been known as a guy with a rap sheet. He’s been arrested for misdemeanor battery, like in 2003, when he was cuffed after hitting Houston during an argument. He was taken into custody in 2004 and 2007 for not paying child support to Kim Ward, the mother of his children.
In 2020, Bobby Brown was arrested on suspicion of DUI, which was the second alcohol-related arrest that year. Police pulled him over for driving erratically. He’s been open about his battle with addiction…
4. Suge Knight
No. of Arrests: 15
Latest Arrest: 2015
Death Row Records’ Suge Knight was apparently involved in a deadly hit-and run in 2015, when he reversed his car and hit two bystanders. One of them, actor Terry Carter, 55, died shortly thereafter, and the second, actor Cle Sloan, 51, was injured.
Knight turned himself in the next day. In 2018, Knight was sentenced to 28 years after he pled no contest to involuntary manslaughter. Due to his previous felonies, he was given a harsher sentence.
3. DMX
No. of Arrests: 24
Latest Arrest: 2017
The late rapper developed quite the rap sheet before passing away in 2021 (he died of a heart attack assumed to have been caused by an overdose). DMX was incarcerated at least 30 times in his life for numerous crimes.
He first went to prison in 1986 after stealing a dog from a junkyard. Two years later, he was back in jail for stealing a car. He had some serious offenses, like animal cruelty, drug possession, resisting arrest, reckless driving, driving without a license, disorderly conduct, possession of a weapon, tax evasion, and failure to pay child support.
2. Pete Doherty
No. of Arrests: 26
Latest Arrest: 2019
The Libertines frontman was arrested for his connection with the drug death of filmmaker and heiress Robin Whitehead. Of all his arrests, the dude has never spent more than 14 weeks in prison. He usually gets a fine and a slap on the wrist.
In 2019, he was arrested twice in Paris over the course of three days. Police stopped him during an alleged cocaine purchase. His second arrest was when he went out to celebrate, got drunk, and started a brawl with a man who pressed assault charges.
1. Martin Sheen
No. of Arrests: 66
Latest Arrest: 2020
Like Jane Fonda, Martin Sheen’s arrests stem from his passion for politics and protesting. And getting booked 66 times puts him at the top (bottom) of this list. He even wears his rap sheet like a badge of honor.
In 2020, he was arrested in a climate protest organized by Jane Fonda in Washington D.C. He and 146 others were arrested for “crowding, obstructing or incommoding.” During his speech, he told the crowd, “Let our country awake.” I guess it’s all worth it for Mr. Sheen.