A-List Justice

The Most Arrested Celebrities

Being part of a much-loved Hollywood dynasty has helped Charlie Sheen survive and prosper despite years of bad behavior. But how long will his family keep rallying behind him?

Gus Ruelas / AP Photo

Gus Ruelas / AP Photo

#1, Martin Sheen

Total Arrests: 66


Rap Sheet: The actor famous for a slew of roles including President Bartlet on The West Wing and Captain Willard in Apocalypse Now has another claim to fame: the Hollywood celebrity with the most arrests. He admitted in 2009 to being put in handcuffs a whopping 66 times. Of course, his crime of choice happens to be protest; his most recent arrest in 2007 was for trespassing on a Nevada nuclear test facility. His first arrest dates back to 1986 when he was pinched for civil disobedience while protesting Ronald Reagan's "star wars" initiative.

#2, DMX

Total Arrests: 13


Rap Sheet: By The Daily Beast's count, DMX has been arrested more than a dozen times for everything from felony drugs charges, cocaine possession, criminal impersonation, and reckless driving and parole violation. One of his notorious arrests occurred in 2004 when he allegedly crashed his SUV through a parking lot gate at New York's Kennedy airport after telling the security guard he was a government agent. The police report alleged that the rapper, aka Earl Simmons, ordered a driver in a different parking lot to exit his vehicle and identified himself as an FBI agent.

#3, Snoop Dogg

Total Arrests: 8


Rap Sheet: Snoop Dogg's criminal history started in 1993 when he was arrested for murder for his alleged connection to the death of a rival gang member who was shot by Snoop's bodyguard. He was later cleared of all charges related to the case. His other arrests include charges of firearm possession, felony drug possession, and trespassing.

#4, Bobby Brown

Total Arrests: 7


Rap Sheet: Gaining fame as a member of the boy band New Edition, Bobby Brown may be better known today as the bad boy ex-husband of Whitney Houston. Brown was arrested in 2003 for misdemeanor battery for allegedly hitting Houston. Prior to that, he had been caught by the cops and arrested for speeding, driving without a license, and possessing marijuana.

#5, T.I.

Total Arrests: 7


Rap Sheet: Clifford Harris, Jr, aka T.I., has been involved in a slew of arrests since his debut album was released in 2001. In 2007, he garnered headlines for winning a Grammy Award for Best Rap Solo, the release of his fifth album and for an October arrest that took place hours before the BET Hip Hop Awards. He was charged with two felonies related to weapons possession. He was eventually sentenced to an indeterminate prison term, a year of house arrest and community service. He spent nine months in jail.

#6, Robert Downey, Jr.

Total Arrests: 6


Rap Sheet: Revered as one of Tinseltown's most talented actors, Robert Downey, Jr.'s struggles with the law and addiction are all part of the lore. For a string of years in the late '90s, he seemed to be forever in and out of rehabilitation facilities and jail. During a comeback stint in 2000 with a part on the television series Ally McBeal, for which he was nominated for an Emmy, he was arrested twice on drug-related charges and booted from the show. Since then, he has reportedly remained sober and his career has once again flourished.

#7, O.J. Simpson

Total Arrests: 5


Rap Sheet: "The Juice" may now be better known for his run-ins with the law than his career as a running back. Simpson was arrested in June 1994 for the murder of his ex-wife Nicole Brown and Ronald Goldman, a charge which culminated in the "trial of the century" that ended in a verdict of "not guilty" for Simpson. He wasn't so lucky with a 2007 arrest for armed robbery and kidnapping—charges for which he's now serving time in a Nevada jail after being found guilty in 2008.

#8, Mike Tyson

Total Arrests: 7


Rap Sheet: Though the famous heavyweight champion is reported to have been arrested 38 times by the time he became a teenager thanks to a young career in petty crimes, he's been arrested seven times since becoming the youngest heavyweight champion in history at the age of 20 in 1986. He has been arrested for felony drug possession, assault and battery, as well as the famous arrest in 1991 for the rape of Miss Black Rhode Island, a charge for which he was convicted and served three years in prison.

#9, Lil Wayne

Total Arrests: 4


Rap Sheet: At age 9, Lil Wayne became the youngest member of the rap label Cash Money Records and his debut album sold more than 1 million copies, but his musical career isn't the only thing that started early. In July of 2007, Lil Wayne, then 24 years old, was arrested after a performance in New York City for criminal possession of a weapon and marijuana. In October of that year, after a concert in Boise, Idaho, Lil Wayne was arrested on felony charges of possessing a controlled substance; the charges were later dropped. He was arrested again in January 2008 when Border Patrol pulled over his tour bus and found marijuana, cocaine, MDMA and tens of thousands of dollars in cash.

AP Photo

#10, Sean Penn

Total Arrests: 6


Rap Sheet: The Oscar-winning actor who may be best known for roles in the classic movie Fast Times at Ridgemont High and the critical darling Milk also has a reputation as an angry person. He has been known to lash out at the persistence of the press and the paparazzi. He was arrested for assaulting a photographer in 1986 and was eventually sentenced to 60 days in jail for violating probation. Earlier this year, the actor pleaded no contest to a misdemeanor vandalism charge that resulted from a fight with a paparazzo in October 2009.

#11, James Brown

Total Arrests: 8


Rap Sheet: To most he's known as "The Godfather of Soul," but James Brown also has a reputation for getting pinched. He was arrested multiple times on charges of assault by his ex-wife Adrienne Rodriguez, but his most notorious arrest occurred in 1988 when he was arrested after a high-speed car chase between Georgia and South Carolina—Brown drove on his rims—and charged with assaulting a police officer as well as weapons, drug and driving offenses. He eventually served three years of a six-year prison sentence for the incident.

#12, Foxy Brown


Total Arrests: 7


Rap Sheet: Foxy Brown grew up in Brooklyn attracting notice after winning a local talent contest. Small successes led to her being signed by Def Jam Records when she was 17 years old in 1996. But troubles with the law soon followed. She was arrested following a scuffle with hotel staff in North Carolina in1997 and for driving without a license in Brooklyn in 2000. She attracted publicity when she allegedly attacked two manicurists in New York City in 2004; she pleaded not guilty but was ordered to endure three years of probation and take anger-management classes.

Jeff Christensen / AP Photo

#13, George Michael

Total Arrests: 7


Rap Sheet: As part of the pop group Wham!, George Michael became a star, but his various arrests made him internationally notorious. He was arrested by an undercover cop in 1997 in Los Angeles for "engaging in a lewd act" in a public park restroom. On separate occasions in 2007 and 2008, he was pinched for drug possession, and was arrested most recently this July and charged with possession of marijuana and driving under the influence of drugs.

#14, R. Kelly

Total Arrests: 3


Rap Sheet: After a decade of musical success, R. Kelly's legal troubles started in 2002, when a videotape was released that allegedly showed him having sex with a 14-year-old girl. Kelly denied being the man in the video. He was arrested in 2002 for having sex with a minor—charges which he was later absolved of in trial. He was also arrested in 2003 for child pornography, but the charges were later dropped.

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#15, Lindsay Lohan

Total Arrests: 5


Rap Sheet: Hard-partying starlet Lindsay Lohan just can't seem to get her act together. The paparazzi favorite has been in and out of rehab since her first DUI arrest on May 26, 2007. After being fitted with a SCRAM bracelet to monitor her sobriety, the Mean Girls star was busted two months later for DUI and felony cocaine possession, resulting in her third stint in rehab, according to People magazine, and, ultimately, a whopping 84 minutes in jail. At her July 6 probation revocation hearing, a judge sentenced Lohan to 90 days in jail for violating the terms of her probation stemming from her July 2007 arrest. She only ended up serving 14 days of the sentence due to overcrowding, but was ordered to submit to random drug testing—testing that she ended up failing, she revealed, on September 17 via Twitter, according to CNN. You can now find Lohan at the Betty Ford Center where she's been ordered to stay until January 3, 2011, reported CNN, with her next court hearing scheduled for February 25, 2011.

#16, Rip Torn

Total Arrests: 4


Rap Sheet: Rip Torn has quite a temper. When filming Maidstone in 1970, the actor allegedly struck the film's director, Norman Mailer, with a hammer, and then attempted to bite his ear off, according to The Huffington Post. The star of The Larry Sanders Show and NBC's 30 Rock has also suffered a series of DUI-related arrests, including a 2004 bust where the actor crashed his car into a New York City taxi cab under the influence, resulting in not only one of the greatest mug shots ever, but an epic rant against the cops back at the station. Even with all that, his latest arrest is the most puzzling, as Connecticut state police allegedly found the actor so intoxicated on the night of January 29, that he broke into a Connecticut bank with a loaded gun thinking it was his home in Salisbury, Connecticut, according to The Independent.

#17, Charlie Sheen

Total Arrests: 3


Rap Sheet: Like father, like son? He doesn't quite measure up to pops, but Charlie Sheen is no stranger to run-ins with the law. Despite his well-known love of working women and the rumored incident where he shot ex-fiancé Kelly Preston in the arm, the Two and a Half Men star has by-and-large avoided jail. But his recent incident at the Plaza Hotel in New York City that allegedly found the actor naked and intoxicated with a porn star locked in his bathroom—resulting in a weekend hospital stay—should come as no surprise. The actor has a long history of drug problems including a 1998 cocaine overdose, as well as a pair of arrests for domestic violence. Despite all his troubles, Sheen is remarkably resilient. He'll be returning to the set of Two and a Half Men next Tuesday, according to People magazine.

#18, Paris Hilton

Total Arrests: 3


Rap Sheet: Despite heavy media coverage, the ubiquitous, hell-raising socialite has only been arrested a grand total of three times. Following a September 2006 DUI arrest and subsequent probation violations, Hilton was forced to serve 45 days in jail, reportedly shrieking, "It's not right!" and hugging her mother when the verdict was given. Her most serious offense came when, on August 26 of this year, she was arrested inside the Wynn resort in Las Vegas and a small bag of cocaine dropped out of her purse in front of the police lieutenant, according to the Associated Press. The heiress avoided felony drug possession charges—and jail time—by copping to a pair of misdemeanors, and has been noticeably absent from the club scene since.

#19, Naomi Campbell

Total Arrests: 3


Rap Sheet: In addition to allegedly receiving blood diamonds from deposed dictators, this glamorous supermodel is known for her fiery temper, resulting in a string of arrests for assault. The most eye-opening incident occurred in March of 2006, when Campbell reportedly hurled a Swarovski crystal-encrusted mobile phone at her housekeeper in her swank, Park Avenue New York City condo. In addition to mandatory anger management classes, she was forced to perform community service for the crime—which she, naturally, attended in stilettos, according to People magazine.

#20, Michelle Rodriguez

Total Arrests: 5


Rap Sheet: The Fast and the Furious not only describes this tough girl actress' arrest history of DUI arrests, but also her time spent in jail. The Avatar star has had several run-ins with the law, mostly related to charges of driving under the influence of alcohol. In May 2006, she served just four hours and 20 minutes of a 60-day jail sentence for violating probation stemming from a DUI arrest while filming the ABC TV series Lost in Hawaii in December 2005, and in January 2008, the actress was released from jail just 18 days into a 180 day sentence for violating her probation in a DUI case thanks to overcrowding, according to the Associated Press.

AP Photo

#21, Amy Winehouse

Total Arrests: 5


Rap Sheet: The talented R&B/Jazz crooner has, despite her passionate pleas on hit single "Rehab," had numerous stints at treatment facilities for her drug addiction. She's also been arrested a total of five times for everything from suspicion of smoking crack on video and allegedly hitting a woman in the eye during the 2008 Prince's Ball to " perverting the course of justice." However, the singer is now reportedly clean, telling the U.K. edition of Glamour in its November issue, "I used to use drugs and I haven't used drugs in almost three years. I literally woke up one day and was like, 'I don't want to do this anymore.'"

#22, Charles Barkley

Total Arrests: 4


Rap Sheet: The basketball legend has been anything but civilized in the past, no doubt hurting his alleged dreams of one day running for governor in his home state of Alabama. His feisty on-court demeanor also extended outside the lines, as the former athlete has chalked up a variety of arrests, the most puzzling of which occurred on New Year's Eve 2008, when Barkley was arrested on drunk-driving charges. When he got back to the DUI Taskforce command post, Barkley reportedly told police, "I was going to drive around the corner and get" oral sex, said the police report. He then told a civilian employee, "I'll tattoo your name on my ass" if it would get him out of the DUI, according to the report.