Slammer, joint, con college, hole, pen, pokey or farm – whatever you call it, chances are that getting arrested and going to jail aren’t at the top of anyone’s list when it comes to being successful and living a good life. However, statistics show that half of the men in the United States have been to jail with an even unluckier 30 percent of men who have criminal records in addition to spending time behind bars.
While most people think that celebrities can get away with anything simply because they can buy their way out of trouble, that’s not always true and, in those 50 percent of men, celebrities are also included! With the world watching their every move, celebs can’t get away with changing their hairstyle much less doing something illegal which is why many celebrities who get caught often learn their lesson after their first offense. But for some, the lesson takes a little longer to sink in.
Though we’ve all seen celebrities like Mel Gibson and Justin Bieber getting arrested, we couldn’t help but wonder about celebrities who have made more than a couple of trips to the slammer. Which celebrities have the longest rap sheets and who just might surprise you? Let’s take a look at the top 20 most arrested celebrities of all time!
#20 – R. Kelly
Though some might assume that R. Kelly would be closer to the top of our list, the King of R&B has actually only been arrested three times during his 27-year career. A Chicago native, Kelly was a rising star when he was first arrested in July 1996 after a brawl fight at a gym in Lafayette, Louisiana led to one year of probation for battery. His next arrest came just two years later in 1998 when he picked up three misdemeanor charges for disorderly conduct, including a noise ordinance for playing his music too loud. Luckily, the charges were dropped months later.
Well beyond any noise violation or gym brawl, Kelly’s most notable and shocking arrest occurred in 2002 when a disturbing video was released that showed him with an underage girl. With the video released in February as he opened the 2002 Winter Olympics, Kelly was arrested four months later and charged with 21 counts of child pornography. After numerous delays, the trial finally occurred in 2008 as a jury found Kelly not guilty on all counts.
#19 – Paris Hilton
“That’s hot!” Living proof that orange just might be the new black, heiress and socialite Paris Hilton brought the family legacy to an entirely new level after rocking the orange jumpsuit three different times. First arrested in 2006 for driving under the influence while filming The Simple Life, Hilton’s blood alcohol content was right at the legal limit of 0.08 percent but her license was still suspended as she faced 36 months on probation and $1,500 in fines.
Accustomed to getting her way, Hilton didn’t take the charges seriously and violated her probation multiple times which prompted her second return to jail and 45 days in lockup, which ignited a media frenzy. Hilton managed to stay on the straight and narrow until 2010 when she was in Las Vegas with her boyfriend when a bag of cocaine fell out of her purse in front of a police officer. To avoid felony charges, the celebutante pled guilty to two misdemeanors, paid $2,000 in fines and completed 200 hours of community service and rehab.
#18 – Josh Brolin
Ending a three-way tie on our list with three arrests is Men in Black 3 and No Country for Old Men star Josh Brolin. Marrying actress Diane Lane in August 2004, it was only four months later in December when police were called to their home after an altercation that led to Brolin’s first arrest and charges of domestic battery. Despite Lane calling the police, she ended up dropping the charges claiming it was nothing more than a marital misunderstanding.
By 2008, Brolin was in handcuffs once again only this time he was with actor Jeffrey Wright and the W film crew when a fight broke out in a Shreveport, Louisiana bar. After posting a bond of $334, Brolin was released and the charges were dropped. Obviously with a nose for trouble, Brolin’s most recent arrest occurred in 2013 on New Year’s Day when he was arrested for public intoxication in Santa Monica, California in what would become the start of a very difficult and self-destructive year.
#17 – Lil’ Wayne
One of the best-selling artists of all time known for hits like “Lollipop” and “Got Money,” Lil’ Wayne ups the ante in terms of rap sheets with a total of four arrests. Wayne’s first arrest came in New York City in 2007 when police found him smoking marijuana outside his tour bus. Once in custody, police discovered weapons on the bus and charged Wayne with criminal possession that landed him in a prison cell on Rikers Island for one year in 2010.
By October 2007, Wayne was arrested again after playing a concert in Boise, Idaho when he was accused of possessing a controlled substance. The charges were later dropped but Wayne had bigger problems in 2008 when his bus rolled up to border patrol in Yuma, Arizona where authorities discovered multiple drugs and thousands of dollars in cash. Despite being charged with numerous offenses including four felonies, the lesson was lost on Wayne who found himself in a similar situation with the Texas border patrol in 2009.
#16 – Rip Torn
Becoming a household name in the 1980s for his role in Cross Creek, Elmore “Rip” Torn, Jr. went on to star in hits like The Larry Sanders Show and Men in Black while earning a different kind of fame among police thanks to his four arrests. Earning the reputation of having a short fuse early in his career, Torn’s first arrest came in 1970 when he attacked director Norman Mailer on the set of Maidstone with a hammer.
Managing to stay out of trouble until 2004, Torn was arrested for a DUI in New York City after hitting a taxi cab only to follow up the incident with a second offense. His most famous arrest occurred in 2010 when he was so drunk that he mistook a bank for his home and broke into the branch office carrying a gun. To avoid serving a 30-month prison sentence, Torn pled guilty to all the charges, agreed to rehab for alcohol abuse and served three years of probation.
#15- O.J. Simpson
From winning a Heisman Trophy at the University of Southern California to being drafted to the NFL’s Buffalo Bills, O.J. Simpson’s life after football fame has been a sordid and tragic affair. Simpson’s first arrest in 1994 resulted in the trial of the century when he evaded police after being accused of killing his wife, Nicole, and her friend Ronald Goldman. A year later, a jury acquitted Simpson of all charges but that did little to motivate him to turn his life around.
Instead, Simpson has spent even more time in handcuffs after five arrests that eventually landed him in a prison cell. Arrested in 2001 for battery and burglary, Simpson was taken in once again months later for possession of ecstasy and money laundering. The following year, the former football star was arrested for speeding in a boat with his most recent (and final) arrest occurring in 2007 in Las Vegas when he was charged with multiple felonies that led to a 33-year prison sentence in Lovelock, Nevada where he remains today.
#14 – Michelle Rodriguez
Joining the strange but true category, Fast & Furious star Michelle Rodriguez has as many arrests as O.J. Simpson but, unlike Simpson, she’s managed to finally turn her life around. Handcuffed for the first time in 2002, Rodriguez was arrested for assault after a fight with her roommate turned south. Just over a year later, she was charged with eight misdemeanors after a hit-and-run incident that led to a DUI charge and two days in prison.
Problems continued for Rodriguez in 2005 after being pulled over numerous times with her legal troubles coming to a head in December when she was arrested for another DUI that resulted in jail time, community service and rehab. In 2007, Rodriguez was arrested for violating her probation and was sentenced to 180 days in jail but only served 18 days as a result of overcrowding. Luckily, her career in Hollywood has taken off keeping her too busy to find time for any more trouble.
#13 – Lindsay Lohan
The last celebrity on our list with five arrests is former child star Lindsay Lohan who won the hearts of audiences with her freckle-faced grin on The Parent Trap in 1998. Becoming a teen icon in films like Mean Girls, things seemed to be going well for Lohan until 2007 when she was arrested for a DUI and forced to wear a bracelet that monitored her blood alcohol level. Obviously not learning her lesson, Lohan got her second DUI two months later in addition to cocaine possession that led her right back to rehab.
After violating her probation and admitting her addiction to alcohol and drugs, Lohan was sentenced to 90 days in jail only to serve two weeks before failing another drug test. Spending the next few years in and out of rehab, the former star has been on and off probation for the better part of the last decade with her most recent pending arrest coming in 2015 after she barely completed her court-ordered community service. Maybe one day she’ll get her life back on track!
#12 – Robert Downey Jr.
Known today as Marvel Comics’ bad boy billionaire Tony Stark and Iron Man, Robert Downey Jr. hasn’t always been a welcome sight in the Hollywood spotlight. With half a dozen arrests on his record, Downey’s rap sheet started in 1996 when he was arrested for possession of heroin, cocaine and a firearm while speeding down Sunset Boulevard. Sentenced to probation and court-ordered drug testing, Downey skipped out on one of the tests three years later only to find himself in handcuffs with six months to spend in jail.
On an extreme path to self-destruction, Downey’s next arrest occurred in November 2000 when police found him under the influence and surrounded by drugs in a hotel room. A few months later, a similar situation occurred leading to a five-year span of multiple arrests that brought Downey to the lowest point in his life and career. Obviously hitting rock bottom, Downey has been sober since 2003 and has made a huge comeback as one of the biggest stars in Hollywood today.
#11 – Sean Penn
Perhaps a surprising addition to our list, Academy Award winner Sean Penn definitely lives up to his bad boy reputation with a total of six arrests, if not more, on his record. First arrested 30 years ago after assaulting a photographer and being sent to jail for violating his parole, Penn became notorious for having a violent personality as rumors spread that he even hit his wife, Madonna, in fits of uncontrollable rage.
With only the assault on the photographer and his probation violation confirmed, there are multiple arrests that Penn denies being true but many close to the actor have admitted that he has done several short stints in jail for domestic assault only to have the charges swept under the rug. Penn’s denials of these claims has been so vehement that he once sued television and film producer Lee Daniels for $10 million for defamation of character. Sounds like that’s a touchy subject!
#10 – Vanilla Ice
With “Ice Ice Baby” as one of the biggest hits of the 1990s, Robert Matthew Van Winkle skyrocketed to stardom better known by his stage name, Vanilla Ice. Joining Sean Penn, Robert Downey Jr. and the others in the half-dozen club, Ice’s first arrest came in 1998 when the Dallas native was arrested in his hometown for illegal drag racing. Three years later, he was handcuffed once again after threatening a homeless man with a gun.
Surprisingly enough, Ice managed to stay out of trouble for a decade before landing himself back in jail after assaulting his wife while driving, which resulted in court-ordered therapy. Seven years later, Ice was charged a second time for assault on his wife but the charges were later dropped after witnesses confirmed it was only a verbal disagreement. His most recent arrest occurred in February 2015 when he robbed a Florida home. These charges were also dropped after Ice completed 100 hours of community service and paid for the stolen items.
#9 – T.I.
Coming in with seven arrests on our list, Clifford Joseph Harris, Jr. made his hip hop and rap debut as T.I. in the late 1990s when he escorted in a new genre known as trap music with hits like “Whatever You Like.” Long before stardom, however, T.I. had already started a record of his own as a teen when he was convicted and placed on probation after being busted as a drug dealer. By 2004, T.I. violated his probation and, with a warrant out for his arrest, was eventually caught and sentenced to three years in prison.
While the Grammy Award winner was preparing for the BET Hip Hop Awards in 2007, he was arrested by police for felony weapon possession and spent nine months in jail. Needless to say, between drugs and firearms, T.I. has been in trouble with the law for over 21 years which has brought him a great deal of negative publicity not to mention the loss of millions in endorsement deals. Maybe it’s time for T.I. to stop living his lyrics!
#8 – Foxy Brown
Far less famous than T.I., Foxy Brown is a rapper, model and actress best known for hits like “I’ll Be” and “Hot Spot.” Born in The Big Apple, Brown’s series of seven arrests began on the road in 1997 at a hotel in North Carolina when she spat on employees after being told there wasn’t a way to iron her clothes. Sadly, we aren’t joking! In 2000, Brown was arrested for driving without a license after she crashed her Range Rover in Brooklyn.
Gaining a reputation for her obscene and explosive personality, Brown’s rap sheet grew again in 2002 when she stirred up trouble in Jamaica after dodging a mandatory body search at the airport and assaulting a police officer. With more assaults and probation violations to follow over the next decade, Brown attacked two manicurists in 2004 and a beauty store clerk in 2007 that led to jail time, 76 days of solitary confinement and anger management classes.
#7 – George Michael
Leaving America and traveling across the pond to Great Britain, best-selling singer and music icon George Michael has also been arrested seven times over the course of his 35-year career. In 1998, Michael seemed to come off of the rails a bit after he was arrested for lewd conduct at a public restroom in Beverly Hills. Since then, the majority of his arrests and legal battles have centered on a common problem for celebrities: drug addiction.
After an arrest in 2006 for possession of prescription drugs, Michael was on a downward spiral as he found himself in handcuffs again the following year after police discovered he was under the influence when he was pulled over for blocking traffic at a red light. Michael kept the streak going in 2008 with another arrest at a public restroom where he was caught with drugs. Adding in a handful of arrests and even prison time, Michael finally entered rehab in 2010 and has avoided trouble ever since.
#6 – Bobby Brown
Former New Edition star and ex-husband to the most awarded female artist of all time – the late Whitney Houston, singer-songwriter Bobby Brown’s rap sheet long precedes him as he’s been sent to prison a total of seven times. Often making headlines for his strange and obscene (often drug-related) behavior, Brown’s arrests and charges are just as odd with one of his citations coming from a tour performance when he simulated lewd acts with audience members.
As his career and fame grew thanks to hits like “My Prerogative,” Brown’s arrests became even more frightening as he was busted on multiple occasions for driving under the influence and for possession of drugs like crack cocaine. In 2003, Brown was also sent to jail for assaulting Houston during an altercation. With additional DUI charges and stints in rehab leading up to his last arrest in 2013, Brown spent nine hours in jail before being sentenced to an 18-month alcohol program that has managed to keep this celeb out of trouble for now.
#5 – James Brown
Better known as the “Father of Funk” and the “Godfather of Soul,” James Brown makes the top five on our list with eight visits to jail. Brown’s first charge came in 1978 and wasn’t too terrible since he was only arrested for not turning over records for a radio station that was going bankrupt. The rest of his charges, however, would be much worse including everything from drugs to weapon charges in 1988, one of which led to a high speed police chase.
Sadly, Brown started using PCP in the late 1980s which led to many of his legal problems. While under the influence of PCP, he was arrested for domestic violence on multiple occasions for assaulting his wife using everything from his hands to a lead pipe. By 2004, Brown was on a path of no return with yet another domestic violence charge, which would end up being his last before his death on Christmas Day in 2006.
#4 – Snoop Dogg
As a rapper who flaunts his love of marijuana, it’s no surprise that Snoop Dogg also joins our top five with eight arrests. Long before he was famous as Snoop, Calvin Cordozar Broadus, Jr. was well on his way to a life of crime when he was arrested as a teen for possession of cocaine. Spending the majority of the 1990s in and out of prison while launching his music career, Snoop’s first arrest as a music icon came when police found a gun in his vehicle, a case that took four years to sort out.
Not surprisingly, most of Snoop’s career arrests have involved marijuana possession including a situation before an appearance on The Tonight Show with Jay Leno when he was found with weed, a firearm and cocaine. His oddest arrest, however, came in April 2006 when he and his friends vandalized a duty-free shop and injured seven police officers after being denied entry into first class in a London airport. Though initially banned from the country, Snoop has since been allowed back into the UK while many other countries refuse to lift their Snoop Ban.
#3 – DMX
Making a giant leap from Snoop’s eight arrests, rapper and actor DMX comes in at number three on our list with 13 total arrests. So where exactly should we start? Born as Earl Simons in 1970, the New York native has faced everything from weapons charges in the late 1990s to animal cruelty, identity falsification and drug possession, all of which have landed him in jail on more than one occasion. By the new millennium, things didn’t look any better as DMX’s legal battles continued to get worse.
One of DMX’s biggest arrests came in 2004 when he was under the influence and in possession of a firearm after attempting to steal a car at the airport in New York while pretending to be a federal agent. Since then, DMX has violated what seems like a perpetual probation with charges for resisting arrest, driving under the influence and possession of drugs with the intent to sell. As of December 2015, drugs were only part of his concern after failing to pay $400,000 in child support led to six months in jail and a standing warrant out for his arrest.
#2 – Mike Tyson
Praised as one of the best boxers over the last 30 years, “Iron Mike” Tyson has had dozens of memorable knockouts in the ring but he’s had even more arrests. By the time Tyson was a teenager, he had already been arrested nearly 40 times for petty crimes and fighting as people often made fun of his lisp and high-pitched voice. Though it’s hard to tell just how long Tyson’s rap sheet is, it’s undeniable that his most public arrest came in 1991 at the height of his boxing career when he was charged with rape in Indianapolis.
Serving three years of his six-year sentence, Tyson spent the rest of the 1990s on probation but not even time in prison could change his ways as his addiction to cocaine spiraled out of control. With additional arrests for driving under the influence and possession bringing his total anywhere between 30 and 50 arrests, Tyson managed to turn his life around in 2011 when he announced his sobriety and plans to live a better and healthier life. As of 2015, Tyson says he is still sober and healthier than ever.
#1 – Martin Sheen
Easily the most surprising name on our list who just so happens to take the top spot is Golden Globe and Emmy award winner Martin Sheen with a shocking total of 66 arrests. Proudly admitting to each and every arrest, Sheen’s rap sheet is as long as his list of film credits and beats out even his son Charlie’s antics thanks to spending the majority of his adult life as a human rights activist unafraid of taking a stand – legal or not.
With his arrests stemming from trespassing, civil disobedience and disturbing the peace while protesting, the 75-year-old Sheen sees his rap sheet as a laughing matter. In fact, Sheen was last arrested in 2007 when he protested at a bomb testing site in Nevada with 39 others who were taken into police custody. Though he hasn’t served extensive jail time, it’s quite comical that the Hollywood legend has more time in handcuffs than Snoop Dogg and DMX combined!