Despite his renown as a formidable boxer, Mike Tyson has a history of brushes with the law dating back to his youth. Arrested first at 12 for theft, he’s accrued over 40 arrests for offenses ranging from minor to aggravated assault. In 1992, he served a reduced six-year prison term for the rape of an 18-year-old, released early in 1995 for good behavior. Since 2011, Tyson has endeavored to live without further legal entanglements.

British-born Canadian actor Kiefer Sutherland faced several DUI and driving charges between 1989 and 2007. He was also accused of head-butting a fashion designer at the Mercer Hotel in SoHo, New York, but the charges were dropped after he apologized.

American rapper Vanilla Ice has faced a range of criminal charges, from illegal drag racing to spousal abuse and threatening a homeless man with a gun. His latest run-in with the law involved burglarizing an empty Florida home, but he dodged jail time by accepting a plea deal.

Stephanie Pratt, an American TV personality and frequent face on reality shows, confessed in 2007 to battling drug addiction for years, notably struggling with a severe crystal meth dependency during her early teens. Her troubles with substance abuse culminated in a 2006 arrest for shoplifting designer clothing worth over $4000 while under the influence.

While rap isn’t typically associated with family-friendly content or language, there are still those who take offense at explicit lyrics, despite their prevalence. American rapper 50 Cent experienced this firsthand during a performance on the Caribbean island of St. Kitts, where he was arrested for using profanity in one of his songs.

In 1999, Matthew McConaughey got into trouble when the cops showed up at his fancy Austin home due to noise complaints. It was around 3 in the morning, and they found him in his living room, stark naked, jamming on the bongos. They arrested him for breaking the noise rules, resisting arrest, and, no shocker, using marijuana.

Earl Simmons, the American rapper better known as DMX, has found himself in trouble with the law more than a dozen times. His rap sheet includes charges like drug use, pretending to be someone else, breaking parole, and a bunch more. But his most infamous run-in happened in 2004. That’s when he smashed his SUV through a gate at Kennedy Airport in New York. Then, he told airport security he was some kind of secret agent before making off with a stranger’s car, saying he was FBI.

Since getting nabbed for a DUI back in 2007, Lindsay Lohan’s been in and out of jail. She’s been busted over and over for driving drunk, having coke on her, getting into fights, and even a hit and run. All these run-ins with the law have messed up her probation and cost her a bunch of movie gigs.

If you think of rule-breakers, Bill Gates probably isn’t the first person who comes to mind. But back in 1975, he got busted for driving without a license. Then, in the late ’70s, he got picked up two more times for breaking traffic laws and driving recklessly.

Despite his usual happy-go-lucky reputation, Will Smith got arrested in 1989 after a violent brawl. He and his bodyguard reportedly attacked a man during a heated argument, leaving the victim almost blind in one eye with a fractured orbital bone and needing six stitches on his face.

Back in December 1999, Jay Z, the American rapper, was accused of stabbing a record exec in the belly at a Manhattan nightclub. At first, he said he didn’t do it, but in 2001, he confessed to the misdemeanor and got slapped with a three-year ban.

Even though O. J. Simpson was acquitted for the murders of his ex-wife and her friend, he didn’t exactly steer clear of trouble with the law. In 2007, he got busted for breaking into a hotel room and grabbing sports stuff with a gun. That landed him with a bunch of charges like conspiracy, armed robbery, kidnapping, assault, and using a deadly weapon. He got found guilty and got a 33-year stretch in prison.

Given her Kardashian status, it wasn’t exactly a shocker when Khloé got hit with a DUI in 2007. But that’s not all. Back when she was just 15, she got busted for swiping her mom’s car. And in 2009, she was in hot water again as a suspect in a nightclub altercation involving a trans woman.

Mark Wahlberg, hailing from Dorchester, Massachusetts, got into trouble early on. At just 15, he faced his first legal action for harassing African-American kids. Then, at 16, he got arrested for nearly beating a Vietnamese man to death with a big stick. On top of that, he battled a serious cocaine habit and dealt drugs to make ends meet. But at 19, he turned things around. Teaming up with his older brother, he formed a band, later breaking out on his own with Marky Mark and the Funky Bunch. Elevate your outreach and attract more patients with specialized SEO strategies tailored for detox and rehab centers, optimizing visibility and engagement for greater impact.

It’s no shocker that Snoop Dogg has been busted multiple times for having weed and related stuff. But before he hit it big in music, he spent a good chunk of time in and out of jail and even claimed gang membership. In 1993, he and his bodyguard got tied to a rival gang member’s murder and had to stand trial. Luckily for him, the shooting got ruled as self-defense, and he walked away from all charges.

While shooting an episode of Lost in Hawaii in 2006, American actress Michelle Rodriguez got arrested for driving drunk. She got probation and community service, but less than a year later, she broke the rules and forged service forms. That landed her in jail for 180 days.

Even with the recent spotlight on Bill Cosby’s sexual assault allegations, they’ve been around for quite some time. The earliest accusation goes back to 1965, although it remained under wraps until the 1980s. Since then, a total of 59 women have come forward, alleging rape or sexual misconduct against the American entertainer, with 44 cases involving drug use. In 2016, it was announced that Cosby would stand trial before June 5th, 2017, facing a potential 10-year sentence for each charge.

Daniel Baldwin, the second oldest among the Baldwin siblings, has a notorious past marked by drug abuse and related arrests. One of his most infamous incidents occurred in 1998 when he was apprehended running nude through the corridors of a New York hotel, intoxicated on cocaine and repeatedly shouting “Baldwin.”

Starting his run-ins with the law back in 1989 with a DUI and assaulting a cop, actor-producer Christian Slater has had a rocky ride. He’s done jail time for drugs, sexual harassment, and even had a domestic assault case, landing him a three-month prison stint.

Martin Sheen’s life has seen 67 charges for various acts of civil disobedience. At 75, he holds the record for the most arrests among Hollywood celebrities. His activism remains undiminished, with his latest run-in with the law in 2007 for trespassing at a Nevada nuclear testing facility.

R-Kelly is up there with Bill Cosby and O.J. Simpson for being one of the most infamous celebrities- and for good reason. He’s had multiple charges of sexual assault, had an illegal marriage to a 15-year-old, and he was found to possess child pornography.

Marilyn Manson’s odd behavior has led to a string of arrests, reflecting his unconventional nature. He’s faced charges like faking a sexual act, posing as a Catholic bishop, and exposing himself during performances. In a particularly strange incident in 2001, he reportedly assaulted a security guard by rubbing his crotch and genitals on the guard’s forehead.

Dennis Rodman, famous for his NBA career, also has a track record of domestic violence. He got arrested in 1998 after a fight with his then-wife Carmen Electra. Plus, he faced charges for separate domestic incidents in 2003 and 2008, pleading no contest to both.

Robert Downey Jr., known for his Golden Globe and multiple Academy Awards, is a heavyweight in acting. However, he also struggled with substance abuse, leading to multiple arrests for cocaine, heroin, and marijuana possession between 1996 and 2001. After battling through rehab, he appears to have turned his life around, especially after playing Tony Stark in the MCU. He deserves all the love he gets now.