For one reason or another, everyone loves a bad boy. Hollywood is no exception. There are countless Hollywood bad boys, but they’re only playing characters. It’s one thing to play a drug trafficker onscreen, and it’s another to be arrested for drug trafficking. Amazingly, Hollywood doesn’t seem to know the difference. When reading through this list, you’ll see how your favorite celebrities — even your favorite family-friendly rapper, TV dad, or action stars — once lived outside the law.
The celebrities on this list turned to a life of crime for different reasons. Some were struggling to make a living, some lost their temper, and others were just a product of their environment. That doesn’t excuse their behavior. But, for the most part, the people found on this list have put their past behind them. And so has Hollywood. Despite the incredibly shady pasts of these actors, musicians, and athletes, Hollywood continues to love them. Considering how fast Hollywood was willing to forget the terrible actions of these celebrities, it really says something about the entertainment industry. Seriously, how does a convicted rapist launch an entertainment career?
15. Will Smith — Aggravated Assault
Everyone’s love of Will Smith started when he starred in The Fresh Prince of Bel-Air. Sure, he was everyone’s favorite family-friendly rapper in the early 1990s, but he transitioned to an acting career seamlessly. Today, he’s one of Hollywood’s favorite stars — but he’s had a shaky history. When his rhymes were family friendly, his behavior was not.
According to numerous reports, Will Smith was arrested when he was 20 years old after an argument with a man escalated rather abruptly. After winning the first-ever rap Grammy, Will Smith allegedly ordered his bodyguard Charles Alston to attack a record promoter named William Hendricks. The assault was so aggressive that Hendricks needed six stitches and almost lost sight in his eye.
A source close to Will Smith said, “Will had to spend a night in the cell at West Philadelphia police station with other inmates waking him up all night long asking for his autograph. It was the worst night of his life. He wants to forget it ever happened.”
14. Caitlyn Jenner — Vehicular Manslaughter
Caitlyn Jenner has been the subject of global media attention after her family became reality-television stars. She became a controversial figure after coming out as transgender and choosing to live her life as a woman. While this decision does take a whole lot of courage, her family was incredibly supportive of her decision. In fact, most people were supportive of her decision, so much so that she won Woman of the Year in 2015, which angered a number of the previous winners of the award.
In that same year, Jenner was involved in a car crash that resulted in the death of a 69-year-old woman. Video of the event, where it seemed that Jenner was very clearly at fault, was leaked to the public. Born a man, Jenner could’ve been sent to a male prison if she was convicted of the vehicular manslaughter charge. But if a Kardashian could get O.J. Simpson to avoid prison time in a highly publicized murder trial, there was almost no chance Jenner was going to be sent to prison.
13. Samuel L. Jackson — Held Martin Luther King Sr Hostage
Samuel L. Jackson has always been one tough motherf****r. Appearing as a certified badass in over 100 films, Jackson was asked if his likeness could be used to create an Ultimate version of Nick Fury, whom he appears as in the Marvel Cinematic Universe. He’s a household name now because of his extensive filmography. But when he was a young man, Jackson spent more time focusing on civil rights than his acting career.
Samuel L. Jackson attended the funeral of Martin Luther King Jr. as one of the ushers in Atlanta. A year following the assassination, Jackson and a number of associates held members of the Morehouse College board of trustees hostage on campus. One of the men that Jackson held hostage was none other than Martin Luther King Sr. The aim of the hostage situation was to demand reform in the school’s curriculum and governance.
While his demands were met, Jackson was eventually charged and convicted of unlawful confinement. He was suspended from college for two years and joined the Black Power movement during this time. He said that he felt empowered when Black Power began buying guns. His mother forced him to move to Los Angeles after she was informed by the FBI that Jackson would be dead within a year if he remained a member of Black Power!
12. Mark Wahlberg — Attempted Murder
Recently, Mark Wahlberg overtook Dwayne “The Rock” Johnson as Hollywood’s highest-paid actor. According to reports, Wahlberg has pulled in over $68 million in the past 12 months. His massive paycheck can be attributed to his roles in Transformers: The Last Knight and Deepwater Horizon. But, as many may remember, Marky Mark was not always Hollywood’s favorite action star.
At the age of 16, Wahlberg bashed a middle-aged Vietnamese man named Thanh Lam on the street with a wooden stick. Wahlberg beat the man unconscious, calling him a number of racial slurs that referenced the man’s Vietnamese heritage. That same day, Wahlberg sucker-punched another Vietnamese Man, Hoa “Johnny” Trinh. Both attacks were completely unprovoked.
Wahlberg returned to the scene of the first crime and seemed to boast about what he had done to the man. He told police officers, “You don’t have to let him identify me, I’ll tell you now that’s the motherf****r whose head I split open.”
Wahlberg was charged with attempted murder, pleaded guilty to assault, and served 45 days of a two-year sentence in prison. Five years later, Wahlberg attacked another man for no reason, fracturing the man’s jaw.
11. Matthew McConaughey — Drug Possession
One of Hollywood’s most famous actors, McConaughey is known for one of his first lines on screen: “alright alright alright” in Dazed and Confused (1993). Though he’s had thousands of lines since then, he is (and will always be) associated with that phrase. In fact, if you mention his name, the first words most movie fans will say is “alright alright alright.” While he’s living the high life now, McConaughey has had a rather troubling history with the law.
While it’s not uncommon for celebrities to be arrested for drug-related crimes, McConaughey was arrested just as he was starting to make a name for himself in Hollywood. In 1999, McConaughey was arrested at his Texas home when he was spotted playing the bongos naked while dancing with another man who was clapping along. He was charged with suspected possession of marijuana and resisting transportation after he ignored the officer’s request to put pants on.
10. Woody Harrelson — Disorderly Conduct & Resisting Arrest
It didn’t take Woody Harrelson very long to become one of the most loved actors in Hollywood. Whether you love him for his serious performances or for goofing around onscreen, Harrelson is one of the most favored actors in the industry. But, he isn’t as well behaved as his public persona would have you believe.
In 1982, Harrelson was arrested for disorderly conduct while dancing in the middle of the street. He ran from police, adding a charge of resisting arrest charge to his rap sheet. In 1996, Harrelson was arrested for planting hemp seeds to challenge state law, which didn’t distinguish between hemp and marijuana. In 2002, Harrelson was arrested in London after acting aggressively in a cab. Breaking the door of a cab, Harrelson ran and tried to escape into another cab. The first cab followed the second before getting the police involved, which is when Harrelson tried to escape on foot. For the ordeal, Harrelson spent the night in jail.
9. Matthew Broderick — Careless Driving Resulting in Death
A year after starring in Ferris Bueller’s Day Off (1986), Matthew Broderick was arrested and charged with reckless driving resulting in death. The incident occurred while Broderick was driving a rented red BMW in Northern Ireland when he crashed head-on with mother and daughter Margaret Doherty, 63, and Anna Gallagher, 28. While Broderick only suffered a broken leg, Margaret Doherty and Anna Gallagher were killed. When asked about the crash, Broderick said, “I don’t remember the day. I don’t remember even getting up in the morning. I don’t remember making my bed. What I first remember is waking up in the hospital with a very strange feeling going on in my leg.”
Broderick was originally looking at five years in prison, but his original charge was changed to careless driving and was fined $175, to the dismay of the victim’s’ family. The family called this ruling a “travesty of justice.” The brother of one of the victims tried to meet with Broderick years later to get closure, but his plans fell through.
In 2012, Broderick was featured in a multimillion-dollar Honda commercial, which aired during the Super Bowl. A member of the victim’s family said that Broderick, “knowing his past,” was a poor choice of a driver.
8. Tim Allen — Drug Trafficking
Tim Allen became everyone’s favorite dad when he played Tim “The Toolman” Taylor in Home Improvement (1991-1999). Throughout his career, Allen has found himself in a number of family-favorite roles. He played Santa Claus in The Santa Claus trilogy and voiced the iconic Buzz Lightyear in the Toy Story franchise. Recently, Allen starred in Last Man Standing (2011-2017), trying to become an iconic television dad once more. But as you may have heard, Tim Allen wasn’t always a family man.
In 1978, while struggling to make a career out of being a comedian, Tim Allen was arrested at Kalamazoo International Airport for possession of 650 grams (1.43 lbs of cocaine). In order to avoid life in prison, Allen struck a deal with the prosecution and agreed to snitch on his colleagues. Allen was sentenced to three to seven years in prison and was released after serving two years in a federal prison.
7. Jay-Z — Stabbed A Record Executive
To say Jay-Z had a rough upbringing is an understatement. Growing up in Brooklyn, New York, Jay-Z is one of few rappers who can actually boast about a criminal past. He wasn’t a music studio gangster; he was the real deal. As a teenager, he sold crack cocaine and was shot numerous times. While his previous crimes are often referenced in his music, there’s one crime that few people know about.
In 1999, when Jay-Z was dominating the hip-hop charts, he nearly threw his entire career away in a single night. According to reports, Jay-Z was under the belief that hip-hop producer Lance “Un” Rivera had leaked Jay-Z’s upcoming album (Vol. 3… Life and Times of S. Carter) a month early. Angry about his music being released before he intended, Jay-Z approached Rivera at a party and got physical. Rivera was treated at the hospital for a rather serious stab wound, and Jay-Z turned himself into authorities the following day. He was sentenced to three years probation.
6. Bruno Mars — Cocaine Possession
Bruno Mars has made quite the name for himself since he broke into the music scene in 2009. With a number of hit singles early in his career, it seems that every project Mars joins is a commercial success. While his talent has been criticized by artists in the past, Mars continues to do his own thing and to dominate charts around the world. His most recent album, 24K Magic (2016), was drastically different from his previous material but was met with nothing but love from fans and critics. But, like any pop star, Mars has had his share of low points in his career.
In 2010, just a year after he was signed to Atlantic Records, Bruno Mars was arrested for possession of cocaine at the Hard Rock Casino in Las Vegas. Apparently riding the success of his first number one record, Mars told police officers that he had never used drugs before (something he later admitted was a lie). Nonetheless, Mars pleaded guilty to felony drug possession and was told his record would be cleared if he wasn’t arrested at all in the next year. In addition, Mars agreed to pay a $2,000 fine and serve 200 hours of community service.
5. Chris Brown — Domestic Violence
Chris Brown was once MTV’s teenage heartthrob. When he began dating Rihanna in the late 2000s, celebrity entertainment magazines were ecstatic. The pop duo was set to be the next great Hollywood couple — but all of that changed on February 9, 2009.
After an argument between Rihanna and Brown became physical, Rihanna needed to be hospitalized due to her injuries. The wounds on Rihanna’s face were quickly published my tabloids, and everyone’s perception of Brown changed overnight. Due to everyone’s reaction to Rihanna’s injuries, Brown hired a crises management team to help change his public image after he began losing advertising deals, public performances, and airtime on radio stations.
Brown pleaded not guilty to felony assault but later changed his plea to guilty after striking a plea deal. For his actions, he was sentenced to five years probation, one year of domestic violence counseling, and six months community service. In addition, he was ordered to stay 50 yards away from Rihanna at all times, except for at public events, where he must remain 10 yards away.
When it was believed that Brown was a changed man, Hollywood loved him once more. His music career is in full stride again — despite the fact that his most recent ex-girlfriend, Karrueche Tran, was granted a 100-year restraining order against Brown. Tran claims that Brown had threatened to kill her.
4. Mike Tyson — Convicted R—–t
Once a highly respected boxer, Mike Tyson‘s life went into the gutter as his career came to an end. Over his boxing career, Tyson managed to earn $400 million. But soon after his career ended, he found himself over $38 million in debt. He spent his money on a $2 million bathtub for his wife, a $410,000 birthday party, $230,000 on cell phones, $140,000 on two white Bengal tigers, and a number of purchases that left the public shaking their heads. On top of his financial problems, Tyson faced a number of criminal charges.
In 1991, Tyson was arrested for the rape of 18-year-old Desiree Washington. While under oath, Tyson said that Washington was consenting to his sexual advances. He was sentenced to six years in prison, but only served three. On top of this charge, Tyson was arrested numerous times in 1988 for assault and battery and countless sexual harassment claims and through the 1990’s for a number of assault charges.
It’s amazing that someone with so many run-ins with the law has been able to change his public image so abruptly. It started with his appearance in The Hangover (2009) and a number of charitable appearances. He’s since been given his own animated show, Mike Tyson Mysteries (2014-present).
3. Eminem — Assault With A Dangerous Weapon
Eminem is no stranger to controversy. With so many jabs at celebrities, media companies, politicians, and even his own fans, it’s amazing that Eminem has had the illustrious career that he’s had. Though he struggled with drug use during the peak of his career, Eminem has lived a life on the straight and narrow since making his comeback in 2009. Nonetheless, we can’t forget some of the things that Eminem has done in the past.
For example, in 2000, Eminem was sentenced to two years probation for carrying a concealed weapon outside of a bar in Warren, Michigan. He was charged after pistol-whipping John Guerra, whom Eminem claimed was kissing his ex-wife, Kim. Due to his plea, the prosecution dismissed a charge of assault with a dangerous weapon. As part of his punishment, Eminem was unable to drink alcohol or take any controlled substances for two years, unless prescribed by a doctor. Is this when his addiction to prescription medication began? It’s hard to say.
While there are few criminal charges that Eminem can be pinned with, there’s no doubt that there are a number of things he’s done but didn’t get arrested for. He’s good friends with 50 Cent, after all.
2. Snoop Dogg — Murder
Snoop Dogg is one of the best-known rappers to come out of the ’90s. Like many of the rappers from this era, Snoop Dogg had a troubled life growing up. He’s admitted that for a long time, he was a member of the notorious Crips gang and would often reference them in his music. That chapter of his life was closed after Snoop Dogg was kicked out of his hometown by the local Crips when he tried to pay them a visit.
In 1993, Snoop Dogg was arrested for the murder of Philip Woldemariam. Snoop, along with his bodyguard, McKinley Lee, was charged with voluntary manslaughter after a six-day deliberation by the jury. While the prosecution argued that Snoop and his bodyguard shot a man trying to flee, it was later argued in court that Woldemariam was killed in an act of self-defense.
1. Robert Downey Jr. — Possession of Heroin & Cocaine
Robert Downey Jr. has had a roller coaster of a career. Though he’s always had talent, his career was almost ruined by his excessive drug habits in the 1990s. His drug use was so bad that despite winning a Golden Globe Award for his role in Ally McBeal, his character was written out of the show.
In 1996, Robert Downey Jr. was arrested after being found with heroin, cocaine, and a pistol in his vehicle. He was sentenced to four years probation but violated his probation and ended up in prison for six months. In 1999, after failing to meet his parole conditions, he was sentenced to three years in prison but ended up serving a little over a year.
It’s often said that addicts need to hit rock bottom before they can successfully complete treatment. For Robert Downey Jr., he hit rock bottom while eating a Burger King burger so terrible that he threw all of his drugs into the ocean and began his journey to sobriety.
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