1. Will Smith
Back in the day when Will Smith was merely 20 years old in 1989, he, along with a group of friends attacked a record promoter and beat him senselessly, leaving him blind in one eye. Will would later be cuffed and sent to jail. Although he only had to spend one night in jail, he has called the term behind bars the worst night of his life several times in interviews.
2. Mickey Rourke
Mickey Rourke found himself in hot waters when he physically abused his then-wife, Carre Otis in 1994. Although he was arrested for his heinous actions, all charges were dropped against him later. Rourke did claim the accusations were not true and that the troubles in their marriage were used by Otis’ agent to further her career. Whether the rumors are true or not, we wouldn’t want to be on Mickey’s wrong side.
3. Tim Allen
Before showcasing his comedic presence on the screen, Tim Allen was a mess. He had financial problems and he would often sell drugs to make bill payments. One day in 1978, he got unlucky and the law enforcers caught him and arrested him for the possession of 1.4 lb cocaine. He initially got a sentence of 3 to 7 years but was released early for cooperating with the officials. Tim had to stay 2 years and 4 months behind bars; he was located in a Minnesotan correctional facility.
4. Danny Trejo
Danny Trejo has had numerous run-ins with the law enforcers. He has spent a collective 11 years in correctional facilities because of crimes such as robbery and drug abuse. People in Hollywood are well aware of his stint in the California prison system for several years. His shady back story hasn’t prevented him from starring in several movies such as Con Air, Heat, Desperado and Machete, etc.
5. C-Murder
C-Murder was living the life of a successful rapper before his sentencing. In fact, he had released nine albums before being convicted of second-degree murder. He was ostensibly involved in an altercation in 2001, and the tussle provoked him into pulling the trigger on the owner and the bouncer of a night club. If reports are to be believed, C-Murder fired shots after being denied entrance to the club for the possession of arms.
6. Shelley Mail
Currently, Shelley Malil spends his life rotting away at Ironwood State Prison in Riverside County, California. Shelley wasn’t exactly going anywhere with his acting career managing notable roles in only The 40-year-old virgin, Holes, Collateral Damage, and Columbus Day, etc. He was apprehended at an Amtrak station for stabbing his ex-girlfriend 23 times and was, thus, sentenced to life in prison on December 16, 2010.
7. Phil Spector
Phil Spector has worked with the likes of John Lennon, Leonard Cohen, George Harrison, and the Ramones in the past as a record producer. In 2000, Phil underwent two trials for murder and second-degree murder. He was convicted of second-degree murder in 2009 and was, thus, sentenced to 19 years in the confined bars of a prison. He was charged for playing an atrocious role in the murder of Lana Clarkson.
8. OJ Simpson
OJ Simpson rose to prominence playing professional football as a running back for the NFL teams, the Buffalo Bills and the San Francisco 49 ers. The man faced the wrath of the court when he was ordered to pay a whopping $33.5 million in damages for the wrongful death of Brown and Goldman. He would have another run-in with the law enforcers; he was also apprehended for stealing sports memorabilia. It led him to face a jail sentencing of 33 years.
9. Don King
Synonymous with boxing promotions, Don King failed to act in accordance with the law in 1966 when he stomped Sam Garrett to death. The heinous crime only landed him 3-and-a-half years in prison after his charges were reduced to manslaughter; he was originally on trial for second-degree murder. The boxing promoter’s biggest career highlight to this day remains to spearhead the promotions of “The Rumble in the Jungle,” and the “Thrilla in Manila.” He also went on to promote some of the biggest names in boxing such as Muhammad Ali, Mike Tyson, Evander Holyfield, Joe Frazier, and George Foreman, etc.
10. James Lipton
James Lipton came into the limelight as the executive producer, host, and writer of the series, Inside the Actors Studio. Before becoming all high and mighty, he made ends meet as a pimp in Paris, France. He got into the prostitution ring after befriending a prostitute there. He has been quoted saying, “The French mecs didn’t exploit women. They represented them, like agents. And they took a cut. That’s how I lived. I was going through my rites of passage, no question about it. It was a great year of my life.”
11. Christian Slater
Christian Slater has committed many crimes over the years. In 1989, he was charged with drunk driving and assault. In 1994, he tried to board a commercial airline with a loaded gun in his luggage. He would later assault his then-girlfriend, Michelle Jonas, and a police officer in the same year. Christian faced the wrath of the law enforcers again in 2005 when he was apprehended for sexually assaulting a woman on the street.
12. Amy Locane
In February 2013, Amy Locane was handed a three-year term in prison after being convicted of vehicular manslaughter. She had crashed her car, in turn, killing a 60-year-old woman and severely injuring her husband a few years back in 2010. When tested, it was identified that her blood alcohol was at least 3 times the legal limit for impairment. The actress was given fairly lenient sentencing as the judge took Amy’s two young daughters, one of whom has Crohn’s Disease, into consideration.
13. Laura Bush
Former first lady, Laura Bush, committed a heinous crime back in November 1963 when she ran a stop sign and collided with another car. The accident led to the death of 17-year-old, Michael Dutton Douglas. Laura Bush came out of the accident with minor injuries. Reflecting back on the incident, Laura Bush has said, “It was a very tragic accident that deeply affected the families and was very painful for all involved, including the community at large.”
14. Vince Neil
Vince Neil, the frontman of Motley Crue, caused the death of his friend Nicolas Dingley when he lost control of the car they were driving in and hit an oncoming vehicle. The crash led to the demise of his friend Dingley who was seated in the passenger’s seat. Neil was later charged with vehicular manslaughter and driving under the influence of alcohol. Neil served half of a 30-day jail sentence, received five years probation and had to pay $2.6 million in restitution, as well as perform 200 hours of community service.
15. Mark Wahlberg
Mark Wahlberg had several run-ins with the Boston Police Department even before reaching adulthood. However, the one crime that triumphs over the petty ones is his racially motivated attack on a middle-aged Vietnamese man when he was 16. Mark knocked the man unconscious in the middle of the street with a wooden stick. Later in the day, Mark went on a rampage again and attacked a different Vietnamese man blinding him in one eye. Mark had to spend 45 days behind bars; he was initially sentenced to two years in prison.
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