Top 10 Celebrities Who Overcame Legal Trouble

Throughout the 1990s, Reese Witherspoon was lucky enough to be cast in a handful of projects that saw her working with some pretty big names. The release of “Legally Blonde” in 2001 put her into the spotlight. Ironically, she could have used the help of her character Elle Woods when she was involved in an incident in 2013. When her husband Jim Toth was pulled over for suspicion of driving under the influence, Reese was arrested for disobeying the orders of a police officer who instructed her to remain in the vehicle. Despite this bump in the road, Witherspoon has enjoyed a successful film and television career since then.

No one would have ever guessed the mild-mannered Woody Boyd of “Cheers” would be one to bump into the law from time to time. Woody Harrelson has had more than one clash with law enforcement over the course of his lifetime. He’s been arrested for dancing in the middle of a street and was even involved in a police chase in a taxi in London. One of the most notable incidents was when he was arrested for planting hemp seeds when the state insisted they were the same as marijuana. However, his clashes with the law have not seemed to hurt his career. One quick peek at his filmography, and it’s clear his talents are still in demand.

She’s a huge hip-hop star the world over, and she certainly isn’t one to keep her opinions to herself. Nicki Minaj has never been one to avoid spats with fellow performers, but it’s all been within the realm of banter between artists. Her fame and fortune came long after a 2003 arrest for criminal possession of a weapon with intent to use. Minaj posted, and then deleted, a copy of her mugshot on social media and seemed to brag about the incident calling it “inspiring.” The arrest must have done something, as she did go on to become a massive success.

“What the hell were you thinking?” You said it, Jay. It was 1995 and Hugh Grant was becoming quite the name around Hollywood. “Four Weddings and a Funeral” had come out the year before and he was beginning to emerge as one of Hollywood’s next leading men. Then along came Divine Brown. Grant was arrested in June of 1995 for engaging in inappropriate behavior with a working girl. The news of the incident spread like wildfire and many thought that was the end of his career. Surprisingly, though, he went on “The Tonight Show with Jay Leno” and gave a very sincere, heartfelt apology. It apparently worked, as Grant has continued to be successful to this day.

Have you ever wondered what famous people are doing in their homes when they are away from the limelight? Well, apparently if you’re Matthew McConaughey, you dance around naked playing the bongos. Matt was arrested in October of 1999 when neighbors complained about the loud music in his home. The police arrived and arrested McConaughey when they suspected he was in possession of illegal drugs in his home. The incident ended up as only a minor blip on Matt’s radar as he continued to find overwhelming success in his film projects. Most of which have him wearing pants.

In 2001, Winona Ryder was shopping at Saks Fifth Avenue in Beverly Hills, when she got caught trying to steal $5,500 worth of designer clothes. She had just come off several successes and this high profile incident had the potential to shatter her career. The arrest resulted in the loss of movie roles due to the producers’ inability to get insurance for her. She took a break for several years and re-emerged in a few independent films, which helped her return to the main fold of Hollywood. She has since gone on to star in the acclaimed Netflix series, “Stranger Things.”

It seems even the world of professional sports sees its stars take a hit from time to time. Famous golfer Tiger Woods was arrested in 2017 for driving under the influence. His car was stopped in the middle of a road while Woods himself was asleep at the wheel. He claimed he had taken a combination of prescription drugs and was unaware of how they would react together. Woods only had to pay a small fine and could not consume alcohol for one year while he was on probation. Despite the incident, Woods would later make a triumphant return, winning the 2019 Masters tournament.

It’s no secret that there’s a history of violence between rival rappers. Names like The Notorious B.I.G. or even Tupac Shakur immediately bring to mind some of the heavier threats that hip-hoppers have witnessed. Mild in comparison, rapper Jay Z found himself in an incident back in 1999 which saw him arrested for stabbing Lance “Un” Rivera. He was eventually convicted for third-degree assault and took a three-year probation sentence. It certainly didn’t hurt his reputation or his record sales, as he’s become a massive influence in hip-hop culture since then. He even went on to marry Beyonce.

The queen of the kitchen found herself in a whole lot of hot water that started in December of 2001. Accused of insider trading, Stewart dodged questions and accusations for months before she was finally indicted in June of 2003. She was found guilty of insider trading, and sentenced to five months of incarceration in Alderson, West Virginia, and also spent five months in home confinement after being released. The incident did not, however, put a dent in her career. She made a huge comeback and became even more popular than she had ever been before. Perhaps Martha really does think the entire incident was “a good thing.”

Before we unveil our top pick, here are a few honorable mentions.

Halle Berry
Leaving the Scene of a Crime

Bruno Mars
Drug Possession

Michelle Rodriguez
Multiple DUI Incidents

Tim Allen
Drug Trafficking

Paris Hilton
Served Time for Drug Possession

The late 90s and early aughts were not a good time for Robert Downey Jr. He was arrested repeatedly on drug charges, and spent almost a year in jail. It was a time when he was severely troubled and struggled greatly with addiction issues. The cycle of arrests, rehab, and relapses came to an end in late 2004. With a little help from his longtime friend Mel Gibson, Downey got a few good gigs that saw him on the path to recovery. Now when you hear the name Robert Downey Jr, the likes of “Iron Man” and the massive world of the MCU come to mind.