MomSkoop
Fame and fortune can disappear in an instant when the law gets involved. Some of Hollywood’s brightest stars have watched their careers crumble after facing serious legal problems. From arrests to convictions, these celebrities learned the hard way that breaking the law comes with consequences that can last a lifetime.
1. Lindsay Lohan
Remember when Lindsay was the next big thing in Hollywood? Her talent shone brightly in movies like Mean Girls and Freaky Friday. But by the mid-2000s, everything started falling apart.
Multiple DUI arrests and trips to rehab made headlines constantly. Movie studios stopped calling because they couldn’t rely on her to show up. What should have been her prime years turned into a series of courtroom appearances instead.
2. Mel Gibson
Gibson was one of Hollywood’s biggest action stars and respected directors. His movies earned billions and won Academy Awards. Then came the DUI arrest in 2006 that changed everything.
During the arrest, he made offensive remarks that shocked the public. More controversies followed, including recorded phone calls that damaged his reputation further. Studios distanced themselves quickly, and major roles dried up.
He spent years in professional exile. Though he’s made some comeback attempts, his career never returned to its former glory.
3. Robert Downey Jr.
Before becoming Iron Man, Downey faced a very dark period. Drug-related arrests throughout the 1990s landed him in prison and rehab multiple times. His talent was undeniable, but nobody wanted to hire someone they couldn’t trust.
Insurance companies refused to cover him for films. Directors who loved his work couldn’t cast him because of the risk. His career was essentially frozen for years.
Unlike many on this list, he managed an incredible comeback. His Iron Man role launched him back to superstardom, proving redemption is possible.
4. Winona Ryder
Winona was America’s sweetheart in the 1990s, starring in beloved films like Edward Scissorhands and Little Women. Then came the shocking 2001 shoplifting arrest at a Beverly Hills department store. Security caught her stealing thousands of dollars’ worth of merchandise.
The trial became a media circus. Her wholesome image crumbled under intense public scrutiny. Movie offers slowed dramatically during what should have been her career peak.
She eventually returned to acting years later. Stranger Things helped revive her career, but she lost crucial years in between.
5. Martha Stewart
Stewart built an empire on perfection and good living. Her brand represented trust and quality in everything from cooking to home decoration. But insider trading charges in 2004 threatened to destroy it all.
She was convicted and served five months in federal prison. Her television shows went on hiatus, and some business partnerships ended. The woman who taught America how to live well was now a convicted felon.
Remarkably, she bounced back after her release. Her empire survived, though the scandal left permanent marks on her reputation.
6. Charlie Sheen
At his peak, Sheen was television’s highest-paid actor on Two and a Half Men. He earned nearly two million dollars per episode. Then his personal life spiraled completely out of control.
Legal battles, substance abuse issues, and bizarre public rants became constant news. His erratic behavior included claiming he had tiger blood and winning. CBS finally fired him in 2011, ending his golden goose.
His reputation never recovered from the meltdown. While he attempted other projects, nothing matched his previous success or paycheck.
7. O.J. Simpson
Simpson had everything: NFL legend status, acting roles, and lucrative endorsement deals. The 1994 murder charges changed his life forever. Even though he was acquitted, the trial destroyed his public image completely.
Nobody wanted to associate with him after the verdict. Movie roles vanished, and endorsement deals disappeared overnight. He became one of the most controversial figures in American history.
Later legal troubles only made things worse. His legacy shifted from football hero to infamous defendant, erasing decades of athletic achievements.
8. Felicity Huffman
Huffman was a respected Emmy-winning actress with a solid career. Her role in Desperate Housewives made her a household name. But in 2019, she got caught in the massive college admissions scandal.
She admitted to paying money to boost her daughter’s SAT scores. The public was shocked that someone so successful would cheat the system. She served 11 days in prison and faced intense criticism.
Her acting career went silent immediately. Projects were canceled, and her reputation took a serious hit that’s still healing today.
9. Wesley Snipes
Snipes was an action movie powerhouse in the 1990s and early 2000s. The Blade trilogy made him a superhero before it was cool. Tax evasion charges in 2008 brought everything crashing down.
He was convicted of failing to file tax returns and sentenced to three years in prison. His action-star momentum stopped completely during his incarceration. By the time he was released, younger actors had taken his place.
10. Mike Tyson
Iron Mike was the youngest heavyweight champion ever and one of boxing’s most feared fighters. His 1992 rape conviction shocked the sports world. He served three years in prison, missing his athletic prime.
When he returned to boxing, he was never quite the same fighter. Legal problems continued, including the infamous ear-biting incident. His reputation suffered permanent damage beyond repair.
Though he’s found new fame in recent years through entertainment, his boxing legacy remains forever tainted by his criminal record.
11. Shia LaBeouf
LaBeouf started as a Disney kid and grew into a Transformers franchise star. But repeated arrests for DUI, assault, and disorderly conduct created a pattern of concerning behavior. Each incident made headlines and damaged his professional reputation.
Directors became hesitant to cast him despite his obvious talent. His unpredictable behavior made him a liability on sets. Major franchises moved on without him.
He’s acknowledged his problems publicly and sought treatment. His career continues, but at a much smaller scale than it could have been.
12. Amanda Bynes
Bynes was Nickelodeon’s golden girl with perfect comic timing. Her transition to adult roles seemed promising with movies like She’s the Man. Then everything fell apart in the early 2010s.
Bizarre behavior, multiple arrests, and erratic social media posts concerned everyone. Her parents eventually placed her under conservatorship. Her acting career ended completely during what should have been her prime years.
She’s been working on her mental health and sobriety. But the career she once had is gone, leaving fans wondering what might have been.
13. Chris Brown
Brown was positioned to become the next Michael Jackson with incredible dance skills and vocal talent. His 2009 assault on then-girlfriend Rihanna changed everything instantly. The photos shocked the world and created massive public backlash.
Major endorsement deals vanished overnight. Radio stations reduced his airplay significantly. While he maintained some fan support, many industry doors closed permanently.
He’s continued making music, but his career trajectory changed forever.
14. Tim Allen
Before becoming a sitcom star, Allen faced serious drug trafficking charges in 1978. He was caught at an airport with over a pound of cocaine. He cooperated with authorities and served just over two years in federal prison.
His career hadn’t started yet, so the conviction delayed his entry into entertainment. He had to rebuild his life from scratch after his release. Eventually, he found success in comedy clubs.
15. Roseanne Barr
Barr was a groundbreaking comedian who revolutionized television with her working-class sitcom. Her show’s successful reboot in 2018 proved she still had drawing power. Then came the racist tweet that ended everything.
ABC canceled her show within hours of the offensive post. Cast members distanced themselves immediately. Years of work disappeared because of one social media moment.
She’s remained controversial with continued problematic statements. Her career effectively ended at the height of her comeback, proving that some mistakes are too big to overcome.