1. Justin Bieber – DUI
Canadian-born Justin Bieber has had a number of run-ins with the law over the past few years. When he was arrested on DUI suspicion in Miami, almost a quarter of a million people petitioned the White House for his deportation.
2. Robert Downey Jr. -Violated Probation
The Sherlock Holmes and Iron Man actor is among A-list royalty, but his journey to the top was rocky to say the least. After achieving Hollywood fame as a young heartthrob, Robert Downey Jr. had a widely known struggle with substance abuse throughout the 1990s. When he violated his probation following a string of criminal incidents, Downey’s laundry list of a rap sheet finally caught up with him.
3. Nicole Richie – DUI
Nicole Richie is known as the funny, fashionable mom to two adorable kids with singer Joel Madden. But the television personality used to live in the fast lane, accumulating a number of blemishes on her record during her hard-partying days. While high on various substances in 2006, Richie drove her Mercedes the wrong way on an exit ramp, entering a California highway to the dismay of other motorists.
4. Dustin Diamond – Stabbing
Dustin Diamond, the child actor who played king of the nerds “Screech” Powers on Saved by the Bell, had allegedly stabbed a man. Luckily, the man wasn’t seriously hurt despite being speared when Diamond brandished a switchblade during their brawl. In court, Screech was found not guilty of some of the heftier charges related to the incident. Still, he was convicted of two misdemeanors and served four months in jail.
5. Phil Spector – Murder
The legendary American record producer helped forge the careers and sounds of many famous girl groups during the 1960s. At the height of his work in the industry, Phil Spector even worked alongside John Lennon, Leonard Cohen, and the Ramones. Although he later faded from the spotlight, Phil found a different kind of fame in 2003. Spector killed actress Lana Clarkson in his California home, shooting her dead when she presumably failed to reciprocate his romantic advances. During the high-profile trial, other women testified about Phil’s violent behavior in their own similar experiences. The murderous music mogul is now spending the rest of his life rotting behind bars.
6. Lauryn Hill – Tax Evasion
The Fugees singer found incredible musical success throughout the 1990s and 2000s as she embarked on her solo career. But Lauryn Hill later retreated from the Hollywood spotlight, living a life of “modesty” while skipping out on tax payments for nearly $1.8 million in income.
7. Kiefer Sutherland – DUI
24 star Kiefer Sutherland has racked up an astounding four drinking and driving violations, making him one of Hollywood’s most dangerous drivers. In 2007, Kiefer failed a field sobriety test after being pulled over by police in Los Angeles. Racking up his fourth offense dating back to 1989, Jack Bauer was given 48 days in jail, and he did his time with no contest.
8. O.J. Simpson – Murder and Kidnapping
O.J. Simpson was the focus of America’s most notorious celebrity court case. In 1994, the football player’s ex-wife Nicole Brown Simpson and her friend Ron Goldman were found stabbed to death outside her Brentwood, California home. In a controversial decision, O.J. was acquitted of their murders after a high profile 8-month trial. Despite overwhelming evidence pointing toward O.J’s guilt, he managed to avoid conviction for the grisly murder. In a fitting twist of fate, Simpson was sentenced to 33 years in prison for an unrelated kidnapping at gunpoint in 2007.
9. Teresa and Joe Giudice – Fraud
The flashy stars of The Real Housewives of New Jersey made tabloid and news headlines when they were charged with making false statements to the government on a number of issues related to their finances. The table-flipping reality star and her husband pled guilty to 41 counts of fraud, and the court decided to let them serve their time separately for the sake of their four young children. The famous couple will have to repay $414,000 for failing to report tax income for the years between 2004 and 2008.
10. Mark Wahlberg – Attempted Murder
Hollywood bad boy Mark Wahlberg cleaned up his image in recent years, but the talented actor has a checkered past. As a teen growing up in Boston, Mark was arrested repeatedly for various criminal mischief. Among his worst offenses was a racially motivated incident in which the Ted star beat a defenseless Vietnamese man. Boston police charged him with attempted murder, and the future Marky Mark spent 45 days in a correctional facility. As of today, the respected entertainer still carries the crime on his permanent record.
11. Tommy Lee – Domestic Abuse
The wild drummer of Mötley Crüe fame is best known for his tumultuous relationship with actress Pamela Anderson. For most of the 1990s, stories of their numerous make ups and break ups stole tabloid headlines. But in 1998, things reached a violent head when Tommy Lee kicked Pam while she held their infant son. Tommy received six months of jail time, eventually serving four. The drummer was also ordered to attend counseling and contribute funds to a battered women’s shelter.
12. Lil’ Kim
The hip-hop queen made a very big mistake back in 2005, costing her a hefty fine and nearly a year in prison. Kim was convicted on perjury and conspiracy charges related to an incident in which a shootout occurred outside a Manhattan radio station. She falsely testified to a federal grand jury to protect her friends, and the court came down hard on the dishonest diva. She was released early, having completed ten months in a Philadelphia slammer.
13. Mike Tyson – Rape
Back in 1991, Mike Tyson was tried and convicted of rape for his sexual assault of Desiree Washington, a young pageant queen who he invited to a hotel room. Although the undisputed boxing champ claims their relationship was consensual, witnesses report Washington was shocked and disheveled after escaping from Tyson that night. A jury found Iron Mike guilty of rape, and he eventually served three years in an Indiana correctional facility. He overcame his criminal past and returned to the ring, but Tyson’s record is still marred by the incident.
14. Jay-Z – Stabbing
Jay Z ran into trouble back in 1999 after he stabbed a record executive over his suspected bootlegging of an album. Jay’s entourage created a diversion in the club while the rapper sought violent retaliation. The victim lived to tell the tale, and Jay Z turned himself into police. He posted bail and eventually pled guilty to the lesser charge of a misdemeanor, serving three years probation.
15. Winona Ryder – Shoplifting
In one of the more bizarre celebrity criminal acts of the past twenty years, Winona Ryder made tabloid history when she entered a California Saks Fifth Avenue one fateful day in 2001. Despite her international celebrity and financial success as a Hollywood actress, Winona attempted to steal nearly $5000 worth of designer goods before security apprehended her. Upon her arrest, she was charged with illegal possession of narcotics in addition to grand theft. Shocking surveillance videos showed Ryder removing the price tags from items and stuffing them in her bag. After a high-profile trial, the Little Women actress was ordered to pay restitution, fines, attend drug counseling, and perform community service.
16. Wesley Snipes – Tax Evasion
The Blade actor has enjoyed a lucrative 30-year career in the film industry. But in 2008, the truth about Wesley Snipes’ financial problems came to light. In 2010, the actor did almost three years of hard time, and upon early release, he served a brief sentence of house arrest.
17. Matthew Broderick – Vehicular Manslaughter
Matthew Broderick and then-girlfriend Jennifer Grey were visiting Ireland in 1987 when the unexpected occurred. The Ferris Bueller star was driving a rental car when the couple smashed violently into an oncoming vehicle. Broderick endured a concussion, collapsed lung, fractured ribs, and other serious injuries, while Grey sustained whiplash. Tragically, Matthew learned he had steered his BMW into the wrong lane, instantly killing an Irish woman and her daughter. He was fined $175 but released on a mere dangerous driving offense.
18. Martha Stewart – Insider Trading
Lifestyle mogul Martha Stewart built an empire founded on her prim and proper image, but the quest for money can corrupt even the most respectable individuals. In 2003, Stewart was indicted on fraud and obstruction charges when investigations revealed she had illegally sold stock based on insider information. The government came down hard on Martha, sending her away for five months in a West Virginia correctional facility. The white collar criminal learned her lesson, continued her punishment with at-home confinement, and soon returned to the spotlight in her very own television talk show.
19. Vince Neil – Vehicular Manslaughter
Back in 1984, Vince Neil was doing some hard partying at his home in California. With a blood-alcohol level over the legal limit, the Mötley Crüe frontman hopped in his sports car with fellow musician and friend Razzle, a British glam rock star. On their way to the liquor store, things took a deadly turn. Razzle was killed, and two others were seriously injured when Vince lost control of the vehicle and smashed into an oncoming car. The 80s rocker spent only a few weeks in jail, and he was sentenced to community service, probation, and restitution fees of over 2 million dollars. In the late 2000s, Neil had at least two more DUI incidents.
20. Tim Allen – Drug Trafficking
The squeaky clean actor seemed the consummate family man, lending his talents in kid-friendly movies like The Santa Clause and Toy Story. But back in 1978, Allen was pursuing a quite different career. In Kalamazoo, Michigan, Tim was busted at the airport for attempting to transport 650 grams of cocaine, a crime that could have landed him life imprisonment. Allen only served a little over two years, turning in the names of fellow traffickers. The shocking crime didn’t stop the funnyman from making it big in Hollywood!