10 Most Infamous Celebrity Arrests

Top 10 Celebrity Arrests

Welcome to WatchMojo, and today we’re counting down our picks for the Top 10 Celebrity Arrests.

For this list, we’ll be looking at infamous times that police apprehended celebs.

Which celebrity arrest shocked you the most? Let us know below!

#10: Shia LaBeouf

The controversial actor has had several altercations with the police throughout his career. But perhaps his most famous was in 2017. In the early morning in Savannah, Georgia, an intoxicated LaBeouf, who was there to film “The Peanut Butter Falcon,” approached a stranger and a police officer to ask for a cigarette. When they didn’t give him one, he became enraged, went on a profanity-riddled rant, and refused to leave. As he was arrested, he claimed it was because he was white, and said the officer was going to hell because he was Black. The “Transformers” actor was found guilty of obstruction, fined $1,000, put on probation for a year, and had to undergo therapy for anger management and substance abuse.

#9: Lindsay Lohan

The spring and summer of 2007 was a turning point for the “Mean Girls” actor, but not in a good way. You see, that year was the first of several run-ins with the police. In May, Lohan was arrested for driving under the influence. In July, around two weeks after going to rehab, she was arrested for driving under the influence again - as well as driving with a suspended license and possession of illegal substances. In August, Lohan accepted a plea deal for misdemeanors. As part of it, she had to spend one day in prison, undergo an 18-month alcohol education program, complete ten weeks of community service, and be on probation for three years. Well, in November, Lohan spent a MASSIVE 84 minutes in prison before being released due to “overcrowding.”

#8: Martha Stewart

If you were looking for cozy TV, then “Martha Stewart Living” was the show for you. Covering cooking, gardening, and whatnot, it helped turn Stewart into a beloved figure. But in the early 2000s, news broke that the media mogul had taken part in insider trading. On the advice of a stock broker, she sold all of her shares in ImClone Systems. By 2004, she faced trial on numerous charges, including obstruction of justice and securities fraud. In the end, Stewart was found guilty of several felony offenses. She was sentenced to jail for five months and fined $30,000. Afterward, she had two years of supervised release. Stewart must have made some friends inside, as she was given the nickname “M. Diddy.”

#7: DMX

If there was an award for musicians with the most legal battles, this New York rapper would be in the running. Over the years, he’s faced charges of animal cruelty, using illegal substances, robbery, and much more. But his biggest legal clash was probably in 2017. DMX was charged with a whopping 14 counts of tax fraud, and pleaded guilty to a single count. Although prosecutors were looking for a five-year sentence, the judge took pity on the rapper and sentenced him to prison for one year. He also had to pay $2.29 million in restitution. After his release in early 2019, DMX began three years of supervised release, but passed away in 2021.

#6: Robert Downey Jr.

The story of this MCU actor, from addiction and arrests to achieving national treasure status, deserves a film of its own. Engulfed by addiction, nothing seemed to work for Downey as he had one issue after another. In 2000, he was arrested while under the influence in his hotel room in Palm Springs, California. In 2001, when out on parole, Downey was found wandering around barefooted and arrested again. While he was released, it was the final straw for the producers of “Ally McBeal”, who fired him. Downey pled no contest to the Palm Springs charges. He avoided jail but was given three years of probation and ordered to go to rehab. Downey later said this moment led to him realizing he needed help.

#5: Ezra Miller

The saga of Ezra Miller is one of the biggest ongoing scandals in Hollywood, with many accusations having come to light. And it all started with an arrest in Hawaii. In March 2022, Miller was at a karaoke bar. They apparently became enraged when other patrons were singing and began insulting them. Miller also lunged at someone playing darts. The cops arrested Miller for harassment and disorderly conduct. Then, in April, Miller attended a house party in the same state. When asked to leave, they angrily responded by throwing a chair at a woman’s head, leaving a cut on her forehead. Miller was arrested for assault. They pled no contest to the karaoke bar charges and were fined $500.

#4: Michael Jackson

Considered one of the best pop performers of all time, the former Jackson Five member had a murky personal life filled with rumors and accusations. After the 2003 documentary “Living with Michael Jackson” was released, the authorities began investigating the “Thriller” singer. Facing charges like child abuse and extortion, Jackson went to trial in 2005. With the world watching closely, the court case lasted a long four months. Much of the media’s coverage was criticized for portraying Jackson as already guilty. In June, he was found not guilty of all charges. However, new accusations after his death in 2009 have continued to raise questions about his life and legacy.

#3: R. Kelly

While the R&B singer was long celebrated for his music, he’s faced accusations of sexual misconduct since the 1990s. Despite numerous civil suits and criminal trials, it wasn’t until 2019 that Kelly began to face real consequences. Shortly after the release of the documentary series “Surviving R. Kelly,” the singer was charged with 10 counts of aggravated criminal sexual abuse in Illinois. While out on bail a few months later, he was arrested on federal charges for multiple sex crimes and obstruction of justice. In June 2022, he was found guilty on nine counts and sentenced to 30 years in prison. In September, Kelly was also found guilty in Illinois of six out of thirteen charges against him.

#2: O. J. Simpson

In June 1994, Americans were glued to their TV screens, as the former NFL star turned actor led a police chase in a Ford Bronco across California. Simpson was was on the run after his ex-wife Nicole Brown Simpson and her friend Ronald Goldman were found murdered. Eventually, he was caught and faced trial. Stunning many, in October 1995, he was declared not guilty. However, in civil court in 1997, he was judged liable for the battery and death of Goldman, and battery against Brown, and ordered to pay the families $33.5 million. To date, he has reportedly paid only a small fraction of that. In the meantime, he’s served nine years in prison for armed robbery.

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

Jussie Smollett
After the “Empire” Actor Staged a Hate Crime Against Himself, He Was Sentenced to 150 Days in Jail

Reese Witherspoon
The Footage of Her Arrest for Disorderly Conduct in 2013 Went Viral

Conor McGregor
After Smashing a Fan’s Phone in 2019, the Former UFC Champ’s Arrest Video Spread Online

Steve-O
The “Jackass” Star Was Arrested While Live Streaming His Protest Against Seaworld on Social Media in 2015

Matthew McConaughey
In 1999, the Actor Was Found Nude, Intoxicated, & Playing Bongo Drums at Home in the Early Hours

#1: Bill Cosby

For decades, comedian and actor Bill Cosby had a reputation as America’s dad. That all fell apart in 2015. After comedian Hannibal Buress referred to accusations of sexual assault against Cosby in 2014, other accusations poured in. Approximately 60 women have accused Cosby of sexual misconduct, battery, and assault, often after he drugged them. He was arrested in 2015, and after a mistrial, he was retried in 2018 and sentenced to three to ten years in prison. However, in 2021, the Pennsylvania Supreme Court overturned Cosby’s conviction due to a 2005 agreement between Cosby and prosecutor Bruce Castor. The trial was thrown out, and Cosby was released from prison.