Yahoo Lifestyle 21 Celebs That Have Been Arrested, And Wow, I Forgot About So Many Of These
Content warning: this article contains mention of violence and sexual assault.
On a recent episode of the comedy podcast TigerBelly, comedian Luenell spoke about the time she robbed $50K from a bank she worked for and went to jail.
Since so many other celebrities have been arrested for both small and serious crimes, I thought it would be interesting to do a roundup of a few of them. So, here are some of the most fascinating celeb arrests:
The charge: Lewd conduct
The story: In 1995, the British heartthrob was arrested after being discovered by police in a car receiving oral sex from a sex worker. Both he and the sex worker pled no contest, were sentenced to probation and a fine, and were required to complete an AIDS education program.
The charges: Grand theft, burglary, vandalism
The story: In 2001, Winona Ryder was arrested for stealing roughly $5,000 worth of clothes from Saks Fifth Avenue in Beverly Hills. Despite the store's multiple requests to drop the charges, the district attorney's office refused to do so, and Ryder was eventually convicted of grand theft and shoplifting.
Ironically, the trial (and Ryder's great outfits for its duration) began a longstanding friendship between herself and Marc Jacobs, whose clothes she was convicted of stealing. She first appeared in his spring 2003 campaign, and they have remained friends and collaborators since.
In a November 2002, Washington Post article about the trial, writer Robin Givhan wrote of Winona that "She may be a shoplifter, but she has impeccable taste."
Pool / Getty Images, Bloomberg / Bloomberg via Getty Images
The charges: Securities fraud (insider trading), obstruction of justice, lying to investigators
The story: In 2003, the SEC alleged that Stewart had engaged in insider trading with her stockbroker, Peter Bacanovic. Authorities were never able to prove insider trading, and the securities fraud charges were dropped; but during the course of the investigation, Stewart had lied to federal authorities multiple times. She was eventually convicted of obstruction of justice, conspiracy, and making false statements, and spent five months in prison, five months on house arrest, and two years on probation.
Fun fact: in the second photo, wherein Stuart is seen boarding her private jet after leaving prison, she is wearing a shawl that was handmade for her by another inmate!
4.Robert Downey Jr.
The charges: Possession of various drugs, including cocaine, heroin, and marijuana
The story: RDJ was arrested and convicted several times throughout the 1990s and early 2000s on charges of drug possession. Multiple times, he failed to appear for mandated drug tests, and served several prison sentences.
Downey was exposed to drugs and included in his father's drug use at a young age. The first time they did cocaine together, Downey was 8. "When my dad and I would do drugs together,” he once said, "it was like him trying to express his love for me in the only way he knew how."
The charges: DUI, resisting arrest, driving with an expired license
The story: Bieber was arrested in 2014 in Miami after being pulled over and failing a sobriety test. According to NBC News, Bieber was aggravated at the time of the arrest. He allegedly told the officer that he was 19 years old and was "just out having a good time. What were you doing when you were 19?" When the officer replied that he hadn't been driving around in a Lamborghini as a teen, Bieber allegedly said, "Yeah, well, I bet you didn't have millions of dollars in your bank account either."
In a 2021 Instagram post, Bieber said that the arrest was "not my finest hour." He reflected on feeling "unhappy, confused, angry, [misled], misunderstood and angry at God," and urged followers to "let the forgiveness of Jesus take over and watch your life blossom into all that God has designed you to be."
Handout / Getty Images, Kypros
The charges: DUI, possession of marijuana and cocaine, obstructing an officer.
The story: Hilton was first arrested in 2006 for driving under the influence. Her license was suspended, but she continued to drive.
In 2010, Hilton pled guilty to the latter two charges following her arrest in Nevada after being found with marijuana and cocaine. She pled guilty and was sentenced to community service, probation, and a fine.
7.Justin Timberlake
The charge: Driving while intoxicated
The story: Timberlake was pulled over and arrested after running a stop sign and swerving. He failed multiple field sobriety tests, and told the police that he had "had one martini and followed my friends home."
The arrest (and this mugshot) went viral after Timberlake allegedly muttered, "This is going to ruin the tour." The arresting officer, a rookie who did not recognize the pop star, asked, "What tour?" Timberlake replied, "The world tour." The officer was apparently unsure what he was talking about.
8.Chace Crawford
The charges: Possession of marijuana
The story: 24-year-old Gossip Girl star Chace Crawford was arrested in Texas in 2010 after police found a joint in his car. He was later cleared of all charges after completing 80 hours of community service.
9.Frank Sinatra
The charge: Seduction (and later, Adultery)
The story: In 1938, Sinatra was arrested in New York and charged with Seduction, a crime that usually applied to a young man seducing an unmarried woman based on false promises (usually involving promises of marriage), thereby ruining her reputation.
However... the woman with whom he'd slept was already married! The state changed the charge to one of Adultery, as he had been "carrying on with a married woman." The charge was dropped after Sinatra paid a $500 bond.
If you think that law is archaic, think again; until November of 2024, adultery was still a crime in New York state. But as of December, cheating on your spouse is officially legal!
10.Tim Allen
The charges: Drug trafficking
The story: Allen was arrested in October of 1978 at a Michigan airport after being found in possession of over a pound of cocaine in his luggage. He pled guilty to drug trafficking charges and served over two years in prison.
Nearly 20 years later, in 1997, he was arrested a second time, this time for DUI. He was put on one year of probation, went to rehab, and has remained sober in the years since.
11.Bill Gates
The reason: Running a stop sign and driving without a license
The story: In 1977, an early-20s Bill Gates was arrested in Albuquerque, New Mexico following a traffic stop. In a 2007 interview with Time magazine, Gates said of the incident, "They pulled me over, and I didn't have my license, and they put me in with all the drunks all night long."
12.Tiger Woods
The charges: DUI
The story: In 2017, Woods was arrested and charged in Florida with driving under the influence of five drugs, including Xanax, Ambien, and marijuana. Charges were later dropped after he pled guilty to a lesser charge of reckless driving.
13.Mick Jagger and Keith Richards
Kypros / Getty Images, Powell / Getty Images
The charges: Drug possession
The story: In 1967, Rolling Stones singer Mick Jagger and guitarist Keith Richards were arrested at Richards' Sussex home for drug possession following a police raid. Jagger was sentenced to three months in jail, and Richards got a year, but there was much public criticism of the proceedings. At the time, Mick Jagger was prosecuting the tabloid News of the World for libel for their less-than-savory coverage of him and his girlfriend.
14.Johnny Depp
The reason: Depp has faced multiple arrests, including those for assault. This image is from his 1994 arrest for criminal mischief
The story: In 1994, an allegedly drunk Depp was infamously arrested for his destruction of a hotel room following a fight with then-girlfriend Kate Moss. He had allegedly accused Moss of cheating on him, and though the hotel later dropped criminal charges, the results of the ensuing fight ended up costing him $10,000 in damages. Depp maintained that the damages were caused by a loose armadillo, which was never found.
15.Shailene Woodley
The charges: Criminal trespassing and engaging in a riot
The story: Woodley was arrested in 2017 at a Standing Rock reservation protest of the Dakota Access Pipeline, the construction of which has been a widely-covered controversy for nearly a decade. She live streamed her arrest and later opened up about it in interviews.
"I was strip-searched," she revealed in an exclusive interview with Marie Claire UK. "Like get naked, turn over, spread your butt cheeks, bend over. They were looking for drugs in my ass." She said that for three months after the protest, she shut her phone off following symptoms of post-traumatic stress disorder.
16.Lindsay Lohan
The charges: DUI, possession, grand theft, violating terms of probation
The story: Between May 2007 and November 2012, Lohan was arrested several times for various charges, including DUI, possession of cocaine, theft of a $2,500 bracelet, and one alleged assault of a woman in a nightclub (though charges were dropped).
17.Bill Cosby
The charges: Aggravated indecent assault, assault, battery, among others
The story: Cosby has been accused of sexual assault by over 60 women, some of whom were underage at the time of the assault. Although the statute of limitations had passed for many of the rapes, Cosby was finally tried for an assault that happened in 2004, and after an initial mistrial, was sentenced to prison in Pennsylvania.
Although the Pennsylvania Supreme Court upheld this verdict when Cosby appealed, they later overruled the conviction, citing an agreement with prosecutor Bruce Castor. He had served almost three years.
As of 2023 and 2024, Cosby is facing two new lawsuits for multiple rapes of a then-19-year-old comedy writer and the drugging and sexual assault of a then-17-year-old.
18.Jane Fonda
Kypros / Getty Images
The charge: Drug smuggling (dropped)
The story: In 1970, following her speaking appearance at an anti-Vietnam war fundraiser in Canada, Fonda was arrested at a Cleveland airport on suspicion of drug smuggling. The alleged drugs turned out to be vitamins.
Writing on her personal blog in 2009, Fonda discussed the arrest. She said of the incident, "I told [the police] what [the pills] were but they said they were getting orders from the White House –that would be the Nixon White House. I think they hoped this 'scandal' would cause the college speeches to be canceled and ruin my respectability."
19.Woody Harrelson
The reason: Disorderly conduct, resisting arrest
The story: In Columbus, Ohio, in 1982, police arrested Harrelson for dancing in the middle of a busy street and attempting to flee when officers arrived at the scene.
20.Jay-Z
The charges: First-degree assault
The story: Jay Z was arrested in 1999 by New York City cops after allegedly stabbing a record executive at the Kit Kat Club in Manhattan. Although he initially pled not guilty, he eventually changed his plea and was sentenced to three years' probation.
The victim, Lance Rivera, has since spoken out to say that Jay Z is not the person who stabbed him that night.
21.Matthew McConaughey
The charges: Public disturbance, resisting transportation
The story: In 1999, following a noise complaint at around 2:30 in the morning, officers discovered McConaughey in his Austin home dancing naked and playing the bongos. Although police found a bong inside, he was unable to be charged with any drug-related offense because they hadn't entered with a warrant.
The resisting transportation charge came as a result of McConaughey "struggling" with police officers who were trying to get him into the car. At the time, reporter Bob Banta wrote that "People in the lobby of Municipal Court — most of them waiting to pay parking tickets — cheered McConaughey as he exited the elevator with his attorney, Joe Turner."
