Many celebrities have had run-ins with the law for one reason or another but there are some celebs who have been arrested who may surprise you. You might assume that celebs like Sean Penn, Lindsay Lohan, and Lil Wayne have been put in handcuffs multiple times and you would be right in doing so. Penn has been arrested 6 times, Lohan 5 times, and Lil Wayne 4 times. Martin Sheen, however, holds the record for most arrests as far as celebs go after he admitted in 2009 that he has been arrested 66 times. Wow. And the apple doesn't fall far from the tree since his son, Charlie Sheen, has been arrested multiple times as well (not nearly as many as 66 times but, hey, he tried).
Though there have been high-profile arrests of super stars in the past, some of the best celebrity arrest stories are about the ones who were arrested before they were famous. Frank Sinatra was charged with an archaic crime that will shock you, a future billionaire was arrested for driving without a license, and a famous rapper was charged with a serious crime while she waited tables at Red Lobster. Then there are the celebs who were arrested while they were famous but their mugshots and charges will definitely surprise you. You'll never guess which famous actor was charged with possession of an illegal substance after being found naked playing the bongos. Brace yourselves because this list is full of surprises.
15 Bill Gates
Someone took a wrong turn in Albuquerque! The craziest thing about a young, smiling Bill Gates being arrested was that he was actually arrested two separate times only two years apart. He was once arrested in 1975 for driving without a license and speeding and once in 1977 for driving without a license (again) and not stopping at a stop sign. Honestly though, he should have been pulled over by the fashion police for wearing that collared floral shirt with a blue sweatshirt over it. But hey, the Microsoft bigwig isn't known for his sense of style anyway. He's probably smiling because he's thinking about all of the people he will piss off one day when he creates Windows 8 in the future. Or he just really loves driving without a license. Lucky for him, the arrest didn't hurt his career too much. Word is he turned out okay.
14 David Bowie
While Bill Gates was getting busted for driving with a license in the 70s, David Bowie was getting into some trouble of his own but on a little bit bigger scale. Bowie looks stylish as ever posing for his mugshots after he and his pal, James Osterberg, Jr., and a groupie named Chi Wah Soo were arrested for possession of an illegal substance in Rochester, New York. The groupie, Soo, later said in an interview that Bowie invited her and two other women to a nearby hotel after she had caught his eye during the show. Unfortunately for Bowie, those two other women were undercover cops. Oh, and you might know Osterberg better as Iggy Pop. On the day of his preliminary hearing on 4/20/1976, he faced up to 15 years imprisonment for being in possession of "a half a pound of [this substance]." Crazy, right? Lucky for him, the charges were dismissed but Bowie never performed in Rochester again.
13 Matthew McConaughey
Like Bowie and many others before him, Matthew McConaughey too was busted for possession of an illegal substance. Getting arrested for being in possession of this may have been somewhat of a rite of passage for celebs in the past but now that recreational use is legal in California, it's going to be just a little harder to get busted for it. However, McConaughey's brush with the law is somewhat legendary now since the story is so bizarre. The story goes that the police found the Interstellar star in his Texas home way back in 1999 while he was playing the bongos and dancing naked while another man clapped and danced along. Sounds like fun, right? The cops didn't think so. McConaughey eventually put on pants and the charges were eventually dropped, though he did spend about 9 hours in jail. McConaughey has since said that he doesn't regret the incident at all.
12 Robert Downey Jr.
It’s really not a surprise that Robert Downey Jr. has been arrested at least once and it’s not even a surprise that he’s been arrested two or three times but it’s pretty shocking that he has been arrested for a whopping 6 times. Unfortunately, the Iron Man actor has said that he has been addicted to drugs since he was a child after his father had given him drugs when he was 8 years old. In 1996, Downey was arrested for possession of two types of illegal substances, and an unloaded handgun. He was sentenced to three years of probation and spent six months in jail. This was a pretty light sentence considering the charges but that’s what happens when you’re a celebrity. Fortunately for Downey, he recovered from his drug addiction and had a big comeback with films like Kiss Kiss Bang Bang, Zodiac, and, of course, Iron Man.
11 Pee-Wee Herman/Paul Reubens
Speaking of Pee-Wee Herman, it turns out that he is not the lovable character that we grew up watching. In 1991, the actor (whose actual name is Paul Reubens) was arrested in Sarasota, Florida for indecent exposure in an adult theater. Gross. But the story doesn't end there. The arrest brought a lot of attention to Reubens it sent his career into a nose-dive. He had a comeback in the late 1990s with films like Mystery Men and Blow but then his career took a hit again when he was charged with possession of obscene material improperly depicting a child. The only reason why he is not in prison for the crime is that his lawyer determined that the material was mistakenly included with the evidence in Reubens' case so the charges were eventually dropped. Even if he is not guilty of that particular crime, it's pretty obvious that he's a gross dude.
10 Nicki Minaj
Before Nicki Minaj was the successful rapper that she is today, she worked as a waitress at Red Lobster in Queens and went by her birth name Onika Tanya Maraj. When she was only 20 years old, she was arrested for criminal possession of a weapon with intent to use way back in 2003. She has also, allegedly, been arrested for shoplifting. When the mugshot was leaked on the internet, whoever decided to share the information also shared her social security number. Apparently Minaj was forced to get a new social security number after her credit score dropped due to the release of her SSN. In another reveal, the leaked photos also made it pretty clear that she has gotten some work down on her face but hey, that was already pretty obvious. It’s Hollywood, everyone gets some work done.
9 George Carlin
George Carlin is known for his comedy but there’s nothing funny about getting arrested...well, in this case it’s kind of funny. Carlin was arrested in 1972 by Wisconsin police after performing his famous routine, ‘Seven Words You Can Never Say on Television’ at Summerfest in Milwaukee. Apparently the seven words you can’t say on TV can’t be said in Wisconsin either. He was actually charged with public indecency for violating obscenity laws. The case was eventually dismissed with it was ruled that his language may have been indecent but it was not obscene. However, what the cops didn’t realize was that, right before they picked him up, he had some white stuff in his pocket. Maybe second to his love of profanity was his love of drugs and it was what caused him to completely forget his experience as the first host of Saturday Night Live in 1975 because he was “loaded on [the substance] all week long.”
8 Frank Sinatra
Back in 1938, Frank Sinatra was arrested for a crime that would garner millions of adoring female fans in the future. What was the crime? Seduction. The story goes that Sinatra was arrested after seducing an unmarried woman to engage in some inappropriate activities with him which ruined her reputation. Yeah, the 1930s were weird. Turns out that the woman was actually married so Sinatra was no longer charged with Seduction. Instead, he was charged with Adultery. The charges were later dropped but Sinatra did not stop his seduction, only he did it with his music. Before The Beatles and One Direction, there was Frank Sinatra who caused groupies to scream and swoon at the sight of him. Also, he had affairs with many famous women such as Marilyn Monroe, Joan Crawford, Judy Garland, Elizabeth Taylor, Grace Kelly. In these relationships, he definitely engaged in some inappropriate activities but you know what they say about old habits.
7 Wood Harrelson
Woody Harrelson has had several run-ins with the law and the first was in 1982 when he was arrested for disorderly conduct after the police found him dancing in the middle of the street. He was arrested in 1996 in Kentucky when he planted four hemp seeds in a symbolical attempt to challenge the state law which did not discriminate between industrial hemp and the green stuff. His most bizarre arrest happened in 2002 when Harrelson broke an ashtray in a London taxi and the event somehow ended with a police chase and a night in jail for the actor. However, the incident inspired his 2017 film Lost in London which is the first ever live-streamed movie. Harrelson later said that there was nothing funny about the event at the time but he found comedy in it later on in life which led him to make the movie.
6 Natasha Lyonne
Before Natasha Lyonne played a criminal on Orange is the New Black, she actually was a criminal. Lyonne first got her start on Pee-Wee’s Playhouse in the 1980s and made it big when she played Jessica in American Pie. She also starred in Everyone Says I Love You, a vastly underrated Woody Allen musical. Unfortunately, Lyonne got involved with drugs and she was arrested in Miami in 2001 after hitting a road sign with her rented car and then tried to flee the scene. According to the Miami Beach Police Department, she refused to take a Breathalyzer test on the grounds that she was “a movie star.” She pled guilty to driving under the influence and ended up with six months of probation and 50 hours of community service. Fortunately, Lyonne has recovered from her drug addiction and now plays the lovable drug-addicted inmate, Nicky Nichols on Orange is the New Black.
5 Larry King
In 1971, Larry King, was arrested in Miami on charges of grand larceny after being accused of the crime by a former business partner, Lou Wolfson. The story goes that Wolfson gave King some money that he didn’t pay back because he used the money to pay his back taxes and gambling debts. The whole scandal is very confusing and the story usually involves a connection to the Kennedy assassination investigation but basically, the future Larry King Live host was in a lot of debt after trying to keep up appearances and support his extravagant lifestyle. At the time he was a WIOD disc jockey and commentator for the Miami Dolphins games. He was fired from these positions after the news of the scandal broke but he was never prosecuted. The high-profile arrest derailed his career for a few years but he landed on his feet eventually.
4 Jane Fonda
While Jane Fonda was on her way to speak at a college in Ohio back in 1970, her bag was confiscated because of three envelopes containing pills. She was arrested for drug smuggling but it turns out that the pills were just vitamins. Fonda has since said that she felt that this arrest was a smear campaign meant to damage her reputation and stop her political activism. However, the headlines only helped to promote activism and it brought out bigger turnouts than ever. Besides her acting career, Fonda has long been known for her political activism, support of the Civil Rights Movement, and opposition to the Vietnam War. Though she has long been seen as a feminist icon, she recently confessed that it took her many years to understand why feminism is so important and she established the Jane Fonda Center for Adolescent Reproductive Health in 2001.
3 Al Pacino
In 1961, a car was pulled over by the police after he had been circling the block several times in a Rhode Island neighborhood. The officers found three men in the car wearing black masks and gloves. That’s pretty incriminating stuff already but there was also a loaded pistol in the trunk. Busted. The three men were Vincent J. Calcagni, Bruce Cohen, and Alphonse Pacino. They were arrested and charged with carrying a concealed weapon. The only reason the charges were dropped was because the men told the police that they were actors and they were on their way to an acting gig that required them to bring the pistol as a prop. Sure. Surprisingly enough, they let them go and Al Pacino went on to play several iconic criminals in films such as The Godfather, Scarface, Dog Day Afternoon, and Carlito’s Way.
2 Andre the Giant
In 1989, Andre the Giant was arrested in Linn County, Iowa for allegedly getting into a fight with a local television camera man. The incident occurred after a the filming of a WWE house show. Apparently the camera man in question was instructed to not to get any footage of show but he decided to get on the wrestler’s bad side by filming segments of the match anyway. It’s safe to say that it’s not a good idea to piss off literally the biggest guy in the world and this guy learned the hard way. Andre confronted the camera man and ripped the cable right out of the camera before putting the man in a headlock. How the camera man survived this attack, we’ll never know. The Princess Bride actor faced charges but never got any jail time. Though he is a wrestling legend, Andre the Giant was known for being incredibly gentle and kind man who just happened to be 7 feet tall.
1 Elvis Presley
When Elvis pulled up to a gas station in his $10,000 car in in 1950s, he quickly drew a crowd. Girls began to swarm and swoon so he got out of his car and started signing autographs. Unfortunately for him, there were some people who were not as taken with the singer as the fangirls were. Since he was blocking traffic and it was impossible to get to the gas pumps, customers began to get mad at the singer. The owner of the gas station, Ed Hopper, asked him to move his car and he allegedly said that he would move the car but never did. The confrontation escalated and the Jailhouse Rock actor hit Hopper in the face, leaving a gash at the corner of his left eye. In the end, he wasn't charged with any crimes but it did have an impact on his public image. The story of the hunky singer getting into a fight at a gas station became national news.