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Top 10 Most Unexpected Celebrity Arrests

VO: Phoebe de Jeu WRITTEN BY: Spencer sher
There have been a lot of surprising celebrity criminals over the years. The college admission scandal involving Felicity Huffman and Lori Loughlin is just the most recent of many shocking celebrity arrests. For example, did you know Bruno Mars had a criminal record? Or that Will Smith was arrested for assault? Join WatchMojo as we count down the celebrity arrests we didn’t see coming. And let us know in the comments your thoughts on Felicity and Lori’s crimes. Do you think they should go to go to prison for what they did?
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Script written by Spencer sher

Top 10 Most Unexpected Celebrity Arrests


Didn’t see that coming. Welcome to WatchMojo, and today we’re counting down our picks for the Top 10 Most Unexpected Celebrity Arrests.

For this list, we’re look at celebs with clean-cut images that you wouldn't expect to see in handcuffs.

#10: Winona Ryder

Getting caught shoplifting is bad. Getting caught shoplifting on camera is really bad. And getting caught shoplifting on camera when you’re one of the most recognizable actors on the planet is really, really bad. Such was the case for Winona Ryder back in 2001, when she was caught red handed trying to steal thousands of dollars worth of clothes and jewelry from a Beverly Hills department store. The Golden Globe winner was arrested and convicted of grand theft, shoplifting, and vandalism, and sentenced to 480 of community service, three years probation, and ordered to attend drug counselling. Ryder later admitted that she was suffering from depression at the time and had been under the influence of painkillers. Still, the debacle shocked Hollywood.

#9: Haley Joel Osment

If you were a director in the 90s and early 2000s and you needed a super talented kid to appear in your movie, your first call was to Haley Joel Osment. From 1994 to 2003 Osment appeared in a slew of critically acclaimed films, often helmed by A-list directors such as Steven Spielberg and M. Night Shyamalan. His performances were regularly met with critical acclaim and he was on the fast track to superstardom. However, like many child stars, Osment did not escape his youth unscathed. When he was 18, Osment was arrested and charged with driving under the influence after he crashed his car into a mailbox. We still can’t believe that Forrest Gump Jr. has a mugshot…

#8: Bruno Mars

With his clean-cut look, it’d be easy to assume Bruno Mars has always lived on the straight and narrow. However, it may shock you to learn that in 2010 he was arrested in Las Vegas for possession of cocaine. Fresh off the success of his debut solo single “Just the Way You Are”, Mars was out partying with friends when he was caught in the bathroom of the Hard Rock casino with a little Columbian bambam. He was quick to tell the arresting officer he’d never done drugs before, but in a 2013 GQ interview he admitted it wasn’t true, stating, “I don't know where that came from. I was really intoxicated.” He pleaded guilty and received a $2000 fine and community service.

#7: Hugh Grant

We’re STILL trying to wrap our heads around this one. In 1995, the same year of his Golden Globe and BAFTA winning performance in “Four Weddings and a Funeral”, Hugh Grant was arrested in L.A. for receiving oral sex from a prostitute in a public place. Grant was in the middle of a promotional tour for his upcoming film “Nine Months” and continued to appear on talk shows despite the embarrassing arrest. Late Night host Jay Leno famously asked the actor what he was thinking, to which Grant replied, "I think you know in life what's a good thing to do and what's a bad thing, and I did a bad thing.” He was actually dating ELIZABETH HURLEY at the time. Let that sink in.

#6: Martha Stewart

When you’re the head of a multi-million-dollar lifestyle empire, the last thing anyone expects is for you to get sent to prison. Alas, that’s exactly what happened to TV personality Martha Stewart in 2004. While America was busy watching her make the perfect apple pie, Stewart was receiving behind-the-scenes advice from stock broker Peter Bacanovic. He had inside knowledge that ImClone Systems stock was about to drop and advised Stewart to sell hers; which she did. This is commonly known as insider trading and it’s illegal! Stewart was convicted and sentenced to five months in prison. However, anyone who didn’t live through it might well have no idea it happened, as Stewart has since regained her spot atop the lifestyle mountain.

#5: Matthew Broderick


In the 80s Matthew Broderick was one of the hottest movie stars around. And yet, unlike so many young stars, his image was squeaky clean, bolstered by boyish good looks. That all changed in 1987. Broderick was driving in Northern Ireland with his girlfriend, fellow actor Jennifer Grey, when he crossed into the wrong lane and hit an oncoming vehicle. The collision killed a woman and her mother. Broderick claimed he had no recollection of the accident, or even, in his own words, “getting up in the morning”. He was initially charged with death by dangerous driving, but this was later reduced to careless driving and he was fined just $175. The family of the deceased called it “a travesty of justice.”

#4: Will Smith

To many, Will Smith is the “Bel-Air” raised, planet-saving, alien butt kicker we all wish we could be. However, for a long time the actor harbored a secret that few were aware of. In 1989, just as he was beginning to make waves as a rapper, Smith was arrested for his involvement in an assault against record promoter William Hendricks. According to reports, Smith told his bodyguard to attack Hendricks, who suffered a fractured orbital bone and was almost blinded. Smith was ultimately arrested and charged with aggravated assault and criminal conspiracy, among other things; and spent the night in jail. However, the charges were later dismissed, and Smith has insisted he played no part.

#3: Lori Loughlin & Felicity Huffman

If you’re wondering why these two made the list, then it may be time to come out from under your rock. In March of 2019, it was reported that actors Lori Loughlin and Felicity Huffman, of “Full House” and “Desperate Housewives” fame respectively, had taken part in a nationwide college admissions conspiracy. They were arrested and taken into custody by the FBI on two counts of mail fraud each. Loughlin and Huffman, along with dozens of other wealthy parents, had allegedly participated in a scheme to help their children falsify athletic and/or academic records. In fact, Loughlin and her husband have been accused of paying $500,000 to get their daughters on the USC crew team, a sport neither had even trained in.

#2: Reese Witherspoon


Few actresses encapsulate the moniker “America’s Sweetheart” better than Reese Witherspoon. The multi-talented celeb won over Hollywood in her early 20s and has continued to impress fans with her mix of funny, intelligent, and adorable on-screen characters. Off-screen, she appeared to be the same affable person she presented in films and TV roles. However, in 2013, the world saw a different side of Witherspoon and it got her in trouble with the law. After her husband was pulled over on suspicion of DUI, she got out of the car and began berating the officers. It got so bad they arrested her for disorderly conduct. The entire incident was caught on camera and no doubt caused Witherspoon a considerable amount of embarrassment.

#1: Tim Allen

Say it isn’t so Buzz! Sorry to disappoint you folks, but even Tim “The Toolman” Taylor has gotten in trouble with Johnny Law. Way back in 1978, Allen was arrested at Kalamazoo/Battle Creek International Airport for attempting to traffick 650 grams of cocaine. Yes, you heard that correctly. He pleaded guilty to the charges and managed to reduce his sentence by giving up the dealers he was involved with. Allen served a little over two years in prison and was released in 1981. Despite going on to have an extremely successful acting career, Allen would slip up again in 1997. This time he was arrested for DUI and received a year probation. Not actually too bad for a former drug trafficker!
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