18 Shocking Celebrity Arrests, From Khloe Kardashian to Emma Roberts

Some celebrities seem like magnets for trouble (sorry, Lindsay Lohan) but not every star seems quite as suited for a mugshot. Many people were surprised to hear that these celebrities got in trouble with the law, mainly because we don't exactly associate those stars with rebellion... or because their alleged crime was so wild it's hard to believe it actually happened. So which celebrity arrests surprised us the most? Click through to read about which stars still have the ability to shock us with their arrest record.

Reese Witherspoon

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America’s sweetheart surprised everyone in 2013 — and not because of a killer film performance.

Reese Witherspoon

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The Sweet Home Alabama actress was arrested for disorderly conduct after she confronted the police officer who was attempting to arrest her husband Jim Toth. She later made a public apology and stated that she had “nothing but respect” for the police officer who was “just doing his job.”

Amanda Bynes

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Fans were in the dark about the former child star’s struggles with mental illness until her first arrest.

Amanda Bynes

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The former All That star surprised everyone when she was busted for driving under the influence in 2012. Sadly, it wasn’t long before Bynes displayed increasingly erratic behavior, which led to rehab stays and more arrests.

Paul Reubens

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As if Pee Wee Herman wasn’t creepy enough, this happened.

Paul Reubens

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Reubens was arrested in 2002 for possession of child pornography. Ugh.

Emma Roberts

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The American Horror Story actress shocked everyone when she was arrested in 2013.

Emma Roberts

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According to reports, Roberts was arrested in Canada after an altercation with her boyfriend (now fiance) Evan Peters. According to TMZ, the actress was arrested after police checked in on the couple and saw that Peters had a bloody nose. Peters did not press charges against his girlfriend and Roberts was released hours later.

Winona Ryder

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The Heathers actress became the butt of many jokes after she was arrested for this surprising crime.

Winona Ryder

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The ’90s icon was arrested for shoplifting from Saks Fifth Avenue in 2001. She was a good sport about the incident and even joked about it in her Saturday Night Live monologue. But still — really girl? Shoplifting?

Martha Stewart

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No one saw the professional homemaker’s arrest coming.

Martha Stewart

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Stewart was sentenced to five months in a West Virginia prison after being convicted of insider trading in 2003.

Haley Joel Osment

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The Sixth Sense actor was barely an adult when he shocked the world and got arrested.

Haley Joel Osment

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The former child star was arrested in 2006 after crashing his station wagon while under the influence. To make everything just a little bit worse, Osment was also caught with marijuana in his vehicle.

Shia LaBeouf

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It wasn’t the Fury actor’s first arrest that was his most surprising.

Shia LaBeouf

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LaBeouf was arrested in 2014 for interrupting the Broadway play Cabaret by lighting up a cigarette and generally acting like a drunken jerk. Apparently he was so ridiculous that the audience of the show assumed the actor was just doing another one of his performance pieces.

Justin Bieber

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Hey, it was bound to happen. Sorry, Beliebers.

Justin Bieber

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The “Boyfriend” singer took a page from Grease when he was arrested for drag racing in Miami in early 2014. It wasn’t the only charge — the singer was also arrested for driving under the influence and resisting arrest.

Fred Willard

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The American Wedding actor was arrested at a movie theater. You know, a “movie theater.”

Fred Willard

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Willard was caught performing a “lewd act” at a porn theater in Los Angeles. That’s extremely upsetting, because everyone knows that porn is really about the story.

Hugh Grant

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Thank God Grant can explain this awkward arrest in an English accent.

Hugh Grant

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The Love, Actually actor was arrested in 1995 after Hollywood police caught him having sex with prostitute Divine Brown.

Khloe Kardashian

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The youngest Kardashian sister was arrested at the rise of her fame.

Khloe Kardashian

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Kardashian was arrested in 2007 for a DUI, a charge she later poked fun at on Twitter by sharing her and brother-in-law Scott Disick’s matching mugshots.

Matthew McConaughey

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No surprises here — the Dallas Buyers Club actor likes pot. How his arrest for possession went down is the ridiculous part.

Matthew McConaughey

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McConaughey was arrested in his Austin home when cops found marijuana on the property. They also found McConaughey playing the bongos, totally naked.

Tim Allen

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Oh, so you know Allen as the voice of Buzz Lightyear from Toy Story? Welcome to where I shatter your childhood.

Tim Allen

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According to reports, the family-friendly comedian used to be a coke dealer. He was arrested in 1978 for possession of the drug, but ultimately was able to avoid prison time by telling the cops about 21 other dealers he worked with. And that, my friends, is why we have The Santa Clause.

George Michael

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The “Faith” singer’s crime will make you cringe.

George Michael

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In 1998 Michael was arrested in a Beverly Hills park for performing a “lewd act” in public. (Use your imagination. Or, you know, don’t.)

Will Smith

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The Fresh Prince may seem relatively wholesome, but his arrest record says otherwise.

Will Smith

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According to Radar Online, a then 20-year-old Smith allegedly asked his bodyguard to attack a record promoter at a party in Philadelphia. Smith spent the night in jail but the charges were later dismissed.

Mitchel Musso

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No one expected Hannah Montana’s best friend Oliver to get in trouble with the law, but like many Disney Channel stars before him… he did.

Mitchel Musso

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Musso was arrested for drunk driving in Burbank, Calif. in 2011. Due to his squeaky-clean record (you know, until the whole “getting a DUI” thing) he was released without bail.

Chris Brown

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The singer horrified the world after reports came out about his crime against another celebrity.

Chris Brown

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Brown was arrested for assaulting then-girlfriend Rihanna in his car during a dispute. Brown has since violated his probation from his 2009 charge.