30 Celebrities You Forgot Were Arrested

Justin's 2014 arrest wasn't exactly a surprise — he'd been making headlines for questionable behavior for a while at that point — but the quality of his mugshot certainly was. That grin! If he was at all upset about being charged with DUI and resisting arrest, you'd never have known it from this photo. Justin settled the case later that year and in 2017 shared photos from the arrest with the caption "#neveragain."

Khloé was arrested back in March 2007 for DUI and later was sentenced to 30 days in jail for violating the terms of her probation; she ended up serving less than three hours of her sentence due to overcrowding. As of 2016, both Kim Kardashian and Kris Jenner had framed photos of Khloé's mugshot in their homes.

Long before he was known as the Lord, Scott was arrested for driving while intoxicated in 2001. Scott, who was 18 at the time, pled guilty to driving while under the influence of alcohol. In 2014, his de facto sister-in-law Khloé Kardashian shared his mugshot to Instagram as part of her happy birthday message to him.

Back in 2016, shortly after she started dating Rob Kardashian, Blac Chyna was arrested for public intoxication in Texas. She was also charged with felony drug possession after police found ecstasy in her bag, but the charge was eventually dropped.

If you were alive and following celebrity gossip in 2001, there's no way you could forget this one (and you might even still have a Free Winona t-shirt tucked away in your closet). Winona was arrested after shoplifting more than $5,000 worth of merchandise from a Beverly Hills outpost of Saks Fifth Avenue. After her trial (pictured on the left), she was sentenced to probation and community service and received a fine.

In a move straight out of the Nate Archibald playbook, Gossip Girl star Chace Crawford was arrested in 2010 for possession of marijuana. He struck a plea deal that would erase the charge from his record if he completed community service and didn't get caught doing anything illegal again. His mugshot remains one of the finest examples in the genre.

Before she was famous, Nicki Minaj was arrested in 2003 for criminal possession of a weapon. And in case you were wondering — yes, this did happen around the time Nicki was working at Red Lobster. Shellfish can make you do crazy things.

In yet another iconic tale of celebrity misbehavior, Matthew McConaughey was arrested in 1999 after his neighbors filed a noise complaint. Cops found him naked and playing the bongo drums and arrested him for marijuana possession and resisting arrest; the drug charges were eventually dropped. "What’s wrong with beating on your drums in your birthday suit?" Matthew said in 2016. "I have no regrets about the way I got there."

If you're on the TMZ tour and they pull up to a random, landmark-less street in Los Angeles and ask you what happened there, read them this caption. In 1995, beloved rom-com actor Hugh Grant was arrested after receiving oral sex, in his car, from a prostitute named Divine Brown. He was placed on probation and received a fine; Brown was sentenced to 180 days in jail.

Paris has been arrested more than once, but it's this ridiculously perfect mugshot that always comes to mind first. Paris was first arrested in 2006 for DUI; this 2007 shot is from a related incident where she was pulled over and found to be driving on a suspended license. A judge famously sentenced her to 45 days in jail for violating her probation, but she stayed there less than a week and did the remainder of her sentence at home.

Paris's Simple Life costar Nicole Richie also had some legal trouble in the mid-2000s; this mugshot is from her 2006 DUI arrest. Officers pulled her over in California after she was seen driving the wrong way on the highway. Like Paris, Nicole was sentenced to jail, this time for four days, but she stayed only 82 minutes due to overcrowding.

Back in 2007, shortly after The O.C. ended for good (and well after the show killed off Marissa Cooper), Mischa Barton was arrested for DUI in West Hollywood. She was later sentenced to three years of probation. "We thought, 'Work hard, play hard,'" she said in 2013, discussing that period of her life with People. "I've learned a lot. I'm stronger now."

Cuddly R&B teddy bear T-Pain was arrested in 2007 for driving with a suspended license. Police had put out a warrant for his arrest because someone had seen him driving when he wasn't supposed to be; he surrendered himself and was released on his own recognizance.

Teen Mom star Farrah Abraham was arrested for DUI back in 2013; she was pulled over in Nebraska after almost hitting a police car. Farrah was sentenced to probation and fined $500.

Teen Mom 2 star Jenelle Evans has been arrested multiple times; this photo is from a 2011 arrest where she was booked for violating her probation. More recently, her ex-boyfriend Kieffer Delp was arrested for operating a meth lab.

In 2012, the iconic Fiona Apple was arrested in Texas and of course turned in an iconic mugshot. Police arrested her in Sierra Blanca after finding hashish on her tour bus. Willie Nelson and Snoop Dogg have also been arrested in Sierra Blanca, which is 30 miles from the Mexican border and thus home to a U.S. Customs and Border Protection checkpoint.

Just before he blew up with his debut album Room for Squares, John Mayer was arrested in May 2001 for driving with a suspended license. In 2009, John offered to donate $25,000 to charity if TMZ could turn up the mugshot. TMZ found it, as did the Smoking Gun, so John donated $12,500 each to two different animal charities.

Uncle Jesse was arrested for DUI in June 2015 and pled guilty to a misdemeanor; he was sentenced to three years probation and counseling. Shortly after the arrest, he checked into rehab for substance abuse and stayed there for one month.