Robert Downey, Jr.
Way before his time as Iron Man, RDJ was an actor who just couldn’t seem to stop getting arrested. However, his ‘99 drug arrest gave us a pretty good mugshot. Crooked placard and a smug grin land him on the goofy end of the mugshot spectrum.
One of the most well-known mugshots of all time from the case of the century. Simpson was arrested in 1994 after an infamous car chase and the murder of his wife, Nicole Brown Simpson, and her friend, Ronald Goldman.
Okay, it’s not fair that he gets to have a perfect hair day even while he’s being arrested. That’s so unfair. Arrested in 2014 for DUI, resisting arrest, and driving with a suspended license.
Arrested for suspected marijuana possession, drug paraphernalia, and resisting arrest, McConaughey obviously didn’t feel too bad about the whole incident. At least, judging by that smug grin he’s wearing.
Charles Dion McDowell
What neck of the woods was this guy caught in? McDowell was arrested in Florida for possession of several drugs and fleeing the police. His mugshot was posted to Facebook by the sheriff’s office where it quickly became a popular meme. This guy was up to his neck in charges!
Kimora Lee Simmons
Just because you got arrested for marijuana possession, doesn’t mean you shouldn’t pose for your photo. Except, instead of posing for a fashion photographer, she’s posing for the cops.
Arrested in 2002 for driving under the influence, Nolte’s mugshot was one of the most infamous and could be found everywhere for many years to follow. The wild combo of gravity-defying hair, a loud Hawaiian shirt, and a crazy look in his eyes give him a spot on this list of iconic mugshots.
Returning from speaking out against the Vietnam War at a fundraiser, Fonda was arrested and wrongfully accused of drug smuggling. The charge may have amounted to nothing, but that didn’t stop her rebellious spirit, which resulted in this amazing mugshot.
The “King of Cool” himself was arrested in 1972 for drunk driving and speeding. But, he doesn’t seem too upset about it as he throws up a peace sign for the camera.
Gates’s photo looks more like a yearbook picture than a mugshot, but here he is. The Microsoft founder was arrested for a traffic violation in 1977 and has all the best elements of an iconic mugshot: shaggy hair, tinted glasses, weird stripes, and floral combo, and a grin that says ‘I won’t be here long.’
He may only have half a beard, but he had a full stash of marijuana with intent to sell. Unfortunately for him, he wound up spending the stoner holiday (4/20) in jail. Maybe it wasn’t half as bad as he thought?
He definitely doesn’t look happy about this 2013 public intoxication arrest. Guess he’s not a happy drunk.
Riley Dee Lewis
Accused of assault after chasing two joggers with a knife, Lewis’s mocking mugshot makes him seem about as crazy as you’d expect.
Oh, the irony. The luck of the Irish obviously wasn’t with this guy when he was arrested for driving recklessly and with expired plates.
Hey, bird for brains! You better hope he doesn’t talk. Buckner brought his macaw, called Bird, to court, expecting it not to take long. Then, he was ordered to be arrested for violating the terms of his release on misdemeanor thefts. So, while waiting for a friend to come and get Bird, Buckner took his mugshot (one with the macaw and one without).
He looks like one of those crystal skulls from that one Indiana Jones movie. Rodriguez was arrested and charged with first-degree arson and attempted murder, serious charges on their own. But most people were too enraptured by his mugshot. In case you’re wondering, Rodriguez, wound up losing part of his skull in a car accident.
Honestly, she just looks bored with this whole DUI arrest. What a Girl Wants is to go home, apparently.
It doesn’t take Einstein to figure out you probably shouldn’t act inappropriately at a bus terminal.
That shirt probably wasn’t the best idea for a weed trafficker to be wearing.
Tammy Lee Hinton
I thought your wedding day was supposed to be the best day of your life instead of the worst? Hinton was arrested for felony identity theft and taken into custody still in her wedding dress and veil.
LeBeouf has been arrested a few times over the past several years, but his 2014 arrest for disorderly conduct, harassment, and criminal trespassing gave us a great mugshot. LaBeouf looks like he’s having a pretty good time in this goofy, grinning mugshot.
Dubbed the “Hot Felon” by adoring internet fans, Jeremy Meeks was arrested in a gang sweep in 2014. After police posted his photo on their website, his mugshot went viral, racking up almost 100,000 likes. While serving his sentence, he was recruited by a modeling agency and is now a thriving fashion model.
The Vampire Diaries Cast
These look more like yearbook photos rather than mugshots. Nina Dobrev, Candice Accola, and Sara Canning, along with two other members of the cast were arrested in 2009 for dangling from a bridge and flashing drivers on a highway. The whole group was charged with disorderly conduct.
Another celebrity who loves to pose for the cameras, no matter who the camera belongs to. The middle Kardashian clan member was arrested for driving under the influence in 2007.
Honestly, it looks like we’d be seeing this picture on Instagram rather than as a mugshot. Arrested in 2010 for possession of cocaine outside of a Las Vegas nightclub, Hilton still managed to look good for her closeup even after a night of partying and being arrested.
Fidel Gonzalez Gutierrez
Ho, ho, ho? More like no, no, no. It looks like Santa Claus wound up on his own naughty list this year. Gutierrez was arrested for six outstanding warrants related to the sale of cocaine. It looks like this Santa look-a-like brought a little bit of North Pole snow with him.
Arrested for felony cocaine possession at a Las Vegas hotel in 2010, Mars still managed to give us a cheerful smile for a strangely happy-looking mugshot.
Getting arrested must’ve been a real pain in the neck for this kid. 18-year-old Musser was arrested for trespassing, though most people were too distracted by his hickey covered neck.
Mekhi Alante Lucky
Attractive features and some stunning heterochromatic eyes, Lucky makes the second felon who managed to land himself a modeling contract thanks to his mugshot. Arrested for speeding and driving a stolen vehicle, Lucky’s mugshot went viral and landed him his now-thriving modeling career once he got out of the slammer.
Even Hollywood darling Reese Witherspoon has a mugshot, and it stunned fans. Witherspoon and her husband, Jim Toth, were arrested in 2013 for driving while intoxicated and resisting arrest.