At this point, there's not a lot our favorite celebrities can do to surprise us anymore, but we're always a bit taken aback when someone famous ends up in handcuffs. Over the years, there have been more than a few celebrity arrests that have made headlines, and some of them have resulted in some truly unforgettable mugshots that have gone down in pop culture history.
Some of these mugshots are so famous because of the arrests themselves, while others are simply because of the celebs in them — or because by virtue of being famous, these people look that good in a situation where most would look pretty rough.
From Justin Bieber to Khloé Kardashian, here are all of the most infamous celebrity mugshots. Some of these arrests were totally forgotten until now (hi, Reese Witherspoon), while others still come up in conversation regularly. But all of them ended in jail snapshots that will be impossible to erase from celebrity history.
Josh Duggar
In April 2021, Josh Duggar of 19 Kids and Counting fame was arrested by federal agents on child pornography charges — and he posed for this infuriatingly smug mugshot. Though he was released on bail days later, Josh's trial is set for November 2021. If convicted, he could end up facing some pretty hefty fines and prison sentences.
Mama June
In 2019, June "Mama June" Shannon from Mama June: From Not to Hot and Here Comes Honey Boo Boo and boyfriend Geno Doak were arrested at an Alabama gas station after a call made to police over a domestic disturbance. At the time of their arrest, she wasn't just picked up on domestic violence charges, but drug charges as well.
Lindsay Lohan
Though she's now been arrested multiple times, Lindsay Lohan's most famous mugshot is probably her first. After she was arrested in May 2007 for DUI and drug charges, she showed up to serve time in November 2007, resulting in her spending less than 90 minutes behind bars due to overcrowding in the jail.
Justin Bieber
Considering the fact that Justin Bieber started out as America's darling when his angelic voice arrived on the scene as a young teen, it was pretty jarring to see him in an orange jumpsuit. In January 2014, Justin was arrested for drunk driving, resisting arrest, and driving without a valid license when he was caught drag racing in Miami at just 19 years old, kicking off a period of rebellion.
Paris Hilton
Few people look this good in a mugshot, but leave it to Paris Hilton to defy the odds. In 2007, the heiress was sentenced to 45 days in jail after she continued driving on a suspended license, despite the fact that she'd already received (and signed) a traffic violation that proved she was aware of the situation. She only ended up behind bars for four days, though, with the rest under house arrest.
Khloé Kardashian
Much of Khloé Kardashian's arrest saga was captured on Keeping Up With the Kardashians, so many fans probably remember this part of the family's history. In 2007, Khloé was arrested for driving under the influence, and though she was supposed to serve jail time, she ended up being released after just a few hours.
Robert Downey Jr.
Taking it all the way back to 1996 — and long before we knew him as Tony Stark — some fans might remember when Robert Downey Jr. was arrested for possession of drugs and an unloaded Magnum handgun when he was pulled over for speeding. In 1999, a judge sentenced him to three years in prison, though he was released early in 2000 with his previous time served helping him bust out.
Amanda Bynes
Though Amanda Bynes started out as a teen comedy queen on Nickelodeon and in movies like What a Girl Wants, she eventually ended up caught in a downward spiral that landed her in jail. In April 2012, Amanda was arrested for a DUI after hitting a stopped police car, and that would turn out to be only the beginning of her troubles.
Snooki
Jersey Shore star Nicole "Snooki" Polizzi has calmed down a lot since getting married and having children, but in the height of her MTV days, she was definitely a wild child. In July 2010, Snooki was arrested in Seaside Heights, New Jersey, for disorderly conduct out on the beach. Judging by her mugshot, she was less than thrilled by the situation.
Shailene Woodley
Shailene Woodley has always made it a priority to stand up for what she believes in, so is it any surprise that this mugshot was taken while she was in the process of doing just that? In 2016, Shailene was arrested for criminal trespassing and engaging in a riot while she was protesting the Dakota Access Pipeline, and she later wrote an essay about the experience for Time.
Jenelle Evans
Former Teen Mom 2 star Jenelle Evans has been arrested on multiple occasions, but who could forget that she was willing to risk jail time in order not to miss out on the upcoming Kesha concert? In 2011, Jenelle was taken into custody after being charged with possessing drug paraphernalia — and it all went downhill from there.
Reese Witherspoon
Considering her arrest was so out of character, it's easy to forget that Reese Witherspoon was ever behind bars at all! But in 2013, Reese's husband, Jim Toth, was pulled over for driving under the influence in Georgia, and Reese (who later admitted she'd had "one drink too many") tried to stop the police officer from arresting him — infamously demanding, "Don't you know who I am?" — and landed herself a disorderly conduct charge.
Aaron Carter
In 2008, singer Aaron Carter — the younger brother of Backstreet Boy Nick Carter — was arrested in Texas after he was pulled over for speeding and discovered to be in possession of marijuana. At the time, Aaron was 20 years old and driving alone.
Bruno Mars
Add this one to the list of impressively good looking mugshots! In 2010, Bruno Mars (real name: Peter Hernandez) was arrested in Las Vegas when he was found with cocaine in the bathroom of the Hard Rock Casino. Later, he told GQ that he had been "really drunk" when that mugshot was taken, so he couldn't remember why he was smiling.
Tiger Woods
When golfer Tiger Woods was arrested for driving under the influence in 2017, he was found to have a whole host of substances in his system, including painkillers, sleeping pills, anxiety medication, and THC. At the time, he said that he had been attempting to treat his back pain.
Nicole Richie
Going all the way back to July 2007, reality star Nicole Richie was arrested in California and ended up pleading guilty to driving under the influence. This meant that she was sentenced to four days in jail by a judge, though ultimately, Nicole ended up spending a total of 82 minutes behind bars.
