Whether they’re arrested for DUIs or something even worse, some celebrities still try to look glamorous in their mug shots, but few pull it off. Even the most photogenic stars can look disheveled after an arrest, and mug shots are rarely forgiving.

See a few of the best and worst celebrity mug shots and find out why these celebrities ended up behind bars, or were at least detained for a few hours before being sent on their way.

Best Celebrity Mug Shots

Justin Bieber

Cheerful on his first arrest, Justin Bieber was charged with a DUI, driving without a valid driver’s license and resisting arrest, but that didn’t stop him from giving his most charming smile to the camera. 

Justin Bieber Mug Shot

Bieber’s behavior contributed to a White House petition to get him deported, but the Canadian singer is still smiling since the response was simply “Sorry to disappoint, but we won’t be commenting on this one.”

Paris Hilton

Paris Hilton Mug Shot

After repeated arrests for a DUI, followed by parole violations, Paris Hilton ended up spending 23 days in jail. Despite prison overcrowding, the judge wasn’t convinced that anything else would work, despite the socialite having some of the best celebrity mug shots.

Khloe Kardashian

Khloe Kardashian Mug Shot

Following a DUI, Khloe Kardashian was booked for failing her parole conditions, including enrolling in an alcohol class and doing roadside clean-up. The reality TV star managed to look great in her mug shot and only ended up spending 3 hours in jail.

Robert Downey Jr.

Robert Downey Jr Mug Shots

Seemingly happy as a clam, Robert Downey Jr. had one of the best celebrity mug shows when he was arrested in 1998 for being under the influence of a controlled substance. He was quickly released, but his smile probably faded when he was fired from his role on the TV show “Ally McBeal”.

Amanda Bynes

Amanda Bynes Mug Shot

While the actress and singer has a couple of really unflattering mug shots, she did keep it together for the camera in April 2012, after being arrested for suspicion of driving under the influence. Maybe it helped that this was her first arrest, the beginning of her legal troubles.

Jane Fonda

Jane Fonda Mug Shot

Back when protesters for human rights were arrested for “disturbing the peace”, Jane Fonda resisted arrest and had one of the best celebrity mug shots, thanks to her “fight the power” hand sign. After being charged for possession of pills, she was quickly released because the pills in question were... vitamins.

Worst Celebrity Mug Shots

Lindsay Lohan

Lindsay Lohan Mug Shots

After enough mug shots to make a photo album, Lindsay Lohan seems to have finally put her troubles with the law behind her. While her former friend Paris managed to look pretty good in all her mug shots, the same thing can’t be said about Lindsay.

Reese Witherspoon and Jim Toth

Reese Witherspoon And Jim Toth Mug Shots

Charged with disorderly conduct after verbally attacking the cop who pulled her husband over for a DUI, Reese Witherspoon ended up having one of the worst celebrity mug shots. As soon as the alcohol wore off, the actress publicly apologized, but her mug shot still haunts her.

James Brown

James Brown Mug Shot

Domestic violence is no joke, but the Godfather of Soul looks hilarious in his mug shot from 2004. The disheveled singer got off the hook with a simple $1000 bond, despite having been arrested for assault four previous times.

Heather Locklear

Heather Locklear Mug Shot

Looking completely bewildered, Heather Locklear has one of the worst celebrity mug shots when she was arrested for a prescription drug related DUI. While no traces of illegal drugs and alcohol were found in her blood, she had been under the influence of depression and anxiety medication.

Nick Nolte

Nick Nolte Mug Shot

Another hilarious mug shot, Nick Nolte’s photograph following his 2002 arrest for a driving under the influence showed the actor looking less than his best. Nolte ended up in a 90-day substance abuse program and was under probation for the following three years.

Michael Jackson

Michael Jackson Mug Shot

Accusations against Michael Jackson for child molestation have been following the superstar for years, but his second arrest on these charges ended up creating one of the worst celebrity mug shots. Two years after the arrest, he was found not guilty and cleared of all charges.