Try as one might, not everyone can nail a perfect mugshot as effortlessly as David Bowie. Being thrown in the slammer has a heavy toll on anyone, celebrities included. While we’re used to seeing sharply dressed and carefully styled stars on magazine covers, a police station’s harsh lighting tends to strip away all that polish. From messy hair and dazed expressions to fashion choices that also deserve prison sentences, here are ten of the most unfortunate celebrity mugshots ever snapped.
21. Prince
In 1980, opening for Rick James, Prince learned touring comes with odd risks. Keyboardist Dr. Fink spotted an emergency bullhorn on a plane and thought, perfect stage prop. As Fink recalled, “the pilot comes out and announces, ‘it has come to our attention someone has removed some emergency equipment from the airplane.’” Sky marshals searched. Prince, age 22, chose loyalty and joined Fink in jail. It became a fan meetup. He signed autographs from jail. Good thing he didn’t do serious prison time with that hairdo.
20. Megan Thee Stallion
After her 2015 mugshot popped back up, Meghan Thee Stallion went live on Instagram to shut it down. You’ve seen the clips. She said the jail stop came after a fight with an ex-boyfriend, not some wild myth. Yeah, before she was Meghan Thee Stallion, she was Meghan Thee Bail Queen.
19. Keanu Reeves
Keanu Reeves picked up a DUI in May 1993 after cops spotted his Porsche drifting through Los Angeles. He stayed calm, paid a fine, and finished alcohol classes. No career damage. Neo and John Wick feel untouchable. That mugshot though. Less action hero, more chilled stoner energy vibes.
18. Cher
In 1959, Los Angeles, California, 13-year-old Cherilyn Sarkisian, aka “Cher,” posed for an arrest mugshot after “borrowing” a friend’s car and driving without a license. Ever tempted to take a quick spin on city streets? Don’t.
17. Phil Spector
Phil Spector looked like he’d rather be anywhere else on July 24, 2013: slumped, stone-faced, red tie doing all the talking. After Lana Clarkson died at his Los Angeles-area home in 2003, a judge hit him with 19 years to life. At 69, parole meant 88.
16. 50 Cent
In August 1994, New York State Department of Correctional Services snapped Curtis Jackson at 19. Before “50 Cent” sold records, he pleaded guilty to felony drug sales, heroin and crack cocaine. You love a comeback, right?
15. Donald Trump
In August 2023, the president surrendered at an Atlanta jail, where his mugshot quickly became a media storm. Booked under inmate number P01135809, he faced charges tied to allegedly trying to overturn the 2020 election. Bail? A hefty $200,000—paid before he walked out the door.
14. Jaime Pressly
On January 6, 2011, actress Jaime Pressly’s night in Santa Monica ended with police charging her with two counts of drunken driving. The My Name Is Earl star, then 33, was booked after failing field sobriety tests, turning a routine traffic stop into unwanted tabloid headlines.
13. David Cassidy
David Cassidy, 63, found himself in trouble on August 21, 2013, after police in Schodack, New York, pulled him over for forgetting to switch off his high beams. The former teen idol failed sobriety tests and was charged with felony drunken driving just 15 miles south of Albany.
12. Flavor Flav
Flavor Flav, born William Drayton, hit headlines on October 17, 2012, for all the wrong reasons. Police charged the entertainer with Battery Domestic Violence and Assault with a Deadly Weapon after a heated fight with his fiancée, where he allegedly threatened her teenage son with a knife.
11. James Brown
James Brown, the 70-year-old “Godfather of Soul,” wasn’t just famous for dance moves—he kept South Carolina courts busy too. In 2004, he was arrested for allegedly attacking his 33-year-old wife, Tomi Rae Brown. He pled no contest and walked out with a fine just north of $1,000.
10. Tiger Woods
While most will remember Tiger Woods smiling happily in some of the world’s most gorgeous golf clubs, the Palm Beach County Sheriff’s Office will probably remember him for his notoriously terrible 2007 mugshot.
9. Robert Downey Jr.
Downey Jr. has more mugshots than Iron Man movies at this point, but his 2001 arrest, one of the last before he went sober, captured the MCU icon at rock bottom. The silver lining is that the mugshot marked the beginning of RDJ’s legendary comeback.
8. Paul Reubens
Back in the ’80s, if you told anyone that Pee-Wee Herman would be arrested for indecent exposure, no one would believe you. It would be even harder to believe if you showed them Paul Reubens’ mugshot with long hair and without his signature smile.
7. Orlando Brown
We all saw Orlando Brown mature throughout That’s So Raven, but no one expected Brown to look so changed in his infamous 2018 Las Vegas mugshot.
6. Michael Jackson
One of the most divisive court cases of all time, Jackson’s arrest in 2003 for allegedly molesting minors left us one of the most unintentionally unsettling portraits of the King of Pop.
5. Matthew McConaughey
In true Matthew McConaughey fashion, the actor was arrested in 1999 for noise complaints, leading the Austin police to find him inebriated in his house, playing the bongos naked at 2:30 a.m.
4. Marilyn Manson
Manson has fallen from grace considerably recently, but in 2001, he was still the prince of darkness. That’s why it was so jarring to see him looking “normal” without any makeup in his Oakland County mugshot.
3. Heather Locklear
A veritable TV icon with roles in shows like Melrose Place and Dynasty, Heather Locklear shook her fans when her 2018 mugshot hit the internet. She looks disheveled and unlike the golden girl fans knew, revealing a chapter of personal turmoil few expected.
2. Bill Cosby
One of the most infamous celebrity mugshots of all time, seeing America’s Dad fragile and borderline expressionless, and knowing the crimes behind his arrest, forever tarnished his pristine reputation, even after his conviction was ultimately overturned.
1. Nick Nolte
We all have a bad hair day from time to time. Nick Nolte, on the other hand, had a bad “everything” day in his 2002 mugshot. From the crazy hair to the loud Hawaiian shirt and the vacant expression that betrayed his DUI conviction, Nolte went on a long journey towards sobriety after his infamous mugshot.
