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.
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.
