Not everyone can pull off a mugshot like David Bowie and somehow make it look like an album cover. For most people, a run-in with the law is not a great look. Even celebrities. One minute they’re posing under studio lights with a glam squad on standby, the next they’re standing under flickering fluorescent bulbs at a police station, looking like they just lost a fight with reality. Perfect hair turns into bedhead. Designer outfits suddenly look questionable. And those confident smiles? Replaced with dazed stares that say, “How did I get here?”
Here’s a list of the worst Hollywood actor mugshots of all time.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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?
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.
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