Say Cheese! 20 Celebrity Mugshots That Show the Darker Side of Hollywood

Say Cheese! 40 Celebrity Mugshots That Show the Darker Side of Hollywood

Getting arrested is never a glamorous affair, even if you’re a celebrity. For many of us, we can just put our run-ins with the law behind us and move on. That time you got pulled over for speeding wasn’t really that big of a deal, right? When you’re famous, getting arrested, booked, and having your mugshot taken can have life-altering effects. For instance, when you think of Nick Nolte the first image that probably comes to your mind is that infamous mugshot.

When your business is your image, mugshots can be a really big deal. For some celebs, a mugshot is an opportunity. Many know that their fame means interest and that getting a unique or even funny mugshot is a way to get free publicity. Whether they’re smirking, smiling, crying, or striking pose, some celebrities really know how to get a novel mugshot. We at Mamas Uncut decided to sift through years of celebrity mugshots to bring you the best of the best. Some funny celebrity mugshots have a story behind them too and we’ll be sure to share those as well. Here are the top 40 celebrity mugshots.

40. Nick Nolte

Say Cheese! 20 Celebrity Mugshots That Show the Darker Side of Hollywood
Los Angeles Sheriff’s Department

As we said, this mugshot of Nick Nolte is pretty infamous. From the disheveled Hawaiin shirt to his gravity-defying hair, this mugshot has it all. Nolte was arrested for DUI and later blamed the incident on the drug GHB. He described it in detail in his memoir writing, “It went viral — my hair wild, my expression unsettling, looking like an asylum inmate out for a lark. In 1992, People magazine had named me the Sexiest Man Alive, and now, 10 years later, I looked to all the world like a madman.”

39. Bill Gates

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
Albuquerque Police Department

Billionaire and speed-demon, Bill Gates was arrested in December 1977 in Albuquerque, New Mexico. The exact circumstances of this arrest are not known, but it is said to be for a traffic violation. He had been arrested earlier in 1975 for speeding and driving without a valid driver’s license.

38. Justin Bieber

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
Miami-Dade Police Department

Musician Justin Bieber is known for hits like “Sorry” and “Baby,” but he’s also known as a bit of a wild child. Before settling down with now-wife Hailey Baldwin, Bieber lived his late teens and early twenties in a sometimes-reckless manner. In 2014, he was arrested in Miami and charged with misdemeanor careless driving and resisting arrest without violence after police encountered him driving under the influence of mary jane and prescription pills.

37. Jeremy Meeks, aka “The Hot Felon”

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
City of Stockton Police Department

Jeremy Meeks is the only person on this list who became famous because of his mugshot. Meeks, a former member of the Crips, was arrested in 2014 in Stockton, California during a gang sweep. His mugshot went viral while he was in prison, solely because, at least according to the internet, Meeks is hot. Like really, really hot. So hot he earned the nickname “The Hot Felon.” Since his release from prison, Meeks has landed work as a model. See what thirst can do? Most fortuitous mugshot of all time!

36. Amber Portwood

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
Indianapolis Metropolitan Police Department

Teen Mom star Amber Portwood was arrested on domestic battery charges in 2019. It’s been a wild ride for the young mom who has struggled with mental health issues. This culminated with Portwood threatening her boyfriend Andrew Glenwood with a machete.

35. Flava Flav

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
Clark County Sheriff’s Office

Hip hop artist and reality TV star Flava Flav was arrested near Las Vegas in 2015 for a myriad of reasons. Charges included: driving under the influence, possession of mary jane, having an open container of alcohol, speeding, having an invalid registration and driving with a suspended license.

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34. Michelle Rodriguez

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
Los Angeles Century Regional Detention Facility

In December 2007, actress Michelle Rodriguez, best known for her roles on Lost, the Fast and Furious movies, and Girlfight, was booked into a Los Angeles County jail. She had failed to complete community service and alcohol monitoring during probation stemming from an earlier drunk driving arrest. She served six months in jail.

33. Snooki

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
Seaside Heights Police Department

At the peak of her Jersey Shore fame in 2010, Nicole “Snooki” Polizzi was arrested in Seaside Heights, New Jersey and charged with disorderly conduct. According to reports at the time, Snooki got very, very, very drunk and rowdy on a Friday night and was seen looking disheveled, falling all over herself, and basically and looking and acting “too drunk.”

32. Luann de Lesseps

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
Palm Beach County Sheriff’s Office

Real Housewives of New York City star Luann de Lesseps was arrested on Christmas Eve 2017 for kicking a police officer, public intoxication, resisting arrest with violence and crimes against a person in Palm Beach, Florida. She allegedly yelled at people around her, “I’m going to kill you all,” before her arrest. The holidays are tough, okay?

31. Heather Locklear

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
Santa Barbara County Sheriff’s Department

Melrose Place star Heather Locklear was arrested in 2008 in Montecito, California after she was spotted driving erratically in a parking lot. Police ruled out alcohol as a factor, but they determined that the actress was under the influence of prescription pills at the time. It would not be the last time Locklear was arrested. She was arrested again in 2018 for battery against emergency personnel.

30. David Bowie

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
Rochester Police Department

The late, great David Bowie was arrested in 1976 on pot possession charges. The legendary rocker was arrested in the early hours of the morning on March 21, 1976, following a concert in Rochester, NY. Police apparently confiscated half a pound of pot from Bowie and others with him at the time, including fellow musician Iggy Pop. Bowie was released on bond and eventually pled not guilty before a grand jury decided not to pursue charges further.

29. Aaron Carter

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
Habersham County Sheriff’s Office

Child rapper Aaron Carter was arrested in Georgia in 2017 for suspicion of driving under the influence and possession of pot. Aaron Carter is Nick Carter’s little brother, but maybe Aaron is the most real “bad boy” of them all. That hair. Just, wow.

28. Paris Hilton

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
Las Vegas Police Department

Heiress Paris Hilton is certainly no stranger to arrests or mugshots. At least three of her mugshots are in wide circulation on the internet. This one, taken in 2010, followed the reality star’s arrest for coke possession in Las Vegas. Hey, at least, according to her expression, she found the whole thing at least a little amusing…

27. Frank Sinatra

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
Bergen County Sheriff’s Office

Frank Sinatra, one of the most beloved singers history has ever seen, was arrested at the young age of 23 in Bergen County, New Jersey. The young crooner was arrested on charges of seduction and adultery in 1938. Essentially what happened is that he was arrested for sleeping with a woman (the “seduction” charge — yes, that really used to be a thing!), and the charge was later revised to “adultery” when authorities learned the woman in question was married. Charges were eventually dismissed.

26. Shailene Woodley

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
Morton County Sheriff’s Department

Actress Shailene Woodley, star of Big Little Lies and the Divergent films, was arrested on October 10, 2016. At the time, she was protesting the Dakota Access Pipeline in North Dakota. She was charged with criminal trespassing and engaging in a riot. She eventually entered a plea and served no jail time.

25. Reese Witherspoon

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
City of Atlanta Department of Corrections 

America’s sweetheart, Reese Witherspoon, was arrested in Atlanta in 2013 for disorderly conduct after she refused to leave the car she was in. Her husband, Jim Toth, was busy getting a field sobriety test at the time and was booked for DUI. We wonder if she used some of her law skills from Legally Blonde to get out of this one. We should take this mugshot as a warning because if it can happen to Reese Witherspoon, it can happen to anyone!

24. Shia LaBeouf

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
Chicago Police Department

Child actor turned grownup actor Shia LaBeouf has had many run-ins with the law over the years. He was arrested in 2017 on charges of obstruction, disorderly conduct, and public drunkenness in Savannah, Georgia. He was arrested in 2014 for disrupting a play in New York. The above mugshot was taken after his arrest in 2007 for misdemeanor trespassing in Chicago. The story goes that he drunkenly kept visiting the same Walgreens store and refused to leave when asked.

23. Jane Fonda

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
AP Images

It wouldn’t be a list of celebrity mugshots without Jane Fonda! The iconic actress and activist is still to this very day making headlines for being arrested while protesting. Her most iconic mugshot, above, was taken in 1970. Fonda had been making very powerful enemies by loudly protesting the Vietnam War, and she was arrested in Cleveland for — wait for it! — having vitamins in her luggage.

22. John Mayer

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
City of Atlanta Department of Corrections 

Welcome to the real world! Singer, John Mayer looks about as clueless in his mugshot as you’d expect after being arrested for driving without a license in Atlanta. We guess he found out there’s such a thing as the real world. It wasn’t a lie he could rise above.

21. Nina Dobrev and the Cast of The Vampire Diaries

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
Monroe County Sheriff’s Department

In 2009, Nina Dobrev and her Vampire Diaries castmates were all arrested in Smarr, Georgia. In addition to Dobrev, Sara CanningCandice Accola, Kayla Ewell, photographer Tyler Shields, and actress Krystal Vayda (who was not on Vampire Diaries) were arrested on disorderly conduct charges. The group was allegedly distracting drivers by dangling off a bridge, flashing cars, and otherwise being “disorderly” in public during a photoshoot.

20. Eminem

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
Macomb County Sheriff’s Department

Rapper Eminem is no stranger to trouble, and at the height of his fame in 2000, he was arrested not once, but twice. The above mugshot was taken after Eminem, aka Marshall Mathers, was arrested following a bar fight in Warren, Michigan.

19. Jay Z

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
New York Police Department

Rapper, mogul husband of Beyoncé, and… criminal? Jay Z was arrested in 1999 just as he was becoming the most famous rapper on the planet. Jay reportedly stabbed record producer Lance “Un” Rivera at a club in New York City. Jay was charged with felony assault with a deadly weapon, but he eventually pled guilty to misdemeanor assault and served three years’ probation.

18. Khloé Kardashian

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
The Los Angeles County Sheriff’s Department

Reality TV star Khloé Kardashian turned herself over to the police in 2018 after violating her probation. This mugshot is one of our favorites because you can tell that Kardashian knew it was coming. She was prepared! Her makeup is flawless and we’d guess she got her hair done beforehand as well. She was released just three hours after due to overcrowding. We really can’t keep up with this Kardashian.

17. Cher

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
Los Angeles County Police Department

Fun fact: A 13- or 14-year-old Cher was arrested in 1959 in Los Angeles, California. The charge? The teenager apparently “borrowed” a friend’s car and was driving around the city in it without a license. Teenage shenanigans! Cher apparently has little recollection of the event, but her mom shared the story for a Lifetime special in 2013.

16. Hugh Grant

Say Cheese! 20 Celebrity Mugshots That Show the Darker Side of Hollywood
Los Angeles Police Department

British actor Hugh Grant was arrested in Los Angeles way back in 1995. He was arrested for solicitation and none of the 90’s romcom experience prepared him for time behind bars. Why does this mugshot always make us laugh? It looks like he’s about to run away, so there’s that.

15. Lindsay Lohan

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
Various Los Angeles Area Jails

You didn’t think you’d read a list of celebrity mugshots and not see Lindsay Lohan‘s face, right? The child actor has certainly had her fair share of run-ins with the police over the years. Her mugshots have become something of a meme, in fact. Lohan’s troubles really began in 2007, when she was arrested for driving under the influence (DUI) of alcohol and coke possession after she crashed her car in Los Angeles. Since then, Lohan has been repeatedly arrested on charges of DUI, drug possession, and not following through on the terms of her various probations.

14. Al Pacino

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
Providence County Sherrif’s Department

In 1961, legendary actor Al Pacino was arrested in Woonsocket, Rhode Island for carrying a concealed weapon. Pacino and two friends were allegedly driving around the same block repeatedly while wearing black masks before being pulled over by police, who found a loaded .38 caliber in the trunk. Pacino spent three days in jail, but charges were later dropped.

13. June Shannon

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
Henry County Sherriff’s Office

Mama June, aka June Shannon, has had a few run-ins with the law. This particular mugshot is from 2008 after June was arrested for theft of child support payments and contempt of court. The expression the Here Comes Honey Boo Boo star is making says it all.

12. Joshua Jackson

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
Wake County Sheriff’s Department

Joshua Jackson, who is best known for playing Pacey Witter on Dawson’s Creek, was arrested in 2002 in Raleigh, North Carolina. The charge? Jackson, apparently under the influence of alcohol, assaulted a security guard at a hockey game.

11. Macaulay Culkin

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
Oklahoma City Sheriff’s Office

Child actor Macaulay Culkin grew up fast! In 2004, Culkin was arrested for possession of mary jane and two controlled substances without a prescription. The Home Alone actor plead guilty and was given three one-year suspended prison terms and ordered to pay a $540 fine. Did he tell the judge to ‘Keep the change, ya filthy animal!”?

10. Keanu Reeves

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
Los Angeles County Sherrif’s Department

Actor Keanu Reeves was arrested in Los Angeles in 1993, shortly after his rise to fame, for drunk driving. Police apparently pulled him over after they spotted him driving erratically. He admitted to being under the influence in order to avoid charges. But hey, of all the people on this list, at least Reeves can say he looks the best in his mugshot.

9. Nicole Richie

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
Glendale Police Department

Fashion designer Nicole Richie looks like she’s trying not to laugh in this mugshot. She was arrested in 2006 after her car was spotted driving the wrong direction on the highway in Burbank, California. Richie admitted to using pot and Vicodin before getting behind the wheel. Not living The Simple Life after all.

8. Robert Downey, Jr.

Say Cheese! 30 Celebrity Mugshots That Show the Darker Side of Hollywood
California Department of Corrections

Actor Robert Downey, Jr. went through a well-documented battle with addiction, which led to him being arrested multiple times in the late 90s and early 2000s. The above mugshot was taken in 2001 after he was arrested in Culver City, California for allegedly being under the influence of a controlled substance.

7. Armie Hammer

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
Hudspeth County Sheriff

Before he was eating peaches with Timothée Chalamet or letting his children suck on his toes, Actor, Armie Hammer spent some time in jail in Texas. The actor, who was driving a u-haul truck, was pulled over by the Hudspeth County Sheriff and pot was discovered. He made bail, but prosecutors eventually dropped the charges.

6. Blac Chyna

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
Austin Police Department

Model and Rob Kardashian‘s ex, Blac Chyna, was arrested at the Austin-Bergstrom International Airport in Texas in 2016. After getting kicked off of her flight to London for disorderly conduct, she was taken into custody by police in Texas and later found with ecstasy. We hate flying too.

5. Nick Carter

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
Monroe County Sheriff’s Office

Another one of the Carter boys made the list! Backstreet Boy Nick Carter was arrested in Key West, Florida in 2016 after he got into a barfight at the Hog’s Breath Saloon. The Monroe County Sheriff’s Office showed him the meaning of being lonely, behind bars.

4. Vanilla Ice

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
Lantana Police Department

Kind-of-rapper Vanilla Ice was arrested in Florida in 2015 for allegedly burglarizing the house next door to his. He was filming a reality TV show, Vanilla Ice Project, about renovating the home. That’s insane. Want to know something even crazier? Vanilla Ice’s real name is Robert Van Winkle. We call him Rob’ Van Winkle for short.

3. Chace Crawford

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
Plano Police Department

Gossip Girl actor, Chace Crawford gave us something to gossip about after he was arrested in Plano, Texas in 2010. As part of a routine traffic stop, an officer allegedly found pot on the actor and arrested him for possession. He looks like someone who worked at that Abercrombie & Fitch you went to in middle school.

2. Marilyn Manson

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
Oakland County Sheriff’s Department

Shock rocker, Marilyn Manson was arrested after grinding on a security guard at a concert in Detroit in 2001. Without his makeup, he looks like a lost dog. Not that creepy at all.

1. Bruno Mars

Say Cheese! 20 Celebrity Mugshots You Need to See to Believe
Las Vegas Metropolitan Police Department

“Uptown Funk” singer Bruno Mars allegedly had the funk up his nose. Mars was arrested in 2010 and charged with possession of 2.6 grams of blow. Perhaps that explains why he’s so cheesy in this mugshot.

We hope you enjoyed these mugshots as much as we have. If you are ever having a bad day or feeling down or just need a little pick-me-up, return to this list, dear reader. Seeing rich, beautiful, famous people at their worst is a tonic like no other. A celebrity mugshot will never fail you.

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