1. Paris Hilton
We'll start the list off with a celebrity that is pretty much expected to have an arrest record. The infamous Paris Hilton got sentenced to 45 days in jail for violating her probation. Hilton, who gained fame through worldwide partying, went to jail on June 5, 2007, and was not allowed to be released. Superior Court Judge Michael T. Sauer ruled after a hearing that the famous wild girl was in violation of the terms of her probation in an alcohol-related reckless driving case.
2. Robert Downey Jr.
3. Justin Bieber
Pop star Justin Bieber was charged with drunk driving, resisting arrest, and driving without a street racing without a valid license in 2014 in Miami Beach. “What the f*** did I do? Why did you stop me?” Bieber asked the police officer at 4 am after the arrest. The singer, who was 19 at the time, was released from a Miami jail a few hours later with a $2,500 bond.
4. Felicity Huffman
The star says she plans on doing more community service than is required of her. Her daughter ended up going to Carnegie Mellon University.
5. Shelley Malil
During his first parole hearing, the actor admitted that a combination of jealousy and alcohol-fueled his plans to "annihilate" the victim. The girlfriend survived the attack and Malil states he is dedicated to rehabilitation and does not want to create another victim again.
6. Mike "The Situation"
Jersey Shore Star, Mike Sorrentino, better known as “The Situation”, got himself into a bit of a situation. The reality star served eight months in prison and was released just last year, September 2019 with a remaining two years of supervised probation and 500 hours of community service in his sentence. This was due to tax evasion as he failed to pay his taxes.
Sorrentino’s lawyer tried to push for probation to no avail. Even if you’re a household name, you must pay taxes for your own house!
7. Charles S. Dutton
Charles made the most of his time in the pen as he credits picking up a book of plays by black playwrights prior to entering solitary confinement, which sparked his passion for the dramatic arts.
8. Mark Wahlberg
Mark Wahlberg, whom famous series entourage is based of off, didn’t fully depict his life in the HBO series as he forgot to mention his arrest at 16 years old. The Ted actor harmed two Vietnamese men in one day with a stick. One of the men became blind from the unprovoked assault. Wahlberg plead guilty and was sentenced to two years in prison but only ended up serving 45 days of that sentence.
9. Sanjay Dutt
Sanjay Dutt, an Indian actor, was arrested under the Arms Act in April 1993 for possession of illegal weapons during the1993 Bombay bombings. The Bombay bombings were a series of 13 terrorist bombings. He was released in 2016 after serving his sentence.
He is a devout Hindu and says that "I am not a politician but I belong to a political family." In 2018 a biopic based on his life called Sanju emerged as the highest grosser of Indian Cinema.
10. Sean Penn
Fast Times At Ridgeman High actor Sean Penn is known for assaulting people throughout his career. In 1987, the Actor was sentenced to 60 days for punching an extra on the set of his film 'Colors'. This was while he was on probation for two recent assaults.
Penn only served part of that time due to his then-wife, the infamous Madonna, for not pressing charges on a brutal domestic encounter.
11. Jamie Waylett
Not even wizards can escape prison! Crabbe from Harry Potter was removed from the exciting franchise’s final two films because of his 2009 arrest. British actor Jamie Waylett was not only sentenced to 120 hours of community service for growing cannabis in his family’s home but also spent two years behind bars for participating in the 2011 England Riots.
This actor, the pride of Slytherin's house, was also found in possession of a Molotov cocktail at the time of his apprehension. We're positive that rule-abiding citizen, Hermione Granger was not happy to hear the news.
12. Christian Slater
Christian Slater, who played a sociopathic high school student in the movie Heathers, had his moments of breaking sanity. In 1997, the actor assaulted his girlfriend and a police officer while intoxicated. He plead guilty and subsequently spent three months in prison and three months in rehabilitation.
Slater also had a run-in with the law in 1989 where he spent 10 days in jail for driving drunk.
13. Martha Stewart
Martha Stewart sure wasn’t baking blueberry muffins when she was incarcerated. The TV chef was sentenced to 5 months in a West Virginia prison due to insider trading in 2004. After the charges were made it was thought that the situation would end her media empire, but once she was released in 2005 she made a comeback campaign and continues to be successful, with her company returning to profitability just a mere year later in 2006. The famous businesswomen also paid a fine of $30,000.
Today Martha Stewart and Snoop Dog have a reality TV show together called “Martha & Snoop's Potluck Dinner Party” where they bond over their time in prison.
14. Lil' Kim
Rapper Lil’ Kim is not "spitting the truth" as she spent a year behind bars in 2005, after lying to a grand jury about her manager’s involvement in a shooting. The shooting took place four years before the trial directly outside of a radio station in Manhattan. Lil’ Kim committed perjury for her friend and manager Damion Butler.
Video evidence on the night of the shooting shows Damion opening the radio station door for the singer, who testified in court that she did not see him the day of the shooting.
15. Nicole Richie
It didn't take long for socialite Nicole Richie to follow her friend, Paris Hilton's path of partying her way to jail. In 2007, the celebrity pleaded guilty to driving under the influence of drugs. Richie was sentenced to four days in jail. The Simple Life stars were behind bars only a month after each other, proving just how interconnected their lives really were.
Richie was also fined $2,048, which is mere pennies for the rich star, and was placed on three years probation. She was also ordered to enroll in a rehabilitation program. Today Richie is a wife and mother and hopefully setting a better example for her own children.
16. Kiefer Sutherland
British actor, Kiefer Sutherland, wasn’t always on the good governmental behavior he was on in Designated Survivor when he served 48 days in jail in 2007 after a DUI. Sutherland also violated the terms of his probation and had to partake in an 18-month alcohol education program after the arrest. The actor also was required to attend weekly therapy sessions.
The therapy sessions seemed to work, as Sutherland is now an incredibly successful actor on an acclaimed Netflix series.
17. Lil' Wayne
Free Weezy became such a public plea that the own singer Lil Wayne named his album “Free Weezy Album” after being freed. The rapper spent eight months in prison in 2010 after being caught with drugs. He originally was sentenced to a year at Rikers for having illegal weapons and marijuana on his tour bus.
Due to good behavior, his sentence was reduced to 242 days. The rapper says a part of him still remains in the jail, where he entered a hell he’s never been able to escape. He says “I’ve unfortunately seen a lot of spirits get broken in this hell hole,” he wrote on his last day at Rikers. “I don’t wish jail on anybody.”
18. Ja Rule
Ja Rule, actor, and rapper spent over two years in prison for gun possession. The Fast And Furious actor was definitely furious when he had to stay in the slammer for an additional 28 months because he failed to pay his taxes after starting his original sentence in 2011.
He was released then brought back into custody hours later. Later that year he was released for good and has not been back to jail since.
19. Lindsay Lohan
Once she was the adorable twins in Parent Trip, but Lindsay Lohan grew up to have several run-ins with the law. The notable actress has been sentenced to jail several times and spent various times in jail for hit and runs, DUIs, and parole violations. Some of those include an hour in 2007, two weeks in 2010, and a full month in 2011. She spent another full month under house arrest later that year.
Now, the actress has a beach club on the party island of Mykonos in Greece where a video of her dancing went viral. Wouldn’t we all love to have a vacation house to run away to? Especially in these times!
20. Dustin Diamond
Dustin Diamond, Saved By The Bell star, spent four months in prison in January 2016. This was because two years prior the actor concealed a knife after disorderly conduct in a Wisconsin bar on Christmas Day 2014. In 2015 Diamond was convicted of felony charges and he began serving his sentence a year later.
In 2007 Diamond directed his own sex tape called Screeched- Saved by the Smell - a play on the words Samuel “Screech” Powers - his character in Saved by the Bell.
21. Blac Chyna
Blac Chyna was arrested for public intoxication and possession of controlled substances after boarding a flight to London from Austin in the United States. The model, who was in a relationship with Rob Kardashian, caused much stir as Blac has a son with Tyga, who was dating Rob’s half-sister Kylie Jenner.
Chyna isn’t the only one in the Kardashian squad who has been arrested and maybe she and Khloe laugh about their time in jail together at family dinners.
22. Danny Trejo
Danny Trejo's time in jail might have some responsibility for his troubled, weary face. The actor, known for his harsh demeanor, spent several years in and out of prison in the 1960s. Some of the charges included burglary, assault, and drug possession. The tough guy even did some prison time at the infamous San Quentin State Prison in California.
Nowadays, Trejo is donating food to 800 families of frontline workers, definitely making up for his time spent behind bars.
23. Khloe Kardashian
The famous Khloe Kardashian was arrested in 2007 for driving under the influence. In 2008 the millionaire went to jail to serve time for violating her probation. Kardashian faced a sentence of up to 30 days and enrolled in an alcoholism treatment program within three weeks of her release from jail.
Ironically, sister Kim Kardashian now spends her time freeing people from jail, such as Alice Johnson who was behind bars for almost 22 years for a small drug trafficking incident.
24. Tim Allen
Our favorite Santa Clause, Tim Allen, appeared on the naughty list in 1978 when the then 25-year-old served two years and four months in prison for drug trafficking. Allen was busted at an airport for cocaine possession. The actor avoided a life sentence by pleading guilty and providing police with names of other dealers - a different kind of Christmas list.
Allen was sent away (not to the north pole) for his attempt to traffic over 650 grams or 1.43 lbs of coke, a different type of snow.
25. Bill Cosby
The Cosby Show star, Bill Cosby had a major fall from fame recently, when it was exposed that he sexually assaulted women and children throughout his career. In 2010 several major media moguls cut ties with Cosby and stripped him of degrees and honorary titles. He was later found guilty on three counts of felony sexual assault, as expected. Cosby was sentenced to three - ten years in jail.
Cosby’s lawyers are filing for a motion asking the court to release the actor from prison and place him in house arrest due to coronavirus fears.
26. Lauryn Hill
We wonder if Lauryn Hill was thinking of her song “Nothing Really Matters” when she decided to evade her taxes. The singer and Sister Act 2 actor served three months in federal prison in 2013 for not paying her taxes.
The singer did not waste any time in prison and released her singer “Consumerism” the day after her release.
27. Teresa Giudice
Real Housewives of New Jersey Star Teresa Giudice became a prison wife in 2014 when she was sentenced to serve time after bankruptcy fraud. Teresa got 11 months behind bars but was allowed to serve her sentence separately from her husband Joe so she could remain with her four daughters.
Teresa was released two days before Christmas - a holiday miracle! We can only wonder if she had time to get her children's presents under the tree in those crucial 48 hours.
28. 50 Cent
Rapper 50 Cent spent 50% of a year (6 months) in a correctional boot camp for drug-related charges in 1994. The singer was only 16 years old when he was incarcerated.
29. Ryan Leaf
Ryan Leaf, former NFL Dallas Cowboys quarterback, was not winning at the game of life when he spent over 32 months in prison for breaking into homes. The quarterback committed a burglary in order to find painkillers for his drug addiction.
Leaf is now touching down to reality and using his story to help other former NFL players who are addicted to drugs and alcohol after retiring from the league.
30. OJ Simpson
The glove that didn’t fit saved this football player from a lifetime in Prison. O.J. Simpson did serve nine years for armed robbery and kidnapping. In 2017 Simpson was released early with the original sentence being 33 years.
The NFL Hall of Famer never served any time for his suspected murder of his wife Nicole Brown and her friend Ron Goldman but the case got brought even more to the publics' attention with the American Crime Series “The People Versus O.J. Simpson”. Rob Kardashian was O.J’s defense attorney which further propelled the family into fame.
31. Abby Lee Miller
Miller's new show was cut by Lifetime due to racists accusations. Miller said a black contestant was only on the show for a “sprinkle of color”. This dance mom seems to have a hard time staying out of the negative spotlight but as they say, no press is bad press.
32. Tom Sizemore
Saving Private Ryan star Tom Sizemore has spent nine months behind bars in 2007 for possession of “ice”, a controlled substance.
In 2003 the actor was removed from a film set in Utah after he sexually abused an 11-year-old. He has also been convicted of physically abusing and harassing his ex-girlfriend. The Black Hawk Down actor is hopefully on a path to becoming sober.
33. Michelle Rodriguez
The Fast and Furious star was driving dangerously in 2007 when Michelle Rodriguez was sentenced to six months in prison for violating probation terms after a DUI arrest. The actress was released after 18 days due to overcrowding.
It seems that “overcrowding” is a reason a lot of celebrities in jail get released early for.
34. TI
T.I. was living his life for 11 months in prison for violating the terms of his probation. The hip-hop star was arrested for possession of the drug Ecstasy in 2010.
The singer got in trouble during his time for getting pleasured by his wife Tiny during a jail visit, which is strictly prohibited. We're thinking Tiny couldn't hold herself back once she saw her man in that sexy orange jumpsuit!
35. Paul McCartney
“I still am hazy as to how that happened but it did,” Paul says when discussing the arrest “I had some marijuana in my suitcase and I ended up in jail [for] nine days. Scary!”
36. Chris Brown
37. Remy Ma
Rapper Remy Ma was convicted in 2008 of shooting a member of her entourage twice in the stomach. Ma spent six years in prison. She claims the member stole $3000 from her. The singer was also charged with assault, attempted coercion, and illegal weapon possession.
Once released in 2014, the Rapper made a comeback with the collaboration “All The Way Up’ with rapper Fat Joe. The song received two Grammy nominations. In reality, Remy really had nowhere to go but up!
38. Monica Bedi
Monica Bedi, the famous Bollywood actress, spent two years in a Portuguese jail in 2003 for possessing forged travel documents. Later on, she was convicted of the same charges in her native country.
Bedi was arrested with the convicted gangster and terrorist Abu Salem who she was in love with. The things you do for love...
39. Joe Giudice
With his wife Teresa, Joe Giudice was convicted for bankruptcy fraud in 2014. Joe got a 41-month sentence instead of the 11-month sentence Teresa was given. When Teresa served her time, Joe looked after his four daughters. Part of Joe’s sentence was him being deported back to Italy where he is from, as he is not a US citizen.
The entire family went to Italy to reunite and they appealed the deportation part of the sentence to get Joe back to the States. Joe's appeal got denied and now he is dating his lawyer in Italy, is divorced from Teresa, and hasn't seen his daughters in a year. Although Real Housewives of New Jersey had lots of drama, this case tops the cake and is full of way more craziness than the reality show.
40. Mike Tyson
We end the list with easily one of the scariest men on the planet - Mike Tyson. Known professionally as the “Baddest Man on the Planet”, Tyson is considered one of the best heavyweight boxers of all time. The professional boxer has been accused of hitting women multiple times, but what put him behind bars is being convicted of forcing himself on an 18-year-old in the 1990s. Tyson served three years in prison and to this day states that it was a false accusation.
The boxer made an appearance in The Hangover with a Tiger, where he was supposedly under the major influence of drugs and alcohol. Tyson got his infamous face tattoo in 2003 after his time in prison. We think if he had the tattoo in prison, inmates would have been even more scared of him than they already were, which trust us, was most definitely a lot.