15 Celebrities That Went To Jail

The life of a celebrity sounds like the dream right? You are getting paid millions of dollars to do something you love. You have access to almost anything you want. People love you. But sometimes the celebrity life isn’t that glamorous. Over the years there have been many famous faces who have found themselves on the wrong side of the law. Caught up in scandals and behaving erratically, there is more than a handful of celebrities that went to jail for their misdemeanors.

Now not all of these people committed serious crimes. For every Mike Tyson or Phil Spector, there is a Matthew McCaonahuey or Jim Morrison. Nonetheless, if you do the crime, you do the time. To highlight some of the celebrities who have ended up behind the slammer, here are 15 of the most famous. 

1. Robert Downey Jr

He might be a big time actor these days, but during the 90s Robert Downey Jr hit his lowest ebb. Not only was his film career at a standstill, but he found himself spiraling out of control. Things took a turn for the worse in 1996 when he was pulled over by the police while speeding on Sunset Boulevard. He was found to be in possession of cocaine, heroin, and a .357 Magnum pistol. Then he broke into his neighbor’s house after a wild night out and slept in one of the bedrooms. This resulted in Downey Jr being given a three-year probation sentence that involved him having to take compulsory drug tests. When he missed one he was sent to county jail for six months. 

Upon release, Downey Jr seemed to be slowly getting his act together until another missed drug test in 1999 saw him sentenced to three years in jail. He served almost a year before being released. This final stretch inside seemed to do the trick, with Downey Jr sorting his shit out and eventually going on to play Iron Man.

2. Martha Stewart

Martha Stewart built a lifestyle business empire around her cooking skills. She has written books, starred in several TV shows, and also spent time behind bars. On June 4, 2003, Stewart was indicted by the government on nine charges relating to insider trading about stock she sold before the price went down. 

Found guilty, Stewart served six months at the Federal Prison Camp in Alderson, West Virginia. Given the nickname M Diddy by the other inmates, Stewart was a model prisoner during her short stay. While many thought jail might put an end to her career, Stewart had other ideas. Upon her release, she was everywhere. She got her own TV show, The Martha Stewart Show, released a new book, and did the publicity rounds. She’s even collaborated with Snoop Dogg to get some street cred. 

3. Tim Allen

Before Tim ‘The Tool Man‘ Taylor, Tim Allen served two years and four months in prison on drug charges. On October 2, 1978, he was arrested at Kalamazoo/Battle Creek International Airport in possession of 1.43 ounces of cocaine. Facing life imprisonment, Allen ratted out his dealers. After his short stay behind bars, Allen realized crime wasn’t for him and took up comedy. Considering his successful career in film and television, he made the right choice. 

4. Mark Wahlberg

People are quick to forget Mark Wahlberg was charged with some pretty heinous crimes as a youngster. The star of Boogie Nights, The Fighter, and Ted was involved in several race-related crimes as a youth. At 15 he attacked a group of African American fourth-graders, throwing rocks at them and calling them racist names. While he somehow managed to stay on the streets, he wasn’t so lucky the next time. At 16 he beat up a couple of Vietnamese-Americans while shouting racist insults. He was charged with his crimes and sent to prison. Although his initial sentence was two years, Marky Marky only served 45 days. 

You would think Wahlberg would have learned his lesson, but four years later he broke his neighbor’s jaw in an unprovoked attack. The case was settled out of court. While remorseful for his actions, Wahlberg’s troubled past is rarely discussed, proving if you are white and rich, you can get away with anything. 

5. Mike Tyson

Arguably the greatest heavyweight boxer of all time, Mike Tyson is another celebrity with a troubled past. Along with admitting to assaulting his ex-wife and being arrested for drug possession and DUI, Tyson served time for the rape of an 18-year-old woman. Sentenced to six years, Tyson was out after three. 

While you think something like this would derail his career, it proved to be the opposite. Tyson got back in the ring for a number of big fights. He bit Evander Holyfield’s ear, went bankrupt, started a podcast, and is now the owner of several very successful marijuana companies, making more money now than he did boxing. 

6. Matthew McConaughey

Alright, alright, alright… Texan heartthrob Matthew McConaughey found himself in a jail cell after a night of naked bongos. High as and kite, police were called to his home at 2:30 am and found McConaughey sitting on his porch naked playing bongos along to some Cameroean music. He also had weed in his possession, which is what he got arrested for. Although he only spent one night in the drunk tank, this is a hilarious story that helped shape the legend of McConaughey.

7. Lindsay Lohan

Throughout the mid-00s Lindsay Lohan found herself in and out of trouble. Drink and drugs dominated her life as she chose to party over acting. The former child star was arrested numerous times for being under the influence while driving and being in possession of a variety of drugs. She’s been to jail three times but each stint has ended prematurely due to overcrowding. The first time she only spent 84 minutes behind bars, which seems like a waste of time.

While she struggled with addiction and has entered rehab numerous times over the years, Lohan is finally on the straight and narrow and doing her best to get her career back online. 

8. Wesley Snipes

At one point in the 90s, Wesley Snipes was everywhere. Newjack City, Passenger 57, White Man Can’t Jump, and Demolition Man are just some of the monster films he was in. Snipes was making big time money, but someone forget to tell him he needed to declare his earnings to the taxman. Snipes was found to have submitted false tax refund claims in 1996 and 1997. He also didn’t file a tax return from 1999 to 2004. 

While he tried to fight the chargers, it was a losing battle. Instead of paying the $5 million he owed, Snipes was sentenced to three years in prison, spending the final few months on house rest. The moral of the story: pay your taxes.

9. Tommy Lee

Back in the spotlight thanks to the Hulu series Pam & Tommy, Motley Crue drummer Tommy Lee’s past indiscretions are being talked about again. During his tumultuous relationship with Pamela Anderson, Lee attacked his former wife during an argument. He served six months in county jail for the incident. He and Anderson divorced soon after his release.  

10. O J  Simpson

No list of celebrities that went to jail is complete without including O J Simpson. The former running back was a star on and off the field, getting in punditry and acting after his football career ended. Much loved by the American public, this all changed in 1994 when he was accused of murdering his ex-wife, Nicole Brown Simpson, and her new partner Ron Goldman. 

Somehow Simpson was acquitted of the murders, but his public profile was in tatters. After a civil suit filed by the victim’s families found him guilty and liable for $33.5 million, he moved to Florida to avoid having to pay. But it gets worse.

In 2007 Simpson was arrested for attempted robbery and sentenced to 33 years in prison. He served a minimum sentence of nine years. He is now a free man living in Las Vegas. 

11. Felicity Huffman

Here’s another case of how being famous helps when it comes to committing a crime. Actress Felicity Huffman was arrested for her part in an admission scheme where millions of dollars in bribes were paid by parents to get their kids into the best schools. One of the people involved was Huffman. Pleading guilty to a litany of crimes, her sentence was laughable. She only spent two weeks behind bars. She also had to pay a $35,000 fine and complete 250 hours of community service.  

Lori Loughlin was another celebrity that was convicted, serving two months in prison for her part in the scheme. 

12. Danny Trejo

A hardman both on and off the screen, Danny Trejo has seen it all. During a ten-year period between 1959 and 1969, Trejo was in and out of prison for a variety of drug-related offenses. While in prison he became addicted to heroin and also took up boxing. His final stint in jail began in 1966 at the infamous San Quinten State Prison. During a riot in the prison in 1968, Trejo hit a guard over the head with a rock. Looking at a life sentence, Trejo found god while in solitary confinement and went about changing his life. He entered a 12-step program, got sober, and achieved his high school diploma. 

After getting out of prison he started a landscaping business before he stumbled into acting. He went from an extra and consultant on Runaway Train to securing his first billed role in Penitentiary III before eventually picking up steady work throughout the 80s. Now Trejo is a bonafide star. His performances in Heat, Con Air, From Dusk Till Dawn, Spy Kids, and the Machete films made him an icon. His scarred face is easily recognized and along with his film career, he owns a number of restaurants, has written a book, and appeared in many video games. 

13. James Brown

The Godfather of Soul had plenty of brushes with the law during his lifetime. You name the crime and Brown probably did it. Theft, attempted murder, assault, possession, domestic violence, and rape are all on James Brown’s rap sheet.

His most publicized arrest occurred after he was involved in a high-speed car chase with police on Interstate 20. He was eventually arrested and convicted for carrying an unlicensed pistol, assaulting a police officer, and various drug and driving-related offenses. Sentenced to six years behind bars, he only served two.

Somehow, despite the trouble that followed him, Brown still had many fans. He continued to release music and tour right up to his death on Christmas Day, 2006.

14. Lil Kim

One of rap’s great spitters spent one year behind bars after lying about a shooting her friend was involved in. In 2005 Kim was convicted on three counts of conspiracy and one count of perjury for lying to a Federal grand jury. She did one year at the Federal Detention Center in Philadelphia and 30 days of home detention.

15. Phil Spector

The creator of the Wall of Sound production method was a flawed genius. While his mastery of music was incredible, Phil Spector had a few issues in his personal life. The producer of the Beatles’ Let It Be and the Ramones’ End of the Century became a recluse in the 70s, spending less time producing and more time indulging in drugs. His behavior became more erratic and on February 3, 2003, Spector shot actress Lana Clarkson in the mouth at his mansion. 

Spector claimed it was an accidental suicide after Clarkson kissed the gun. The first trial ended in a mistrial in 2007, but the retrail in 2008 found Spector guilty of second-degree murder. Sentenced to 19 years to life, Spector would end up dying in prison at the age of 81 in January of 2021. 

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