20 Celebrities You Didn’t Know Have Done Real Time in Jail

Who would have thought?! There are loads of celebs that we did not even know had gotten into trouble with the law. Sure, we all know about the high-profile cases such as Lindsay Lohan, Martha Stewart,

Who would have thought?! There are loads of celebs that we did not even know had gotten into trouble with the law. Sure, we all know about the high-profile cases such as Lindsay Lohan, Martha Stewart, and Nicole Richie. Yet there are so many other rich and famous people who have had to take that shameful walk into the judge’s courtroom.

From rape and manslaughter to drug possession and driving under the influence, these stars have done some pretty disgraceful things. This just goes to show us that even if you are rich, powerful, and famous, you are not above the law. This list of 20 Celebrities You Didn’t Know Have Done Real Time in Jail may shock you.

There are stars on this list who have sky-high careers right now, as well as some who have seemed to have vanished into thin air. While some of these celebs have rebounded nicely, others have stayed under the radar for various reasons. These are celebs with different ages, charges, and histories. Sometimes all it takes is the stress from being famous, while other times these problems stem from long-embedded personal issues.

We hope that we don’t need to make another list like this one, but you really never know.

20 Robert Downey Jr.


He may be an awesome actor now, and he seems to have his life together, but back in the day, Robert Downey Jr. was something else. Back in 1999, he was sentenced to 3 years in prison. The reason? Drugs. In a case that included an exasperated judge and a down-and-out Robert, the celeb was cited for his drug abuse and consecutive violations on his probation charges, which included the misuse of substances and weapons. The actor had checked himself into a variety of treatment programs, all to no avail. The 1999 trial was quite emotional, but this story has a happy ending! After all, Robert is on the top of his game now!

19 Wesley Snipes


In another 3-year sentence, actor Wesley Snipes was charged for tax violations. He served his time from 2010 to 2013 and was held from McKean Federal Correctional Institution in Pennsylvania and was later released to a residential site in New York that was under high levels of supervision. What kind of celeb just fails to file tax returns? One who commits tax fraud, that’s who! Hopefully Wesley (and other celebrities) have learned from this experience. The IRS will find you and they will get you good! The positive news is that we haven’t heard about any misdemeanors from Wesley ever since this incident.

18 Don King


Who is Don King? He is a boxing promoter who was sentenced to serving time in prison for some very serious charges. Back in 1967, Don was charged with manslaughter in the beating of a man to the point of death. While Don was OK’d for a murder charge originating from 1954, the 1967 charge was a huge deal and the boxing celeb was paroled in 1971. Yet, post-prison life, Don had great financial successes, which helped him to flourish in the 1980s and 90s. He ended up promoting some legendary boxing matches and was able to really cash in. Yet people also have a bone to pick; Don was criticized for banking on boxers’ successes.

17 Tim Allen


Whaaat? Tim Allen captured our hearts and our funny bones by acting in television and movies series such as Home Improvement and The Santa Clause. He was also that ever-popular voice for Toy Story’s Buzz Lightyear. Yet did you know that way back in the 1970s, Tim was busted for distributing and carrying cocaine around Michigan? Whoops! In fact, the actor almost had to face life in prison, but was able to scuttle out of it by being a tattle-tale and ratting out multiple other drug dealers. It is definitely hard to believe, especially considering that Tim is such an accomplished actor.

16 Lil’ Kim

For female rapper Lil’ Kim, it was one year and one day of prison time she served. She was sentenced to do some time for three counts of perjury and one count of conspiracy. It all happened back in 2005, and owned up to her actions, which she called “wrong.” Lil’ Kim was also required to pay a fine of $50,000 (which would be no sweat for her) and she was also sentenced to 3 years probation once her jail time was served. That was actually not a bad take-away, considering that she was initially going to have to serve up to two decades behind bars. We haven’t heard much from Lil’ Kim lately, but that may very well be a good thing!

15 Paul McCartney


What? A Beatle in prison? Yes, but only for a short period of time. The famed singer spent just over a week in prison. Nine days to be exact (and we thought there were eight days in a week!) This incident was back in 1980 when the much younger singer was nabbed coming into the Narita International Airport in Tokyo, Japan for carrying around half a pound of marijuana. We all already knew that drugs were part of the reason the Beatles were able to make such awesome music. Now that it is nearly three decades later, Paul is more chill about the whole thing, but it was probably crazy-scary at the time!

14 Paris Hilton


Do we really care that Paris Hilton spent some time in jail? Not really. In fact, she should be behind bars for being so blatantly dumb. Yet the reason for her jail time back in 2007 was for violating a previous probation. She was nabbed for relishing in the party lifestyle, including abusing alcohol and driving under the influence. Paris released a public apology, not that the world cared. She was then sentenced to a 45-day prison term at a women’s facility. It was either that, or spent 3 months behind bars. Of course, she tried to get out of it, and she even arrived late to her own trial. Psh.

13 Lil’ Wayne


Lil’ Wayne is one scary-looking dude. With all of those tattoos and that creepy voice, he would actually blend in quite well behind bars, in our opinion. In 2009, the rapper pleaded guilty to a sentence claiming that he was in possession of weapons in New York. He was released on bail, but was set for a trial soon afterward. The sentence surrounded an incident when the rapper’s tour bus was searched by authorities on suspicion of drug possession. Lil’ Wayne had some marijuana and a .40 caliber semi-automatic gun, which was loaded. Oop! So much for the rapper’s lifestyle being all glamorous and tough.

12 Christian Slater

Drugs are quite common among celebrities, it seems. In 1997, actor Christian Slater was sentenced to a 3-month jail term for using cocaine and then assaulting his girlfriend while under the influence of the drug. The incident occurred late at night in glamorous Los Angeles, California. Police rushed to the scene after being alerted that there was a misbehaving Slater going around shouting and acting violently. The actor was fighting and trying to punch his girlfriend at the time. The actor was taken into police custody and confessed that he had been using not only cocaine, but alcohol and heroin as well.

11 T.I.


Sure, in the last few years, T.I. has seemed to be turning this around. He had a weird reality show about his not-so-real reality and he was doing music – we think. Yet in 2009, the rapper was sentenced to a year and one day in prison (is this the typical rapper’s jail time or something? Huh, Lil’ Kim?) T.I. was also fined $100,300 for weapons charges. He had reportedly bought silencers and machine guns, citing a need to protect himself as the reason for the weapons possession. The rapper had given his body guard $12,000 to purchase the firearms, even though a 1998 felony charge for drug possession prohibited him from owning guns.

10 James Brown


James Brown was sentenced to jail time? Yup. In 1988, the funky-to-the-max singer was sentenced to a 6-year jail term after being involved in a car chase with authorities. He was then acquitted of assault with intent to kill. Brown’s lawyer fought for the singer, stating that the authorities were taking the chase much too seriously, although it was true that Brown had refused to pull over and stop when police initially tried to stop him on the road. In the end, Brown was guilty of two counts of aggravated assault and eluding the police. Hey, 6 years is better than the initial sentence of 30 years.

9 Vince Neil


It was over three decades ago, but Motley Crue band member Vince Neil was charged in the death of Hanoi Rocks drummer Razzle. The incident occurred on December 8, 1984 when Vince was driving a car, got into a crash, and consequently, had Razzle (who was a passenger in the car) killed. Of course, alcohol was involved in the car accident, and as Vince was driving around in Hollywood, he lost control of his car and collided with another vehicle on the road. Everyone in the crash had injuries, but drummer Razzle was killed at just 24 years of age.

8 Michelle Rodríguez


Michelle Rodriguez certainly makes a pretty prison attendee. The actress was sentenced to 180 days in jail in Los Angeles, California for violating her probation, which stemmed from hit-and-run charges and driving under the influence. Michelle, who shot to fame in the hit television series, Lost, was sent to Century Regional Detention Facility, a stuffy prison that is bursting at the seams with inmates. In fact, Lindsay Lohan and Nicole Richie have spent time there, too! The prison sentences here are often comically short. Yet the judge said that Michelle would not be granted furlough, early release, or home confinement.

7 Danny Trejo


Danny Trejo is best known for being a rough-and-tough actor in movies such as Machete. Yet before he shot to fame for his acting and his muscular bod, he served time in multiple prisons in California. He was a prisoner to himself, really. He was addicted to drugs, and often resorted to illegal actions in order to scrounge up enough money to pay for the substances. Apparently while he was serving in jail, Danny made a reputation for himself as being a tough fighting machine, and even boxed against other inmates! His bad behavior in various prisons may be the reason why he was shuffled around so much to other facilities.

6 Ja Rule


No one really pays attention to Ja Rule anymore, but he was sentenced to serve some jail time for possessing a gun (illegally of course) and also for evading taxes. He served his time in Ray Brook Federal Prison in New York and was also sentenced to house arrest for a short time after his release from prison. The rapper spent 2 years in the federal prison for pleading guilty back in 2010 to charges of attempted criminal possession of a weapon. That incident was the result of a 2007 scuffle with police when they discovered the rapper was in possession of a semi-automatic handgun, which was loaded. The rapper also failed to pay the taxes on his earnings from 2004-2006 ($3 million!)

5 Kiefer Sutherland


Kiefer Sutherland was sentenced to a 48-day jail term back in 2007, at the age of 40. He was charged with drinking and driving and did his time in California. He was quite cooperative and sincere during the trial and was allowed to serve his jail sentence in a private jail cell, a tiny one at that. On top of that, he had to do his duties as an inmate, helping to serve the meals to other inmates and helping out with laundry. Sutherland appeared to be quite embarrassed and unhappy with the whole trial process, portraying himself to be sincerely apologetic.

4 Richard Hatch


The public knows Richard Hatch from the first season of the hit television show Survivor. He was the winner of the one million dollar prize, and while most people were not very thrilled at Richard being the final winner, things got a bit more interesting after the show was over. Richard was sentenced to jail time after he failed to pay the taxes on his $1 million prize. He had already spent 3 years in jail for a 2009 case of tax evasion, in which he did not refile is 2000 and 2001 taxes. Richard also had to serve 26 months under supervised release and had to pay 25% of his gross income to the IRS.

3 Lauryn Hill


Perhaps being a Grammy-winning singer takes its toll on you. Just ask Lauryn Hill, who was sentenced to jail time and house arrest, as well as one year of supervised probation for failing to pay her federal income tax. She was spending time at a lower-supervision all-women’s prison facility in Connecticut for three months before moving on to house confinement. She also had to pay the penalties and the tax amounts for the taxes she evaded. Her prison sentence did end a few days early, though. Lauryn was able to go almost directly back to her music career, and will hopefully avoid those tax mistakes from now on!

2 Mike Tyson


If you were not paying attention to Mike Tyson back in the 1990s, then you may not remember that he was sentenced to a 6-year prison term. He was charged with rape and was initially supposed to get a 10-year prison sentence, but the judge whittled it down to 6. The judge also said that with good behavior, Tyson could be released from jail after serving just 3 years. Sounds like a nice deal for someone who was accused of rape! Tyson was just 25 years old at the time of the conviction, and during the trial gave an apologetic (yet slightly self-righteous) rant.

1 Jamie Waylett


Jamie Waylett plated Vincent Crabbe in the Harry Potter movies, and maybe he got a little too into the method acting. He took part in some riots in London, England and was sentenced to two years in prison for his involvement. He was convicted of violent and disorderly conduct, and he also stole some alcohol during the incident. He was initially charged with the intent of destroying or damaging property, but the charges were dropped, even though a photo showed him clinging to a gas bomb. Waylett was clearly dismayed by the whole thing and was even spotted in public with a large hood draped over his head.


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20 Celebrities You Didn’t Know Have Done Real Time in Jail