Top 10 Celebrities That Went to Prison

Top 10 Celebrities That Went to Prison

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They went from the big time to the big house. Welcome to WatchMojo.com, and today we’re counting down our picks for the top 10 celebrities who went to prison. For this list, we’ll only be looking at those celebrities who did prison time while in the limelight and will be turning a blind eye to those who served their time pre-fame.

Oh how the mighty had fallen. A video game star and a heavyweight champion one minute, shmuck rotting in a jail cell the next – but not without good reason. Although the boxer insisted it was consensual, evidence and testimony said otherwise, and so Mike Tyson was sentenced to six years in prison for the 1991 rape of 18 year old beauty queen Desiree Washington. Ultimately, Tyson spent three years behind bars from March of 1992 to March of 1995, during which time he converted to Islam. Post release, Tyson has had minor incidents with the law but none as infamous as this.

Although arrested for assault in 2002 – charges of which were dropped – Michelle Rodriguez is better known in legal circles for her alcohol and car related crimes. These include a 2003 DUI and hit and run, a 48 hour jail stint in 2004 and a five day jail stay in 2006 for drunk driving. That incident led to a 60 day sentence as it violated her probation in LA; however Rodriguez walked the same day due to overcrowding. In 2007, the actress was given 180 days as a result of not finishing a community service term but in the end only served 18, again due to overcrowding.

While NFL star Michael Vick had some past run-ins, including a 2005 lawsuit for allegedly and knowingly giving a woman herpes, 2007 was his landmark year for bad behavior. Things went sour when his father spilled the beans on Vick’s love for dog fighting. Investigations soon revealed that not only was Vick running a dogfighting ring, but that also he took part in the killing of as many as eight dogs. Because the activities crossed state lines, the case was made Federal and the footballer was sentenced to 23 months at the United States Penitentiary in Leavenworth, Kansas.

Genius, innovator, auteur, murderer. With a history of violence and odd behavior – including allegedly holding the Ramones at gunpoint and keeping second wife Ronnie Spector a virtual hostage – it was almost inevitable that Phil Spector would slip up eventually – and he did. Motivated by drunkenness and rejection, Spector shot and killed Lana Clarkson in 2003. Following a mistrial in 2007, the producer was tried again in 2008 and was found guilty on April 13, 2009. Despite claiming it was, quote, an “accidental suicide,” Spector was sentenced to 19 years to life. Given his age, he will likely never be released.

He may have been the godfather of soul and the hardest working man in show business, but that didn’t mean James Brown was above the law. As the result of a high-speed chase near the South Carolina/Georgia border in 1988, Brown was charged with driving offenses, assaulting a police officer, possession of an unlicensed gun, and – likely the source of his troubles – tested positive for PCP. While Brown stated the police had assaulted him and even shot at his pickup truck, the charges stuck and papa gotta six year jail term, but took it to the bridge in just a little over two.

Following a tip from stockbroker Peter Bacanovic, Martha Stewart dumped nearly 4000 shares of ImClone Systems stock a day before it was due to tank. The move saved Stewart more than $45,000 in loses, but cost her so much more. Ultimately found guilty of conspiracy and lying to investigators, M-Diddy was fined $30,000, served a penalty of over $130,000 and spent five months in the clink. Additionally, Stewart was unable to head a company for at least five years. CBS meanwhile ceased broadcasting her show and, as a final indignity, aired a TV movie about her prison life. Ouch.

#4: DMX

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With a rap sheet lengthier than his rap discography, DMX has claimed he only went to jail to spread the word of Jesus; however his multiple accounts of reckless driving, drug charges, DUIs, weapons charges, parole violations, and at least one charge of impersonating a federal agent likely had something to do with it. DMX was arrested and jailed in 2010 for violating the terms of his probation by drinking at a concert and clocked up four separate driving offenses in 2013. While in 2015, for a change of pace, the rapper and father of 12 was given six months in the hoosegow for failing to pay $400k in child support.

#3: O. J. Simpson

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You could almost feel sorry for OJ. Almost. Maybe? Although acquitted in 1995 for the murder of ex-wife Nicole Brown and her friend Ronald Goldman, and found liable for the same deaths in 1997, The Juice was eventually put in the slammer for... stealing his own stuff. In 2007, Simpson led a group of thugs to a hotel in Las Vegas and seized sports memorabilia he claimed had been stolen from him. However, with the involvement of guns, kidnapping, assault, criminal conspiracy and the whole thing being – you know – a robbery, the onetime rental-car spokesman was handed a 33 year sentence in the Lovelock Correctional Center.

Known on the big screen for his tough guy persona, one would expect Wesley Snipes to be chucked in the pen for something equally badass. Not so. Charged in 2006 with conspiring to defraud the United States, Snipes was jailed for not properly filing his taxes – that is, he didn’t file at all for six years. The actor neglected to file based on the premise that income-taxation is illegal; however the court disagreed and found Snipes owed millions in back taxes. As a result, the star of “Blade” – and many direct-to-video movies – spent December 2010 to April 2013 in the McKean Federal Correctional Institution. Before we unveil our top pick here are a few honorable mentions: - George Michael - Ja Rule - T.I. - Christian Slater - Lil’ Kim

Arrested various times throughout the 1990s on drug charges, things came to a head for Robert Downey, Jr when he was jailed in 1997 and ‘99 for missing court mandated drug tests. Serving six months in ‘97 and facing additional time in 1999, Downey hired the same legal team as OJ Simpson did in 1995 – only this time they failed to get their client off. The actor was given three years in a prison rehab facility but was given the go ahead for early release one year later. Drug arrests and lost roles continued until Downey eventually replaced drugs with meditation, yoga, and kung fu around 2003 and maintained sobriety by being, well... Iron Man. Do you agree with our list? Who’s your favorite celebrity jail bird? For more Shawshanking Top 10s published daily, be sure to subscribe to WatchMojo.com.