Top 10 Celebrities Who Have Been Imprisoned

Celebrities are people too, and often get in trouble with the law. With the recent release of rapper Lil Wayne from prison, it got us to thinking about other celebrities who have served prison time, for various offenses, over the years. This list features 10 previously (or, in one case, currently) jailed celebrities, but could easily be expanded to over 100 celebs who have been incarcerated at one time or another in their lives. With offenses ranging from drug possession to murder, these celebrities give jailbirds a bad reputation. Read on for 10 of the most infamous famous people ever to serve time behind bars.
1.      Lil Wayne

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Rapper Lil Wayne was sentenced to a year at Riker’s Island for carrying an illegal weapon. Some in the music industry say that he was only carrying the unlicensed firearm to get a bit of rapper street-cred. What really got him caught, though, was the act of smoking weed on the street. That caught the attention of the boys in blue, who subsequently arrested him when they found  the .40 caliber pistol on his body. So Dwayne Michael Carter, Jr. was charged not only with criminal possession of a weapon but also with marijuana possession. Lil Wayne was released from prison on November 4, 2010, with time off for good behavior.

2.      Tom Sizemore
Once a respected actor, Tom Sizemore is now better known for his brushes with the law. He was imprisoned in 2003 for assault and battery of his girlfriend, Heidi Fleiss, and served six months of jail time. After his release, he failed drug tests and violated probation and landed back in prison in 2007 for 16 months. Although at the time of this writing, Sizemore is out of prison, he is still under suspicious for stealing cell phones, so look for the actor to be serving more jail time before long.

3.      Mike Tyson

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Boxer Mike Tyson was infamously sentenced to prison for a rape conviction in 1991 when he was just 25 years old. Although he was sentenced to 10 years (6 in jail and 4 probation), Tyson served just over three years in prison with time off for good behavior. Tyson returned to boxing after his release from prison and became the heavyweight champion of the world once again, but it seemed that the big man had lost much of his original strength while behind bars.

4.      Lindsay Lohan

Remember the days when Lindsay Lohan was a talented actress? Me neither. OK, I’ll admit, she did perform well in family films like “Freaky Friday” and “The Parent Trap,”(hard to believe, but it’s true), but Lohan’s prison time for DUI and drug charges has unfortunately eclipsed her acting career. Lohan has bounced from prison to rehab and back for years, it seems, never learning her lesson. Maybe she needs some straight talk counseling from Robert Downey, Jr.? And if that does happen and it still doesn’t work, would there ever by a rehab center that can help her turn her life around?

5.      Snoop Dogg

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As a teenager, Snoop Dogg was arrested and imprisoned. However, he seems not to have learned anything from the experience. He has been in trouble with the law during the past two decades for numerous offenses including traffic violations, firearms possession, possession of drugs, even as an accomplice to murder. The rapper was even denied entrance to the United Kingdom because of his criminal history. Despite his rocky past, Cordozar Calvin Broadus (wouldn’t you go by Snoop Dogg, too, if that was your name?) continues to be arrested from time to time for drug violations and various and sundry other offenses.

6.      Tim Allen
You might not realize this, but actor and comedian Tim Allen served prison time before becoming famous. He was arrested in 1978 for drug trafficking when he was found with over a pound of cocaine in his possession. Because he gave up the names of other drug dealers, Allen’s prison sentence was lighter, at just three to seven years. In 1981, he was paroled for good behavior. Allen is one of the few celebrities to put his criminal past behind him and become a success.

7.      Phil Spector


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Music producer Phil Spector was found guilty of murdering actress Lana Clarkson in 2003. He wasn’t sentenced until 2009, when he received 19 years to life. While Spector always maintained that Clarkson had accidentally shot herself, other women came forward during the trial and accused him of pulling guns on them as well. Although it was a long time coming, justice was finally served in this case.

8.      Lil Kim

Rapper Lil’ Kim was convicted of conspiracy and perjury when she wouldn’t tell the truth about a friend’s involvement in a shooting in 2001. She served one year and one day in the Federal Detention Center in Philadelphia.

9.      Robert Downey, Jr.


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Another celebrity who finally seems to have turned his life around is Robert Downey, Jr. After years spent in and out of prison and rehab, Downey has been clean for some years now. The actor spent 18 months in jail between 1996 and 2001. He does not credit his jail time with teaching him anything, however. In an interview, Downey, who is now 46, said, “Jail didn’t help me any more or less than anything else. But I know I created that experience for a reason, and I’m only just starting to understand those reasons. I can’t believe I stayed out of the pen for as long as I did.” (

10.  Martha Stewart


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The famous queen of domesticity was arrested in March 2005 when she was found guilty of securities fraud and obstruction of justice. Martha Stewart was sentenced to five months in a federal correction center, five more months of electronic monitoring,  and two years of supervised release. Following her release from prison, Stewart returned to her media companies as if nothing had ever happened.

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