The Top 10 Celebrities Who Have Done Hard Time

Posted: April 24, 2012 in Top Ten Lists

The Top 10 Celebrities Who Have Done Hard Time – according to

Some celebrities whimper, moan, and cry if they have to spend 10 minutes in prison– we’re talking to you Lindsay Lohan! While many celebrities receive preferential treatment if they’re locked up (and miraculously have their sentences drastically shortened) not all celebs serving time in the big house are as lucky.

Photos: Smoking Gun & Getty Images

10. Lil Wayne – One Year

Photo: Ray Tamarra/Getty Images

For the longest time Lil Wayne talked the talk, but never walked the walk. Now that he’s serving time his thuggish street image finally has some street-cred. The rapper’s ticket to jail was the result of carrying an unlicensed firearm. The pint-sized rapper was arrested after performing in New York when police spotted him smoking marijuana on the street. They also discovered a .40 caliber pistol on his person. Lil Wayne, whose real name is Dwayne Michael Carter, Jr., was charged with criminal possession of a weapon and marijuana. He pleaded guilty and was sentenced to serve time in New York City’s infamous prison, Rikers Island. Prison time hasn’t stopped the rapper from reaching out to his fans. Wayne has kept a blog on his website Weezy Thanx You where he has outlined his prison routine and his return to writing lyrics. According to reports, Lil Wayne is expected to be released from prison in November after getting time off for good behavior.

9. Lil’ Kim – One Year

Source: Smoking Gun

Lil’ Kim ended up in the big house because she refused to snitch on her crew. The rapper was convicted of three counts of conspiracy and one count of perjury for lying to a jury about her friend’s involvement in a 2001 shooting. During the trial of her co-manager Damion “D-Roc” Butler, and bodyguard Suif “Gutta” Jackson, who were charged with murdering someone outside the Hot 97 radio station in New York, Lil’ Kim told the jury she was not aware the two were at the scene of the crime. Security footage later showed all three exiting the building. Bummer for Kim. Lil’ Kim was sentence to one year and one day and served the entire sentence at the Federal Detention Center in Philadelphia.

8. Tom Sizemore – 16 months

Photo: Stephen Shugerman/Getty Images

Tom Sizemore’s first dance with the prison system came after he assaulted his then girlfriend Heidi “Madam Hollywood” Fleiss. He was sentenced to six months in prison and even though he violated his probation, failed numerous court-ordered drug tests, and was caught trying to fake a drug test with a Whizzinator, he magically did not serve any more jail time. That didn’t last long. Sizemore was only able to sidestep the law for so long and was back in court in 2007 for again violating his probation, this time in connection with another drug charge. The court wasn’t so kind to Tommy this time and he was sentenced to 16 months. He was given credit for 213 days already served and served another six months at the Peasant Valley State Prison. It doesn’t seem like Sizemore has learned his lesson. The actor is currently under suspicion for stealing cell phones from Verizon.

7. Tim Allen – 28 Months

Source: Smoking Gun

Before the funnyman was a successful sitcom star, he was a struggling stand-up comedian who relied on dubious means to make a living. Allen’s world started tumbling down in 1978 when he was nabbed at Kalamazoo/Battle Creek International Airport in possession of 1.4 lbs of cocaine. That’s a lot of booger sugar for personal use. Allen received a felony drug charge and quickly rolled over, giving up the names of dealers in exchange for a lighter sentence. Allen could have faced life imprisonment, but his plea bargain only netted him 28 months at the Sandston Federal Correctional Institution in Minnesota. Allen subsequently turned his life around and became a very successful sitcom actor and Disney star. Yet, you wonder if the folks he snitched on have forgotten…

6. Mike Tyson – Three Years

Photo: Eugene Garcia/AFP/Getty Images

Mike Tyson’s turbulent path to boxing immortality took a court-mandated pit stop in the Indiana correctional system shortly after his 25th birthday for a rape conviction in the summer of 1991. According to the testimony of his victim – Miss Black Rhode Island – Tyson invited her to his hotel room at around 1:30 a.m. (possibly to discuss politics or watch Golden Girls reruns). After arriving, she claimed that he became overly aggressive and eventually forced himself on top of her. Tyson adamantly disputed the charges, but due to his violent reputation and prior indiscretions, was found guilty and sentenced to 10 years under state supervision (six behind bars and four on probation.) He would serve just over 36 months due to good behavior and once again return to the ring. He would eventually become the heavyweight champion of the world one more time; though most critics contend his skills had greatly diminished – as evidence by his meltdown against Evander Holyfield.

5. James Brown – Three Years

Source: Smoking Gun

The Godfather of Soul may have found his voice singing in church, but that didn’t mean he was a saint. The singer had a long history of run-ins with the law. At age 16 he was arrested for theft and spent three years in reform school. Brown found himself locked up again in 1988 after a bizarre crime spree that can only be described as his inner demons getting the better of him. On September 24 he stormed into an insurance seminar high on PCP and carrying a shotgun. This resulted in a half-hour police chase that saw Brown drive across state lines from Georgia to South Carolina and back again. To end the chase police had to shoot out three of Brown’s tires. The “hardest working man in show business” was charged with failing to stop for a police officer and aggravated assault. He was sentenced to six and a half years in prison and ended up serving three years. In 2003 he was pardoned by the South Carolina parole board for his crime.

4. Don King – Four Years

Source: Smoking Gun
Photo: Steve Granitz/WireImage/Getty Images

Though King has been accused of more crimes than the clients he allegedly (and routinely) steals from, the only legal miscue that earned him a stint in prison came in 1966. Following an earlier murder charge 12 years prior (which he beat by claiming self defense), King was found guilty of second degree murder for “stomping” an employee to death over a $600 dispute. The would-be promoting icon would only serve four years in prison, though, as his lawyer worked out a deal to have the murder charge altered to a non-negligent manslaughter conviction. His haircut, however, continues to go unpunished.

3. Danny Trejo – 11 Years

Photo: AFP/Getty Images

Some actors start out as child stars, Danny Trejo started out as a child drug dealer. The 66- year-old Hispanic tough man spent much of his youth in and out of jail. He was once a promising boxer with dreams of fighting professionally, but ended up spending much of the ’60s serving time in some of America’s most notorious prisons. He did stints in Tracy Prison (1963-65), San Quentin State Prison (1965-68), and Soledad Prison (1968-69) on armed robbery charges and drug offenses. In a sense prison was the making of Trejo. He became the California State prison lightweight and welterweight champion and entered a 12 Step program. In 1985 while attending a recovering program he met a man who invited him to a film set, where he was offered a role as an extra. From there a career was born and he just recently nailed down the lead role in Machete.

2. Phil Spector – 19 Years

Photo: Handout/Getty Images

Phil Spector’s penchant for guns and rough housing women finally caught up with him when he was found guilty of murdering bit-part actress Lana Clarkson. His path to conviction was long and his numerous murder trials where a media sensation and one of the biggest celebrity criminal cases in the last 10 years. Spector’s first television trial ended in a mistrial because of a hung jury. His second ended with Spector being sentenced to 19 years hard time. The legendary music producer is currently serving time in the notorious Corcoran State Prison, where fellow inmates include Charles Manson. Spector has already become a victim of prison brutality and was severely beaten early this year. The assault left him with a bruised nose, black eye, and some missing teeth. Obviously someone didn’t take kindly to his array of big wigs.

1. O.J. Simpson – 33 Years

Photo: Handout/Getty Images

Karma finally caught up with The Juice. While once known as “that guy who literally got away with murder” O.J. Simpson finally got his just desserts and ended up in lockup. While acquitted of the murder of his ex-wife Nicole Brown Simpson and Ronald Goldman in 1995, a cloud of suspicion formed over the NFL star that never dissipated. Simpson was later found responsible for the pair’s wrongful death in a 1997 civil suit. A 2006 book he wrote titled If I Did It didn’t help his reputation. With all that, none would have expected a botched armed robbery to be Simpson’s undoing, but it was and it was spectacular.

In 2007 O.J. led a team of petty armed criminals as they stormed a Las Vegas hotel room in search of sports memorabilia which Simpson claimed to be his. The owner of the memorabilia said likewise. O.J. was charged with multiple felonies, including criminal conspiracy, kidnapping, assault, robbery, and using a deadly weapon. Members of his so-called gang quickly turned on him and testified against him. Simpson ended up being found guilty of all 12 charges and sentenced to a whopping 33 years in prison. Ironically, O.J. received his sentence 13 years to the day he was acquitted of killing Nicole and Ronald (I think someone was trying to tell him something). O.J is currently serving his time in the Lovelock Correctional Center where he is known as inmate #1027820. He will be eligible for parole after serving about 9 years.

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