Locked Up: 10 Celebrities Who Have Spent The Most Time In Prison

When we think of celebrities in jail, who do we think of? Lindsay LohanAmanda BynesParis Hilton and other celebrities being tried for DUIs (driving under the influence)? For most celebrities, such a charge is easy to brush under the rug. Take Paris Hilton for example, who was sentenced to 45 days in prison back in 2007 for violating her probation. After 23 days, the heiress was released on “good behaviour”.  Macaulay Culkin  had been detained for possession of marijuana and two controlled substances back in 2004, although he bailed himself out of jail after a couple of hours and for the fine of $540. He also received three suspended one-year prison terms, which was also enough for him to avoid being taken in by the police again. Amanda Bynes has been ticketed and detained in police custody for DUI-related offences and got out of most of the charges through financial settlements, probation and finally, psychiatric evaluation and commitment.

Those arrests were mainly for drug and alcohol-related offences. In the fantasy world of Hollywood, being apologetic and having enough money can be enough to insure that you can, at least, go home that night, in spite of the possibility of a trial. A trial for a famous celebrity like Hilton, Culkin or Bynes means probation, suspended sentences or psychiatric commitment, which is pretty minor in the grand scheme of things.

Although even famous Hollywood celebrities have skeletons in their closet that they can’t just walk away from after apologizing and paying a fine. These crimes have landed them in prison for sentences that span years, and even take away the possibility of bail or parole. Although what about the more serious crimes? Ones that involve drug trafficking or murder? What happens to celebrities then? Is money, fame and good behaviour enough to help reduce their sentences?

Our focus in this list is on the celebrities who have spent more than a month in prison, ranked from the least amount of time spent in jail to the most amount of time spent in jail.

10 Tim Allen: Served 2 years and 4 months in prison

Before his success as Tim Taylor on Home Improvement, Jason Nesmith in Galaxy Quest and Buzz Lightyear in the Toy Story trilogy, Tim Allen was a struggling comedian who resorted to less than reputable means to pay the bills. By that, we mean that he was arrested in Kalamazoo, Michigan for drug trafficking (possession of 1.4lb of cocaine) in 1978. He was sentenced for 3 to 7 years because he pled guilty and cooperated with the officials by giving up names of other dealers, but was paroled early after 2 years and 4 months in a Minnesotan correctional facility. Since then, he's only had a year's probation for a DUI in 1997. Otherwise, he's known to behave as a model citizen.

9 Don King: Served 3 1/2 years in prison 

In the 1970s Donald "Don" King was "the man" when it came to boxing promotion in the US. He promoted Muhammad AliMike TysonEvander Holyfield and several other big name boxers. Prior to his success, King had been involved in two murder cases. The first was in 1954, when he shot Hillary Brown, a man who had allegedly stolen from one of King's establishments. The courts determined the killing to be a justifiable homicide and no time was served. However, in 1966 he killed Sam Garrett, one of his employees, by stomping him to death over owing King $600. Originally on trial for second degree murder, his charges were reduced to manslaughter and he served 3 years and a half in prison. King’s crime was later pardoned in 1983 by Ohio Governor Jim Rhodes.

8 Maurice Clarett: Served 4 years in prison 

An excellent Running Back for Ohio State University, Maurice Clarett was a bit of a loose cannon off the field. While studying at OSU, he publicly criticized coaches, the university and its administrators for perceived offences against him, and was even in the middle of an academic scandal after a teaching assistant revealed to the New York Times that Clarett received special treatment from a professor. Later, Clarett was suspended for filing a false police report. He was drafted to the NFL in 2005, but was released from his contract with the NFL before even playing a single game. Then, in 2006, Clarett was arrested multiple times for robbery, fleeing the police after he made an illegal U-turn and resisting arrest after they caught up to him. He pled guilty and was sentenced to imprisonment for 7 ½ years, but was granted early release after almost 4 years, in 2010. Since then, he has joined mental health advocates to promote the expansion of Medicaid in Ohio.

7 Monica Bedi: Served 8 years in prison 

Monica Bedi is an Indian actress who has been working in Bollywood movies and television for 20 years alongside several popular actors and actresses in the industry. Unfortunately, she got herself involved with a fugitive, Abu Salem. In 2002, they were caught entering Portugal with forged documents. They served 4 years of jail time in Portugal before being deported to India in 2005. Bedi was convicted of passport forgery in 2006, but was released in 2010 because she had already served time in Portugal on top of her prison time in India, totaling 8 years of imprisonment. Since then, Bedi has continued her career as an actress, though she seems to stick to less mainstream films in India's film industry.

6 Charles S. Dutton: Served 10 years in prison 

Before becoming an actor of stage and screen, like Ma Rainey's Black BottomThe Practice and his starring role in the series Roc, Dutton was a high-school dropout who worked as an amateur boxer, nicknamed "Roc". In 1968, when he was 17, he was charged and convicted of manslaughter of a man who supposedly attacked him. He served 7 years in prison, before being released and then arrested again in the same year, 1975, for possession of a deadly weapon. He was sentenced for 3 more years. During this time, he read an anthology of black playwrights, which inspired him to get his GED and go to university. This led to his career as an actor and director for the next 27 years, which include roles on television shows like Law & Order: LA, Criminal Minds, American Horror Story: Murder House and The Good Wife.

5 Danny Trejo: Served 11 years in prison 

Maybe it was his early life of crime that helped him deliver such a believable character, but Danny Trejo is well known in Hollywood for his role as a "tough guy" or villain. Best known for his roles in Spy Kids, Once Upon A Time in Mexico and Machete, Trejo was initially a regular inmate of the California prison system for 11 years throughout the 1960's for crimes such as drug abuse and armed robbery, though there are conflicting accounts of exactly when he was an inmate. In prison, he became a champion boxer. Upon his release, Trejo, like Dutton, tried his hand at college, but left after one semester. Instead, Trejo achieved his career through meeting someone in the industry at a recovery meeting and training Eric Roberts for a boxing scene. The rest, as they say, is history.

4 O.J. Simpson: Sentenced to 33 years in prison with a chance of parole in 2017

Most are familiar with Orenthal James "O.J." Simpson's career as running back for the Buffalo Bills and San Francisco 49ers. Despite his many records and success, his career was cut short by the incredibly public trial, the People v. Simpson. Though he was acquitted in 1995, he was still found liable for the wrongful death and battery of Goldman and Brown in 1997 by a civil jury, and was ordered to pay $33,500,000 in damages to the Goldman family. In 2007, Simpson and a group of men were accused of stealing sports memorabilia at gunpoint. Although he admitted to taking the memorabilia, which he claimed belonged to him, he denied the used of any weapons. Within the next few days, he was arrested and charged with assault, use of a deadly weapon, kidnapping, robbery and criminal conspiracy. He was sentenced 33 years in prison with parole. Earlier in 2013, the case was reopened and Simpson was granted parole for certain robbery charges. He is currently in the Lovelock Correctional Center for 4 more years.

3 Phil Spector: 19 years to life in prison 

2 Shelley Malil: Life in prison, with possibility of parole in 2024

An Indian-born American actor of stage and screen, Shelley Malil is most well-known for his roles in The 40-Year-Old Virgin and Holes, though he has also achieved a Los Angeles Ovation Award as Best Featured Actor for his performance as Bottom in A Midsummer Night's Dream. While Malil seemed to have a promising acting career, that was cut short when he was arrested in 2008 for stabbing his ex-girlfriend 23 times. He was charged with attempted murder, because his ex-girlfriend lived, premeditation, causing great bodily injury, residential burglary and using a deadly weapon. In 2010, he was convicted and sentenced to life in prison, with possibility of parole in 14 years (now 10 years).

1 C-Murder: Mandatory life imprisonment

Corey Miller, ironically best known by his stage name, C-Murder, is an American rapper and actor from an equally musically inclined family - his brothers are Master P and Silkk the Shocker. Miller has 8 albums to his name, his first platinum album was released in 1998. In 2003, he was convicted of beating and fatally shooting a fan a year before, but a new trial was granted due to prosecutorial misconduct. Until then, Miller was under house arrest and a gag order regarding the court proceedings, though he was still allowed to make music and promote his novel. In 2009, Miller pled no guilty to two counts of attempted second degree murder, which involve a 2001 incident where Miller fired shots at the owner and bouncer of a night club who refused Miller entrance because of his weapon. Later that year, the murder retrial was held and Miller was convicted of second-degree murder and sentenced to mandatory life imprisonment.

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