Robert Downey, Jr.: ‘Iron Man’ definitely did not save Robert Downey Junior from being imprisoned between 1999 and 2000. The actor committed a few parole violations related to multiple drug charges. He was then confined in a California substance abuse treatment facility and a state prison for almost one year.
Mark Wahlberg: “The Departed” actor assaulted two Vietnamese men during two separate occasions when he was 16 years old. He assaulted the first man using a stick, and knocked him unconscious. Wahlberg pleaded guilty for the two assaults, and was sentenced to two years for attempted murder. However he only spent 45 days in prison…
Sean Penn: The ex-husband of Madonna is known for his violent outbursts. The actor however was only imprisoned for one incident. Penn punched an extra on the set of “Colors”, which caused him to be imprisoned for 60 days while on probation for two prior assaults.
Christian Slater: Christian Slater pleaded guilty for assaulting his girlfriend and a police officer when he was under the influence of alcohol in 1997. He was sentence for three months in prison, and another three months in rehab. He was again imprisoned in 1989 for a drunk-driving charge.
Lil’ Kim: the Juwanna Mann actress was convicted for conspiracy and perjury, which lead her to be jailed for almost a year. Lil’ Kim lied in her testimony to a grand jury about her friend and manager, Damion Butler. The charges related to a shootout in front of a radio station. The actress testified that she had not seen Butler on that day, but video evidence was presented show Butler opening the door for Kim.
Kiefer Sutherland: Sutherland spent 48 days in jail in 2007 for violating the conditions of his probation. After his release, he went for an 18-month alcohol education program, together with weekly therapy sessions he had to attend.
Ja Rule: the “Cookout” actor was found guilty for illegal gun possession and was sentenced to two years of imprisonment in 2011. He, however, had to stay in prison for another 28 months for tax evasion.
Dustin Diamond: Dustin Diamond served four months in prison for disorderly conduct and carrying a concealed weapon (knife). The incident happened on Christmas Day 2014 in a Wisconsin bar. He was cleared of felony charges after one year.
Danny Trejo: Danny Trejo had a love and hate relationship with prison for several years. He was in and out of jail for burglary, drug possession, assault, and other charges.
Tim Allen: Allen was found to be involved in cocaine trafficking in 1978. His lifetime sentence was reduced to two years and four months by giving information about the other dealers. He was paroled in 1981.
Lauryn Hill: the singer and actress Lauryn Hill was found guilty for tax evasion in 2013. She served in a federal prison for three months. Despite her detention, she was able to release her new single entitle “Consumerism” on the same day of her release.
50 Cent: the rapper-turned-actor was guilty of multiple drug charges when he was 16 years old. He went in a correctional boot camp for 6 months.
O.J. Simpson: O.J. Simpson has been convicted over several high profile cases. He is still serving his 33-year prison sentence for kidnapping and armed robbery. Simpson is unqualified for parole until 2017.
Tom Sizemore: the actor has been found guilty of possession of methamphetamine. He served for nine months in jail in 2007. He was arrested while being on parole because of prior drug charges.
T.I.: he spent over 6 months in jail for federal weapons charges. The actor, however, spent another three months at a halfway house in Atlanta.
Chris Brown: the singer was convicted for a violent assault on his ex-girlfriend Rihanna. But during the period of his probation, he served few months in prison for another assault. He is now released but still under probation.
Monica Bedi: the Indian actress served in a Portuguese prison for two year due to possession of forged travel documents in 2003. She was again found be guilty of the same charges in India.
Mike Tyson: the undisputed heavyweight professional boxer was guilty of rape of an 18-year-old girl in the 1990s. He served three years in prison even he contended that the accusations are wrong.
Shelley Mailil: the actor was sentenced to life in prison for murdering his girlfriend in 2010. The “40 Year-Old Virgin” actor is now incarcerated at Ironwood State Prison in California.
Charles S. Dutton: 17-year-old Dutton was found guilty of manslaughter after involving in a fight that resulted to the death of a man. He served seven years in jail. An additional three years of imprisonment was imposed on him for weapon charges.
Sanjay Dutt: the Indian actor served 7 months in prison from 2006 to 2007 due to weapon charges. He is currently serving his sentence for additional weapon charges related with the 1993 bombings in Mumbai.
Lillo Brancato, Jr.: the actor served 8 years in jail for two crimes, burglary and second-degree murder. Together with another person, they robbed and killed an off-duty police officer. In 2013, he was released from jail.
Jamie Waylett: Waylett was part of the London riot in 2011. He was then sentenced to 2 years of imprisonment. At the time of his arrest, he was also found to be in possession of marijuana and Molotov cocktail.