Chris Brown managed to avoid prison time for assaulting Rihanna in 2009 by taking a plea deal, but ran into trouble while on probation thanks to an October 2013 felony assault arrest in Washington, D.C. He still could have avoided jail time by completing court-ordered stints in an anger management rehab facility and a Malibu, California, treatment facility. While he successfully did his 90 days in the anger management rehab facility, he was kicked out of the second rehab facility in March 2014 for violating rules and sent directly to a Los Angeles County jail. He remained behind bars until he was granted early release on June 2, 2014, due to overcrowing.
Lindsay Lohan has spent between 84 minutes and 14 days on several stints behind bars for violating probation on misdemeanor theft and DUI convictions, being released early each time due to overcrowding.
Former NFL star and "Naked Gun" actor O.J. Simpson is serving a 33-year prison sentence on kidnapping and armed robbery convictions for his role in the September 2007 theft of various sports memorabilia at the Palace Station hotel in Las Vegas. In July 2013, he won parole on some of the convictions, but will still spend at least another four years in prison.
Paris Hilton served 23 days in a Los Angeles County jail in June 2007 for violating her probation in an alcohol-related reckless driving case.
Later that summer, Nicole Richie, Hilton's one-time BFF, served about 82 minutes of a four-day sentence for driving under the influence of marijuana and Vicodin before being released early due to overcrowding.
Martha Stewart famously spent five months in federal prison followed by five months of home confinement between October 2004 and March 2005 for her conviction on charges related to the ImClone insider trading affair.
Legendary music producer Phil Spector, who produced more than 25 Top 40 hits between 1960 and 1965, was convicted in 2009 of second-degree murder in the 2003 shooting death of actress Lana Clarkson in his Alhambra, Calif., home. He is serving a prison sentence of 19 years to life.
Christian Slater spent 59 days in jail in 1998 after assaulting his then-girlfriend and a police officer while drunk and high in 1997.
Robert Downey Jr. had a variety of legal troubles earlier in his career, including spending nearly a year in a California prison in 1999-2000 for breaking his probation for drug charges. In 1997, he also spent 113 days in a Los Angeles County jail for violating his probation on a 1996 drug conviction.
The rapper T.I., whose real name is Clifford Joseph Harris Jr., has twice spent time in prison, stemming from weapons possession, drugs charges and probation violation. He served seven months between May and December 2009, and another 11 months between October 2010 and September 2011.
Before he became famous, "Home Improvement" star Tim Allen spent more than two years in prison after pleading guilty to a cocaine-trafficking charge in 1978.
In 1990, Zsa Zsa Gabor served a three-day jail sentence for slapping a Beverly Hills traffic police officer during a June 1989 traffic stop.
In 2010, rapper Lil Wayne, whose real name is Dwayne Michael Carter Jr., served eight months of a one-year sentence he received for pleading guilty to attempted criminal possession of a weapon.
Rapper Ja Rule, whose real name is Jeffrey Atkins, spent nearly two years in prison from June 2011 to May 2013 for attempted illegal gun possession and tax evasion.
At age 16, Mark Wahlberg assaulted two different Vietnamese men in Dorchester, Mass., on April 8, 1988, shouting a racial epithet at one man and permanently blinding the other in one eye. He was arrested for attempted murder, pleaded guilty to assault, and sentenced to two years in prison. Wahlberg ended up serving 45 days before being released.
"White Men Can't Jump" and "Blade" actor Wesley Snipes was convicted of willfully failing to pay taxes from 1999-2001. He began serving a three-year prison sentence in 2010 and was released on April 6, 2013.
In late 2007, Michelle Rodriguez, known for her roles in movies such as "The Fast and the Furious" and "Avatar," was sentenced to 180 days in jail for violating probation on a 2006 DUI conviction. Like Lohan, Hilton and Richie, she was released early due to overcrowding after serving 18 days. She also spent less than a day in jail on the original 2006 conviction and another 48 hours in jail in 2004 after pleading no contest to hit and run, drunken driving, and driving with a suspended license.
"Machete" star Danny Trejo was in and out of jail and prisons in California as a teenager and young adult during the 1960s. According to a 2010 interview with USA Today, he spent a total of 11 years in the San Quentin and Soledad state prisons on drug and robbery charges, with his last stint ending in 1972.
Richard Hatch, the first "Survivor" winner, was convicted in 2006 of failing to pay taxes on his $1 million in winnings from the show. As a result, Hatch was sentenced to a 51 months in prison. In March 2011, he received another nine months in prison for violating the terms of his release by failing to re-file his 2000 and 2001 tax returns.
Mötley Crüe lead singer Vince Neil spent 15 days in jail after pleading guilty in 2011 to drunken driving in Las Vegas.
After receiving a three-to-nine year sentence for pleading to multiple counts of drug dealing and possession in 1994, a teenaged 50 Cent, the rapper whose real name is Curtis Jackson, was given the option of instead going to a shock incarceration boot camp, where he ended up serving more than six months.
In July 2005, Lil Kim was sentenced to one year and one day in prison after being convicted of three counts of conspiracy and one count of perjury for lying to a federal grand jury about her friends' involvement in a 2001 shooting. She was paroled on Sept. 19, 2006, after serving about 10 months of her sentence.
Boxing promoter Don King was convicted of second-degree murder in 1966 for the stomping death of Sam Garrett, an employee who owed him $600. He ended up serving just under four years in prison after the conviction was reduced to nonnegligent manslaughter. Ohio Gov. Jim Rhodes later pardoned him for the crime in 1983.
"The Godfather of Soul" James Brown was arrested for armed robbery in 1949 at the age of 16 and spend three years in a juvenile detention center. He was also sentenced to six years in jail in 1989 in connection with a September 1988 police chase through two states. He would be released in 1991 after serving nearly three years of his sentence.
"24" star Kiefer Sutherland pleaded no contest to a DUI charge in Los Angeles in October 2007 and served 48 days in jail, with part of that sentence coming for violating his probation for a 2004 drunken driving offense.
Country music legend Glen Campbell spent 10 days in Maricopa County's Tent City jail during the summer of 2004 for a drunken driving conviction, although the last eight days of his sentence he was allowed work release during the day. He even staged a free concert for his fellow inmates during his stay.
Eight-time Grammy-winner Lauryn Hill pleaded guilty in the summer of 2012 to not paying federal taxes on more than $1.5 million earned over three years. She was eventually sentenced to three months in prison and served all but a few days of her sentence, being released for good behavior on Oct. 4, 2013. She also had to pay $970,000 in back taxes and penalties and spend another three months in home confinement.
Boxer Mike Tyson served three years in prison between 1992 and 1995 for raping 18-year-old Desiree Washington, Miss Black Rhode Island, in an Indianapolis hotel room on July 19, 1991.
Actor Tom Sizemore, best known for his roles in movies such as "Heat" and "Saving Private Ryan," spent several months in jail after being convicted in 2003 of assault and battery against his girlfriend, the former "Hollywood Madam" Heidi Fleiss. He then served another six months after a bust for methamphetamine possession in 2007.
Robert Mitchum was arrested for vagrancy at the age of 14 in the early 1930s in Savannah, Ga., and put on a local chain gang. By Mitchum's own account, he escaped and returned to his family in Delaware and later went on to become a Hollywood legend thanks to movies like "The Night of the Hunter" (pictured), "Cape Fear," "Thunder Road" and "The Sundowners."
In December 2012, rapper Fat Joe, whose real name is Joseph Antonio Cartagena, pleaded guilty to tax evasion for not paying income tax on more than $3 million from 2007-2010. He was eventually sentenced to four months in prison, serving his time between Aug. 26, 2013, and Nov. 28, 2013.
Singer Boy George was sentenced to 15 months in jail in January 2009 for falsely imprisoning a male escort. He would end up serving four months of the sentence before being released for good behavior.
Like other celebrities before her, Khloé Kardashian served less than three hours of her 30-day sentence in a DUI case on July 18, 2008, due to overcrowding in the Los Angeles County jail system. She was originally given three years probation for the March 2007 drunken-driving incident, but failed to complete roadside cleanup duty and enroll in an alcohol education class as required by the terms of her probation.