After near-misses, a L.A. judge ordered the actress to spend 90 days in jail for violating her probation following a 2007 DUI. Lohan’s journey to the big house has seemed inevitable since earlier this year, when the starlet missed alcohol education classes that were a necessary part of her probation. Lohan also skipped a court date due to an appearance at the Cannes Film Festival, claiming her passport was stolen, and was instead ordered to wear an alcohol-monitoring bracelet. Then photos surfaced of Lohan partying after the MTV Music Awards and reports said she had been drinking, although she denied the accusations. Judge Marsha N. Revel listed and more when she said Lohan repeatedly lied to the court and law enforcement. The 24-year-old’s downfall has been well-documented, and although she has been arrested twice for DUI, this is will be her first stint in jail.
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Between 1996 and 2003, the actor had more run-ins with the law than most have in a lifetime. Arrested numerous times on substance-abuse charges, he had several unsuccessful stints in rehab. He explained his relapses in court by claiming that his father, Robert Downey Sr., began giving him drugs when he was eight. In 1999, Downey was jailed for three years after breaking the terms of his parole for a previous drug-related conviction. His lawyer, Robert Shapiro, argued for mercy, claiming that the Oscar nominee was a changed man and persevering in the fight against his addictions. But Judge Lawrence Mira ultimately disagreed saying, “I don’t think we have any alternative [to jail]. We have used them all.” In 2003, after serving his time, Downey successfully turned his life around and has been clean for seven years.
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The hotel heiress was arrested in September 2006 for driving with a blood alcohol level of .08, the minimum required for a DUI arrest. Sentenced to 36 months’ probation and a $1,500 fine, her driver’s license was also suspended, which Hilton found harder to obey. Police arrested her for driving 70 mph a few days’ later and a L.A. judge sentenced her to 45 days in jail. Although she originally promised to appeal, on June 7, 2007, Hilton began her jail sentence at Century Regional Detention Facility, only a few hours after attending the MTV Movie Awards—giving her one of the most glamorous booking photos ever. Hilton, who served 23 days, called the whole ordeal a “traumatic experience” and insisted she got a “raw deal.”
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Does 82 minutes count as hard jail time? Nicole Richie may be one of the only people who can answer that question. Richie was arrested in 2006 after she was pulled over for driving in the wrong lane and told police she had been smoking marijuana and taking Vicodin. But Richie had a record: she had a 2003 DUI conviction, and California law mandates any second-offender must serve a mandatory 5-days in jail. Richie was sentenced to four days in jail in July 2007—by then she was pregnant with her first child with boyfriend Joel Madden. Among a media circus, Richie arrived at the Los Angeles County Sheriff’s Department at 3:15 p.m. for booking and was released by 4:37. Authorities insisted she was treated as any other inmate with a similar sentence, and the short jail stint was because of overcrowding.
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The 24 star was sentenced in 48 days in jail for a 2007 drunk driving arrest. Sutherland, already on probation for a 2004 DUI, had pled no contest so he would serve his time while filming for 24 was on hiatus. Sutherland turned himself into authorities on December 5th, 2007 and spent the next seven weeks in an 8 by 10 cell in Glendale, CA. Although reports trickled out during his stint that he was doing well in prison, Sutherland said after he was released that he “did a lot of folding clothes and thinking about what I was doing in there.” He later joked about the experience with David Letterman, saying that when he dropped soap in the shower, he realized how overrated soap is. Would anyone in jail mess with Jack Bauer? Even over soap? Kiefer Sutherland didn't want to test it.
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Rapper Lil’ Kim was convicted on three counts of perjury and one count of conspiracy in March 2005—a sentence that could have landed her up to 20 years in jail, but she ended up being sentenced to one year and a day. Kim—born Kimberly Denise Jones—faced charges after she testified to a grand jury that she was not present at a 2001 shooting involving her bodyguard, but security footage found later showed her at his side. Kim began her sentence on Sept. 20, 2005, and made her triumphant return to the music scene one year later at the MTV Video Music Awards, where she wore a orange jumpsuit onstage shortly after her release and crowed “the girl is back!” Kim later did a stint on Dancing With the Stars, which she said she watched faithfully in prison. “Me and my girls used to watch it and they would say, ‘You need to be on that show,’” Kim said.
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The Godfather of Soul had plenty of run-ins with the law, but his most famous—and longest prison sentence—stemmed from an alleged drug-fueled high-speed chase in 1988. Police claimed Brown was high on PCP and chased him down on Interstate 20 on the Georgia-South Carolina border. A jury convicted him for carrying a handgun and assaulting a police officer, although Brown always maintained his civil rights had been violated and his then-wife said she had called the FBI for help. According to an FBI report released after his death, the FBI investigated the matter and found that police had shot at and chased Brown without being provoked, and Adrienne Brown had called the bureau to complain about harassment by local cops and said her husband had never used PCP. Brown was released in 1991 after serving three years, although he was arrested several times afterward, including one for domestic violence in 2004 that produced his infamous mug shot.
Track star Marion Jones had for years issued angry denials that she ever took steroids, and even issued filed a $25 million lawsuit against notorious drug company BALCO for alleging she had used a steroid called THR or “the clear.” But by 2008, she tearfully admitted to a federal judge that she lied in a 2003 federal investigation into doping. As a result of her reported steroid use, she was stripped of all her medals and charged with lying to a federal agent. A San Francisco judge sentenced Jones to six months in jail after she pleaded guilty. Jones pleaded for leniency in her sentencing, and she later applied for commutation to President George W. Bush only five days after she started serving her sentence in March 2008. A top official of USA Track and Field wrote an open letter to President Bush discouraging Jones’ request, using the same argument as the judge: that it would send a bad message to young people who had idolized her.
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In 2004, at the age of 63, Martha Stewart was convicted of lying about a stock sale—the selling of 4,000 shares of shares of ImClone stock shortly before the FDA announced its rejection of one of ImClone’s cancer drugs and the price plunged. Stewart was sentenced to the minimum allowed by her conviction by a federal judge, and fined $30,000. Stewart started her sentence in October 2004, saying she would miss her pets, but she hoped to be out by spring gardening. Stewart was released in March 2005 and promptly released a statement where she called the experience “life altering and life affirming.”
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The music producer was convicted in 2009 of second-degree murder in the 2003 death of Lana Clarkson. At the age of 69, Spector was sentenced to 19 years to life, although he’s always maintained his innocence. The New York Post reported in 2009 that Spector received death threats while in prison, and he claimed that he was in the same prison as notorious serial killer Charles Manson, although prison officials denied they were in the same prison. Spector also his said his wife—40 years his junior—made the 800-mile trip to visit him and gave him food so he would not “have to go in to the dining room with the scumbags.”
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Although never convicted in the deaths of his ex-wife Nicole Brown Simpson and Ron Goldman, O.J. Simpson eventually met the inside of a jail cell. After famously being acquitted in the 1995, a civil jury found Simpson liable for their deaths and ordered him to pay $33.5 million. Simpson, though, was arrested in Sept. 2007 for allegedly attempting to steal at gunpoint sports from a Las Vegas hotel room; he said he was trying to reclaim what was rightfully his. Unlike the media circus of his first trial, Simpson was quietly convicted on 12 criminal charges, including kidnapping and armed robbery. A judge sentenced Simpson to the maximum—33 years, a minimum of nine with parole—although she said the sentence had nothing to do with any previous charges. In recent reports, Simpson has said he is “bored out of my mind” in prison, and the football star had taken up baseball.
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The hero of the 2007 Super Bowl, Plaxico Buress probably did not imagine he would be in prison by the 2010 Super Bowl. Buress was arrested in 2008 after he accidentally shot himself in the thigh at a New York nightclub with an unregistered gun. Under New York’s strict anti-gun legislation, he faced a hefty prison sentence and eventually pled guilty to attempted weapons possession and was sentenced to two years in prison. Buress has pledged to return to the NFL when he is eligible for release in 2011, and New England Patriot Fred Taylor, a friend, said in April 2010 Buress remains “in great spirits.”
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The Home Improvement star was not always so squeaky clean. In 1978, Allen was arrested at the Kalamazoo/Battle Creek International Airport for being possession of 650 grams (1.4 lbs) of cocaine. He pleaded guilty, and to avoid life imprisonment, he provided the names of his dealers. He served 28 months in a federal jail. Although later, he told George Lopez there was one perk to prison: a simple dress code. Although Allen seemed to have cleaned up his act, he was arrested again in 1997 for drunk driving, and later went to rehab.
Dwayne Michael Carter Jr. had a handful of brush-ups with the law before he was finally convicted in March 2010 on drug- and firearm-related charges. In January 2008, Lil Wayne was arrested after his tour bus was stopped and searched by Arizona Border Patrol agents, who uncovered a sizeable cache of marijuana, cocaine, and MDMA along with $22,000 in cash in his possession. This arrest ultimately served to add three years probation to his previous arrest in January 2007, when Wayne was arrested in New York after police discovered a .40 caliber piston on his person. Sentenced to a year in prison in March, he is currently serving in Rikers Island correctional facility.
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