The Most Famous Celebrity Jailbirds

Last week's sentencing of Lindsay Lohan marked yet another instance of a high-profile celeb trading in designer duds for an orange jumpsuit. Here are eleven of the most famous celebrity incarcerations (past, present, and pending), including that of the Mean Girls and Freaky Friday actress.

1. Lindsay Lohan - The paparazzi-plagued actress was sentenced to 90 days in prison for violating her probation in a 2007 drug case. The former child star, who is currently shackled to an ankle monitor, has been ordered to surrender on July 20, 2010.

2. Charlie Sheen - Scandal-ridden Sheen was arrested late last year for a domestic dispute. In June, he pleaded no contest to third-degree misdemeanor assault, which gave him 17 to 30 days in jail-a sentence he has yet to serve.

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3. Lil' Wayne - The "Lollipop" singer is currently serving a one-year stint at Rikers Island for illegal gun possession. For 50 cents an hour, the megastar rapper performs suicide watch and socializes with at-risk inmates.

4. Michelle Rodriguez -
In 2008, the Lost star (shown below) served hard time for all of 18 days for violating her probation on previous drunk driving and hit-and-run offenses.
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5. Paris Hilton - The heiress was sentenced for 45 days at a medium-security correctional facility in 2007 for driving with a suspended license. The celebutant-who spent most of her incarceration medical ward for an "unspecified medical condition"-was released just five days into her sentence.
6. Nicole Richie - Shortly after her former BFF, Paris Hilton, was sent to the slammer in '07, Nicole Richie served 82 minutes of her four-day jail sentence. At the time of her brief imprisonment, the reality TV star was five months pregnant with her first child.

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7. Tom Sizemore - The actor, who has struggled with a methamphetamine addiction for the better part of two decades, was thrown into the slammer in 2007 for 16 months-a sentence which was later cut in half. The Saving Private Ryan and Black Hawk Down actor joined ex-girlfriend Heidi Fleiss in the latest season of Celebrity Rehab with Dr. Drew.

8. Kiefer Sutherland - The 24 star's partying ways caught up with him in 2007, when he was slapped with a 48-day jail sentence for a DUI arrest. The actor-who served out the entirety of his mandated term in Glendale, California-spent his time behind bars performing laundry and kitchen duties, including serving other inmates breakfast, lunch, and dinner.
9. Lil' Kim - In 2005, hip-hop's "Queen Bee" was convicted on three counts of perjury and one count of conspiracy-heavy charges that resulted in a 366-day jail sentence and a $50,000 fine. When recently interviewed, the rapper offered friend Lindsay Lohan words of advice and support, saying that the recently sentenced actress should evaluate everything in her life because there is a purpose to her sentencing.

10. Martha Stewart - After her 2004 convictions on conspiracy, obstruction of an agency proceeding, and making false statements to federal investigators, Martha traded her 153-acre estate for a nine-foot by twelve-foot jail cell for five months.

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11. Robert Downey, Jr. - After a series of drug arrests in the '90s, the Oscar-nominated actor was handed a hefty three-year sentence in 1999 for violating probation from a previous conviction. The actor, who famously explained his addiction as "It's like I've got a shotgun in my mouth, with my finger on the trigger, and I like the taste of the gunmetal" has since beat it to again become one of Hollywood's leading men.

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Reprinted with permission of Hearst Communications, Inc.
Mugshots via The Smoking Gun
Image via, via Rueters,