10 Most Pampered Celebrity Prisoners

Celebrities commit the same crimes as regular people, but when they get punished for their wrongdoings, it usually includes a gentler sentencing and a sugar-coated jail experience. Whether it’s because of their fame — some have said that celebrities are not worth keeping in jail for “small-time” charges because their fame level causes too many disruptions — or bribery skills, celebrities can, and often do, live the good life even behind bars. Here’s a look at the 10 most pampered celebrity prisoners:

  1. Paris Hilton

    Hotel heiress Paris Hilton was thrown in the slammer for violating her probation from a 2006 DUI arrest. On June 5, 2007, Paris checked herself into the Century Regional Detention Facility. Two days later, the LA County Sheriff reassigned her to 40 days of home confinement and electronic monitoring because of an unspecified medical condition. But Hilton was sent back to jail to serve her original sentence of 45 days. Hilton’s mysterious medical condition landed her in solitary confinement in the medical wing. Paris received regular visits from her lawyer and psychiatrist while in jail, and reportedly never had a routine cavity search that other prisoners go through.

  2. Lindsay Lohan

    In July 2010, Hollywood bad girl Lindsay Lohan was sentenced to 90 days in jail for violating her terms of probation. Lohan was also ordered to check into an inpatient rehab program after her release from jail. Not only did Lohan get off easy with a short 14-day stay because of prison overcrowding, but she also received preferential treatment behind bars. She continued to receive her usual prescription medications in jail and got to have visitors after official visiting hours. Lohan was also allowed to order food from a special store and could have specific items delivered to the jail that weren’t readily available.

  3. Lil Wayne

    In 2010, rapper Lil Wayne was sentenced to one year in prison for his 2007 gun charges. Lil Wayne’s pampering began before he ever stepped foot in prison. His sentencing was pushed back a month because of a dental surgery. Once admitted to Rikers Island, he was placed in a high-class area to keep him separated from the rest of the prisoners. He had his own cell with a window facing outside. Lil Wayne cooked, watched television, became an Uno champion, and described his 8 months behind bars as “not that difficult.”

  4. O.J. Simpson

    O.J. Simpson may have gotten away with murder, but he’d paid the price for his 2007 robbery that sent him to the slammer. Simpson is currently serving his 33-year sentence at Nevada’s Lovelock Correctional Center. The former football star gets to enjoy watching television in his cell, but has complained about not having HBO. Simpson also plays checkers and cards with his fellow convicts, and gives prison food two thumbs up. Looks like Simpson may be right at home there.

  5. Martha Stewart

    In 2004, domestic diva Martha Stewart served five months at Federal Prison Camp, Alderson in West Virginia, for conspiracy, obstruction of an agency proceeding and making false statements to federal investigators. Stewart stayed busy in prison by scrubbing floors and raking leaves. She exercised by walking around the prison grounds and attended nightly yoga classes. Martha didn’t even fall behind on her gardening or craft projects because she was always picking flowers, crocheting, painting ceramics and making Christmas decorations.

  6. Foxy Brown

    Female rapper Foxy Brown was pampered like a princess during her time at Rikers Island. Brown served nine months for violating her parole after she assaulted two nail-salon manicurists in 2006. While in jail, she was allowed to wear Gucci sneakers, a Fendi scarf and apply makeup. The rap diva had unlimited TV and phone use and had meals delivered to her cell by prison guards. They even helped her set up an interview and photo shoot for a magazine that promoted her new album.

  7. Joe Francis

    In April 2007, Joe Francis, founder of the Girls Gone Wild video empire, was sentenced to 35 days in jail for contempt charges. Francis was admitted to a Panama City, Florida jail, where he was accused of bribery, possession of a controlled substance and introducing contraband into the jail. He allegedly offered a guard $500 for bottled water and had prescription medications in his jail cell. Francis was allowed to keep the medications because they were deemed necessary to his health. According to the sex video mogul, he was “treated like a rock star, a total her” by his fellow inmates.

  8. Plaxico Burress

    Former Giants star Plaxico Burress was sentenced to two years in prison for criminal weapons charges and a single count of reckless endangerment after accidentally shooting himself in the thigh with his own gun at a New York nightclub. Burress checked in at Rikers Island to unpleasant taunts and yells from prisoners, but this football star still got the royal treatment behind bars. Burress was immediately separated from the regular inmate population and given his very own cell. As predicted, Burress’ good behavior will get him an early release from prison on June 6, 2011.

  9. Alexis Neiers

    Alexis Neiers, the star of the television show, Pretty Wild, went pretty wild when she participated in the celebrity “bling ring” robberies and got caught. Neiers was arrested and sentenced to 180 days behind bars at the Century Regional Detention Facility. The 19-year-old managed to escape some of the standard treatment and procedures prisoners typically go through, such as the ever humiliating cavity search. She also only served 30 days of her sentence, and for the last five days, she was held in a cell next to Lindsay Lohan.

  10. T.I.

    On Nov. 1, 2010, rapper T.I. was sentenced to 11 months in federal prison for drug possession charges that violated his terms of probation. The bad boy rapper was admitted to an Arkansas prison where he received some preferential treatment, especially when his wife came to visit. The couple was caught canoodling in a private visiting room outside of the guards’ sight. T.I. has also had the privilege of using prison phones and email liberally.

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