Celebrities’ Best Get-Out-Of-Jail-Free Cards


It wasn’t bullet wounds, drug arrests, or trying to single-handedly revive rap-metal — no, an ornery cracked tooth has taken Weezy temporarily out of the game, pushing back his sentencing in attempted weapons possession charges to the beginning of next month. Emergency oral surgery isn’t the only questionable excuse celebs have used to put off or get out of prison; check out some of the best (or worst) after the jump.

Foxy Brown

The pint-sized rapper tried to get an early release from her probation violation sentence due to a malfunctioning hearing aid. The judge denied her request for emergency repair at a clinic in California, but she was still released a bit early for good behavior.

Khloe Kardashian

The least popular Kardashian sister lasted only three hours behind bars for a DUI-related parole violation. Initially the reason given was “overcrowding,” but Kardashian sensationally claimed later that bomb threats targeting her made her presence in the prison a risk to the other prisoners. An impressively self-important move.

Nicole Richie

Before her sentencing for a DUI conviction, rumors swirled that Paris’s ex-BFF got pregnant to avoid jail. Either way, she only served 82 minutes of her sentence, again ostensibly due to overcrowding, and gave birth to Harlow Madden six months later.

Paris Hilton

Just two days into the airhead heiress’s forty-day sentence for a DUI, Hilton was reassigned to home — or in her case, mansion — due to an “unspecified medical condition.” Unfortunately for Hilton, the reprieve lasted only one night before she was carted back to the big house, where she served only twenty-three days.

Pete Doherty

Though the number of celebs that have avoided prison by going to rehab is legion, only Pete Doherty has made it into an art, with the number of times he has been able to weasel his way out of a full sentence with another short stint in rehab or with another anti-drug implant. In January, he even managed to get away with just a fine for “accidentally” bringing heroin to court while in treatment for drugs.


You can’t fault T.I. for not being a nice guy. Rather than trying to shirk his 1000 hours of community service given as part of a reduced sentence for felony gun charges, he used his celebrity prowess to warn teens against violence. Of course, the fact that the MTV reality show following this quest kept his face on TV couldn’t have hurt his career. During a previous stint behind bars, he somehow managed to shoot a music video, and was shortly thereafter moved to a work release program. T.I., the perennial prison overachiever.

And finally, the most impressive (and final) way to avoid prison:

Sid Vicious

After being released from prison on bail for Nancy Spungen’s murder, the Sex Pistol fatally overdosed at a party celebrating his freedom. The heroin was supplied by his mother.