#60: Paris Hilton Goes To Jail

by VH1

Paris Hilton parlayed a sex tape and general dim-wittedness into something approaching a career, assuming “showing up” can be considered a job title. But the heir mattress had a bad habit of driving herself around, usually while tanked up.

In February 2007, Hilton was already on probation for a 2006 DUI arrest when she got pulled over for speeding. Police discovered she was driving with a suspended license, and Hilton was eventually sentenced to 45 days in jail for violating her probation.

America’s monosyllabic sweetheart had barely been in jail long enough to be made Big Mama’s bitch when an L.A. county sheriff reassigned her to 40 days home confinement. Even E! channel devotees were suddenly muttering about “special treatment.”

Thankfully, cooler heads prevailed. The day she was due to be begin her confinement, a judge sent her straight back to LA’s Century Regional Detention Facility. Hilton freaked out in court (“Mom, it’s not fair!”) and was hospitalized for a few days before she went back to prison. Thanks to “good behavior”, she wound up serving only 23 days. — Charles Bottomley