Britney Spears
Britney has gone from pop princess to desperately sad pseudo star. Her performance at the MTV VMA's was so shameful that all records of it have been purged from sites such as YouTube. Then of course there's the genital exposure, the imminent loss of custody of her two boys, and her inability to select a dress that actually covers her posterior to add into the mix as well.
Lindsay Lohan
Lindsay has managed to clock up two DUI's, two cocaine possession charges, and several hours in custody in the last year alone. She went to rehab after the first DUI, but reportedly spent her time there simply mixing gases with cough mixture in order to get high. She's a inventive trainwreck, and that gets her the number two spot.
Amy Winehouse
Amy, oh dear Amy. She shot to fame with lyrical claims about not wanting to go to rehab, then went out of her way to prove that she needed rehab worse than anybody else on the planet. The high point came when she overdosed on Ketamine, Cocaine, Vodka, Exstacy, and a few other substances, nearly died, and was then caught just a day or two later preparing to shoot up Heroin in her hotel room with a prostitute.
Paris Hilton
Paris went to jail this year in a shock decision that caused ripples in the very fabric of society and made it into news shows across the world. She served several weeks in jail, and managed to survive even in the face of overwhelming claustrophobia and a sense that the whole thing was rather unfair. When compared to other celebrity sentences, it really was.
Nicole Richie
Nicole managed to get herself a DUI conviction as well as a baby on the way this year. In spite of the fact that she keeps getting in trouble, she served only 82 minutes in prison, thereby making Paris Hilton look positively Mandela-esque in her time served.
