20. The trouble with Paris
Considering Paris Hilton has had more scandalous years in the past (remember that sex tape?), 2006 was a relatively mild year for the socialite (if you call a charge of suspicion of driving under the influence a mild incident, that is). In September, Hilton was charged with DUI suspicion after being pulled over by the police and failing a field sobriety test. Ironically, only three months later, her counterpart Nicole Richie would be arrested for the same charge. It seems those girls really do do everything together.
(Text by James Duffy, Boston.com Correspondent)