#27 Paris Hilton
Paris Hilton was arrested and charged with driving under the influence of alcohol in September 2006. In January 2007, she pleaded no contest to a reckless driving charge and was sentenced to three years of probation. She was also ordered to pay fines totaling about $1,500.
Fast forward to August 2010, the socialite was again arrested, this time on suspicion of cocaine possession in Las Vegas. To avoid a felony conviction, Hilton pleaded guilty to two misdemeanors. Under the terms of the plea bargain, she was sentenced to one year of probation and 200 hours of community service. She was also ordered to pay a $2,000 fine and complete a drug-abuse treatment program.