Marion Barry was re-elected twice as mayor of Washington and served for almost 10 years before an infamous 1990 FBI sting operation caught him smoking crack cocaine with a former girlfriend turned informant. Footage of the drug bust and his infamous reaction "Bitch set me up" drew tremendous media attention, as did the ensuing trial.
After serving a six-month sentence, Barry made a surprising return to politics; in 1992 he ran for and won a city-council seat under the slogan, "He May Not Be Perfect, But He's Perfect for D.C." And he didn't stop there. In 1994 Barry won a fourth term as mayor; while he chose not to run for a fifth, he was re-elected to the city council in 2004, a position he has held ever since, despite a guilty plea to misdemeanor tax-fraud charges in 2005 and a July 2009 arrest for allegedly stalking a former employee. Barry's Lazarus-like career inspired a HBO documentary in 2009, fittingly titled The Nine Lives of Marion Barry.