He'll Sue the Pants Right Off Ya!
Roy L. Pearson Jr. was just your average judge in Washington, D.C. — until a neighborhood dry cleaner misplaced a pair of his trousers. Arguing that he never received "same-day service" or "satisfaction guaranteed" as advertised by the mom-and-pop owners of Custom Cleaners, Pearson sought satisfaction the only way an overeducated lawyer knows how: by filing a $67 million lawsuit against store proprietors Soo and Jin Chung. (He later lowered his demand to $54 million.)
In 2007 a judge ruled in favor of the Chungs, and Pearson walked away with nothing. But that didn't stop him from filing an appeal (which was also rejected). In the end, though, everybody lost. The Chungs had to shutter two of their three stores to finance their defense, and Pearson lost his job four months into the lawsuit after a review board found he lacked "appropriate judgment and judicial temperament."