Howard Stern
In 1994, the popular shock jock surprised listeners when he revealed on his radio show that he’d be running for governor of New York as a Libertarian. “It doesn’t matter if you find me offensive,” he announced. “I’ll get out of office before I can really screw anything up.” Promising to reinstate the death penalty and order road construction crews to only work at night, Stern was scorned by the media and eventually dropped out of the race, after refusing to disclose his personal finances.