The collision: Performing at the annual White House Correspondents Dinner in April 2006, the faux-conservative Comedy Central host delivered a routine that was sharply critical of both George W. Bush, who sat a few seats away from Colbert at the head table, and the media. Bush did not appear amused, but it was the media who initially wrote off Colbert’s routine as not funny before the public convinced them otherwise. The following year, impressionist Rich Little delivered a not-so-searing routine in which he told some Ronald Reagan jokes. (Mandel Ngan / AFP / Getty Images)
The straight men: New York Dist. Atty. Frank Hogan and New York Archbishop Francis Cardinal Spellman
The collision: Bruce’s blue material raised eyebrows from coast to coast. He had been arrested on obscenity charges before, in San Francisco, Los Angeles and Philadelphia. But it was in New York City that the city government and the church collaborated to put the comedian on trial. After a six-month trial, he was found guilty of obscenity and sentenced to four months in a workhouse. (Kitty Bruce / Shout Factory)