The comedian: Bill Maher

The straight man: ABC

The collision: Bill Maher is known for his say-anything-piss-everyone-off political commentary, but on September 17, 2001, (yes, just six days after the infamous DAY), he went too far for a sizable chunk of America when he followed up a comment about how terrorists aren't cowards with this statement: "We have been the cowards lobbing cruise missiles from 2,000 miles away. That's cowardly. Staying in the airplane when it hits the building, say what you want about it, it's not cowardly." The show was called "Politically Incorrect" so nobody should have been shocked, but FedEx and Sears pulled their ads and ABC canceled the show several months later. (SAM JONES / HBO)