Bill Carter speaks with legendary hosts Jimmy Kimmel and Dick Cavett, the genre's newest star Amber Ruffin, Conan O’Brien’s sidekick Andy Richter and many more to dissect one of TV’s hardest, most challenging jobs - the late night TV host. These individuals aren’t just the stars of the show: they’re writers, directors, and crisis managers. While they are everything from charming to difficult, inspiring to insecure, and even downright eccentric, their genius shines bright when they consistently make it all look so easy - five nights a week, every week!

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