S1, E5: As the 2000s unfold, Jay Leno's monologue mastery captivates mainstream America. But his succession struggle with heir-apparent Conan O'Brien is no joke, making waves across the late-night landscape and bringing Jimmy Fallon's fresh voice to the front. Thanks to cable's rise, diverse voices like Chelsea Handler, Andy Cohen and George Lopez get their seat behind the late-night desk, while Jon Stewart and Stephen Colbert take the news into their own hilarious hands.