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- As the Civil War rages on, U.S President Abraham Lincoln struggles with continuing carnage on the battlefield as he fights with many inside his own cabinet on his decision to emancipate the slaves.
- Jay marks the debut of his prime time series. After the monologue, Jay welcomes correspondent Dan Finnerty of the Dan Band, who appears in a taped segment singing to a car wash customer. Guest Jerry Seinfeld holds a conversation with Oprah Winfrey and talks about his upcoming reunion with the "Seinfeld" cast on "Curb Your Enthusiasm." Jay shows a spoof of an interview with Barack Obama. Jay talks to Kanye West about West's outburst at the MTV Video Music Awards the previous night, after which West performs with Jay-Z and Rihanna. Jay closes the show with "Headlines."
- Michael Moore appears as a guest to promote his film "Capitalism: A Love Story," Tom Cruise and Cameron Diaz appear in a ten-question interview via satellite, and correspondent Jim Norton does a comedy routine.