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.