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."