Woody Allen discusses his life and art, the influence of both success and failure on his work, and how he finds comedy in life’s difficulties and trials. He discusses his first screenplay, “What’s Up Pussycat?” and other comedians who have influenced the development of his own comedic work, including Mort Sahl, Charlie Chaplin, the Marx Brothers, and George S. Kaufman.

Jules Feiffer and Studs read several of Feiffer's previous cartoons as they discuss his history as a cartoonist and his retrospective on display at the Walton Street Gallery in Chicago. Feiffer discusses his attempt to move away from political cartoons and instead shift focus to social commentary. Feiffer also discusses his play "Elliot Loves", a love story that captures the complications of love and the “gap” between the sexes.