Comedian David Steinberg sits down with two of the greatest stand-ups of all time, Don Rickles and Jerry Seinfeld, for revealing and funny conversations about the craft of comedy. Rickles shares how he perfected the art of the comedic insult, the secrets behind his live shows, his move into film, and his longtime friendship with Frank Sinatra. In a separate backyard chat, Seinfeld opens up about what defines a stand-up comic, his early thoughts on the show Seinfeld, and the discipline behind his humor. The episode also features rare footage of both performing for U.S. Presidents, with Rickles at Ronald Reagan's second inaugural and Seinfeld at a White House tribute to Paul McCartney. It is a true masterclass in timing, wit, and the evolution of stand-up comedy.