Host David Steinberg interviews the show business legends, lifelong friends who got their start writing for television variety shows and became comedy motion picture directors, each with a string of classic box office blockbusters to his name.

David Steinberg talks with Don Rickles: they sit on stools in front of an audience. Rickles tells stories, illustrating how he became a comedic insulter, how he plans his shows, the difference between doing stand-up and movies, and his friendship with Sinatra. Steinberg also talks with Jerry Seinfeld, on stools, alone in a backyard. They discuss the nature of stand-up, what makes a stand-up comic, and Jerry's initial take on his TV show. We go back and forth between the two discussions. Also included is footage of both entertaining Presidents: Rickles at Reagan's second inaugural; Seinfeld at a White House evening in honor of Paul McCartney.

Host David Steinberg interviews Curb Your Enthusiasm creator Larry David about his formative years and his choice of comedy over his family's career preference of mailman, the creative struggles of his Saturday Night Live and Seinfeld years, and the influence of Woody Allen on his work.

In the Season 1 finale, series host David Steinberg interviews icons of improvisation. Robin Williams, whose wildly manic standup comedy style was greatly influenced by his mentor Jonathan Winters, off-the-cuff creator of delightfully eccentric characters.

Host David Steinberg interviews a trio of comedy greats about their early encounters with show business legends. Billy Crystal talks about his memories of opening for Sammy Davis Jr., Martin Short recalls meeting Jerry Lewis, whom he has often imitated, and Brad Garrett reveals the innocent joke that got him exiled from opening for Frank Sinatra.

Host David Steinberg talks to a pair of television stars who got their starts in standup comedy but became known for shows that hilariously blended reality and fantasy, pushing the limits of the sitcom format.

Host David Steinberg interviews comedian and actor Chris Rock, who talks about his influences including his minister grandfather and Eddie Murphy, the type of material that plays across all cultural boundaries, his respect for Bill Cosby and Richard Pryor, and his struggle for fame and success in the years after he left Saturday Night Live.

Host David Steinberg interviews a pair of TV comedy superstars with a gift for entertaining live audiences, standup comedienne and talk show host Ellen DeGeneres, and former Carol Burnett Show star Tim Conway.

Host David Steinberg interviews the dryly funny comics whose wickedly smart, subversive observations and twisted takes on the absurdities of everyday life and popular culture have made them household names.

Host David Steinberg interviews comedy actors Steve Carell, who charts the rise of his career from improvisation training to TV and movie stardom; and talks to Carell's 40-Year-Old Virgin costar Jane Lynch, who recalls that her passion for performing and comedy began early, and praises one of her key influences, Carol Burnett.