In the Season 1 premiere, series host David Steinberg sits down with legendary insult comic Don Rickles, who reveals the genesis of his act, his inability to do impressions or tell jokes; and with sitcom icon Jerry Seinfeld, who shares his lifelong affection and respect for Rickles and his post-stardom strategy of breaking back into the middle.

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 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.

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 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.

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