Chase discusses the challenges of mapping out 13-episode arcs and balancing the darkness of the comedy with the drama of the subject matter. At the same time, he and other writers admit to drawing on personal experiences to inform the characters. The cast shares their memories of the late James Gandolfini, his generosity and genius, and how he struggled with being in the spotlight. Chase talks about the enduring love for Tony Soprano's character and the show's circularity from the first episode leading up to the controversial finale.

David Chase recounts his early life in New Jersey, his fascination with filmmaking, and his break into television writing in Los Angeles. After a successful career as a network TV writer, Chase decides to write something personal about his mother.  That becomes "The Sopranos," a feature film about a mobster whose mother plots to kill him. Rejected by the major networks, Chase finds success at HBO for his pilot about a mobster suffering mental breakdowns and starts the casting process for "The Sopranos" as a series. Lorraine Bracco is the biggest name to join as Dr. Melfi and Chase casts the untested musician Steven Van Zandt in a pivotal role. With James Gandolfini and Edie Falco in place, the series films on location in New Jersey, and the unconventional show becomes a water-cooler sensation, despite having an anti-hero as the lead character.