Andy Greenwald is joined by Bill Simmons to discuss “Flip,” the series finale of ‘The Larry Sanders Show.’ They start by talking about why it’s one of HBO’s most underrated shows, why Garry Shandling was the perfect fit for the lead role, and how the ’90s comedy blurred the lines between fiction and reality (2:00). Along the way, they discuss the ways in which it was a tortured production behind the scenes and how it influenced the next wave of workplace sitcoms (25:25). Later, they break down the final season’s heightened stakes leading up to the finale (39:40). Finally, they answer the titular question: “Did it stick the landing?” (87:27).

Host: Andy Greenwald

Guest: Bill Simmons

Producers: Kaya McMullen and Kai Grady

Theme Song and Other Music Credits: Giancarlo Vulcano

Learn more about your ad choices. Visit podcastchoices.com/adchoices