Today, a visit to the office of legendary director and producer Judd Apatow! We talk about his upbringing in Long Island (5:20), conducting interviews with Jerry Seinfeld and Steve Allen as a teenager (5:46), his move to Los Angeles in the early 80s (17:50) where he befriended a young Adam Sandler and Jim Carrey (21:33), and why he began writing material for other comedians (25:13).

On the back-half, Judd reflects on his start at The Larry Sanders Show in 1993 (28:59), the personal memories he excavated in his 2018 documentary, The Zen Diaries of Garry Shandling (34:13), and the series’ memorable finale in 1998 (39:30). 

To close, we walk through his path from The 40-Year-Old Virgin to Funny People (45:20), his pivot into producing and mentorship (56:47), the legacy of Freaks and Geeks (58:44), and what he hopes to create in the years to come (1:03:27).