Today, we’re joined by comedian Nick Kroll! To begin, we dive into the origin of Little Big Boy, his first stand-up special in ten years (4:40), his pivot toward more personal comedy (7:22), and a bit about mothers and sons (10:30). Then, we walk through Kroll’s upbringing in Rye, New York (13:08), falling in love with comedy at Georgetown University (19:35), and a formative experience chauffeuring actor Harrison Ford (25:30).

On the back-half, we discuss the role of observation in his sketch work (29:40), memorable characters from Kroll Show (31:52), why he continues to evolve his comedy (34:05), a transformative trip to the Galápagos Islands (39:42), lessons learned from fatherhood (41:34), and his hopes in the years ahead (44:15).

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