Comedian and actor Jim Gaffigan stops by to discuss the long and painful journey to a career in the entertainment industry, from studying finance at Georgetown, to taking improv classes so he can overcome his fear of speaking in meetings at the advertising agency where he worked, to falling in love with stand-up and watching everyone else in his comedy class find success before he did. Jim talks why failure is such a great teacher, getting lost in other people’s expectations, the creepy thing about doing press, and why he doesn’t want power. In his new movie, American Dreamer, he gets the chance to play against type with a complex character in a disturbing thriller, and he shares how he could relate to the delusions of his character, the American fantasy of the “quick fix,” and the rewards of being able to explore a dark character. He and Bridget marvel at Joe Rogan’s abilities, commiserate over the repressed rage of comedians, and reflect that more dangerous than cancel culture, is the growing trend of leaving people out of the discussion altogether.

Full transcript available here: WiW49-JimGaffigan-Transcript