Conan O’Brien sits down with Andy Richter on the season finale of The Three Questions to discuss stories from his time at the Harvard Lampoon, writing on The Simpsons and SNL before becoming a late-night icon, and the future Conan envisions for himself.

Conan O’Brien

Host Andy Richter asks the same three questions to each guest: Where do you come from? Where are you going? What have you learned? These three simple questions, when answered honestly and thoughtfully, are enough to provide a pretty complete picture of who a person is. The answers are what Andy always wants to know about people. This will not be a one-sided process, as Andy won’t shy away from getting personal himself.

Comedy

Comedian and writer Jon Lovett, host of “Pod Save America” and “Lovett or Leave It,” joins Andy Richter to discuss balancing comedy and politics, playing Mario on prom night, writing speeches for President Barack Obama, why Jon believes “Late Night with Conan O’Brien” was inherently progressive, some of Jon and Andy’s favorite dad aphorisms, leaving the White House for Hollywood, and more.

Jon Lovett

Actor and podcaster Jake Johnson joins Andy Richter to talk the secret to a good call-in show, the confidence of old men in locker rooms, performing for absolutely no-one, their other names (Mark Weinberger and Andy Swanson), feeling smarter than your teachers in school, laughing at self-serious actors, his path to “New Girl" and "Self Reliance," and much more.

Jake Johnson

Actress and comedian Caitlin Reilly joins Andy Richter to discuss the L.A. transplants that inspire many of her characters, her complicated relationship with social media, why women are more interesting, why Caitlin thinks she may have helped Andy out at her family’s kids clothing store, her dad’s career in soap operas, growing up as the princess of Hancock Park, and much more.

Caitlin Reilly

Actor Jon Cryer joins Andy Richter to discuss his early days in show business, running into each other at the Warner Bros. gym, Jon’s character in “Andy Richter Controls the Universe,” getting dragged into the “first internet sh*t storm,” going to film school boot camp in his thirties, how he ended up playing Lex Luthor, and his new sitcom, “Extended Family.”

Jon Cryer

(Re-released from May 2022) Paget Brewster joins Andy Richter to discuss working on "Andy Richter Controls the Universe" together, not having a plan in showbiz, being a “pilot killer”, working on "Criminal Minds," and more!

Conan O’Brien

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