EP. 140 — Jake Gyllenhaal

Actor Jake Gyllenhaal feels so many things about being Conan O’Brien’s friend.

Jake sits down with Conan to talk about kindness in entertainment, shooting his new film The Guilty on a contained set, and why performance is so integral in maintaining mental health. Plus, Conan and Sona offer words of encouragement to Matt Gourley as he prepares for impending parenthood.

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February 2, 2025

EP. 327 — Kaitlin Olson

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Actress Kaitlin Olson feels apprehensive about being Conan O’Brien’s friend.

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January 29, 2025

EP. 10223 — One Ring To Rule Them All

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January 26, 2025

EP. 326 — Ben Stiller Returns

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Actor and filmmaker Ben Stiller feels…hmmm…about being Conan O’Brien’s friend.

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