May 2022

Kimmy Gatewood Revisits Her Many CONAN Sketches

Actress, writer, and director Kimmy Gatewood (GLOW, Atypical) joins Mike Sweeney and Jessie Gaskell to discuss her many appearances in CONAN sketches, acting with George R.R. Martin, her hilarious interaction with Orlando Bloom behind the scenes of CONAN at Comic Con, and why she ... Show More

55m 15s

May 2022

Producer Jason Chillemi Revisits Classic CONAN Remotes

Jason Chillemi (the man who made all of our favorite Conan remotes possible) joins writers Mike Sweeney and Jessie Gaskell to discuss the classic Ice Cube and Kevin Hart remotes, the early days of CONAN in Los Angeles, what it was like filming Tom Cruise and Conan in London, and ... Show More

53m 13s

Apr 2022

Matt O’Brien & Meghan Sinclair Revisit Their CONAN Romance

Head writer Matt O’Brien and show photographer Meghan Sinclair join Mike Sweeney and Jessie Gaskell to discuss their courtship at 30 Rock, the early days of CONAN on TBS, chasing Gary Busey with a blimp, and explaining to their kids why Dad is in a Batman porno sketch.Got a quest ... Show More

1h 6m

Dec 2021

Andy Richter Revisits His Early Days at Late Night

Andy Richter joins writers Mike Sweeney and Jessie Gaskell to discuss his early promotion from writer to sidekick at Late Night, how to respond when Conan serenades you in the office, dealing with negative reviews, and a great Shelley Winters story. Got a question for Inside Cona ... Show More

1h 19m

Feb 2022

Steven Wright Revisits His Late Night Appearances

Legendary comedian Steven Wright joins writers Mike Sweeney and Jessie Gaskell to discuss Conan’s skills as an improviser, giving one word answers on Late Night, the crazy coincidence that led to his big break on The Tonight Show with Johnny Carson, and the freedom of couch appea ... Show More

49m 16s

Jul 2019

Andy Richter

Comedian Andy Richter feels just fine about being Conan O’Brien’s friend. Andy sits down with Conan to talk about their 26 years of friendship, how funny and gross the human body can be, using the early internet to pull pranks at work, the advances of plastic surgery over the yea ... Show More

46m 20s

Aug 2023

Conan O'Brien & Jeff Ross Return

Conan O’Brien and longtime executive producer Jeff Ross join Mike and Jessie to continue the origin story of Late Night, including auditioning bands, the terror of the first test shows, the impetus for the first cold open, and the original name Conan and Robert Smigel wanted for ... Show More

1h 16m

Mar 2022

Steven Ho Revisits Beating Up Conan (Many, Many Times)

Martial artist and stuntman Steven Ho joins writers Mike Sweeney and Jessie Gaskell to discuss almost breaking Conan’s leg with a wooden plank, the violent advice he received from Judd Apatow, coordinating stunts on the “Conan vs Andy: Dawn of #ComicCon” sketch, and why he was he ... Show More

55m 30s

Nov 2020

Skyler Higley

Comedian and Conan writer Skyler Higley talks with writers Mike Sweeney and Jessie Gaskell about his experience working remotely from Chicago as a new Conan writer, what it’s like pitching ideas in the room at The Onion, moving to Chicago from Utah to pursue comedy, and pitching ... Show More

38m 11s

Jul 2024

Andy Daly Returns

Actor and comedian Andy Daly feels loud about being Conan O’Brien’s friend. Andy sits down with Conan to discuss his favorite bits and characters from the late night days, the moment in the Peter Pan stage show that changed his life, his quest to buy a Bonanza Steakhouse, and mor ... Show More

1h 10m

May 2020

Conan O’Brien

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.

1h 39m

Apr 2024

W. Kamau Bell Returns

Comedian, director and producer W. Kamau Bell feels insistent about being Conan O’Brien’s friend. Kamau returns to chat with Conan once more about the weapons they’re allowed to keep in the house, the best video essays on YouTube, working as a correspondent on What Would You Do?, ... Show More

1h 2m

Jun 2024

David Oyelowo

Actor, director, and producer David Oyelowo feels winningest about being Conan O’Brien’s friend. David sits down with Conan to discuss playing Coriolanus at the National Theatre in London, attending boarding school in Nigeria, and serving up something authentic with his new seri ... Show More

1h 4m

Andy Richter Revisits His Early Days at ...