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

Nov 2021

Writer Brian Reich Revisits Masturbating Bear and Pimpbot 5000

Legendary Late Night writer Brian Reich joins writers Mike Sweeney and Jessie Gaskell to discuss the origins of Masturbating Bear, the literature that inspired Pimpbot 5000, the Late Night office game that involved getting punched in the head, and how he pulled off what is possib ... Show More

1h 7m

Nov 2021

Writer Tommy Blacha Revisits the Gaseous Weiner

Late Night writer Tommy Blacha joins writers Mike Sweeney and Jessie Gaskell to discuss performing as The Gaseous Weiner, the freedom of writing the Satellite TV sketches, and how he gave a Conan line to Dwayne “The Rock” Johnson.Got a question for Inside Conan? Call our voicemai ... Show More

1h 8m

Dec 2021

Brian Stack, Todd Levin, and Brian McCann: An Inside Conan Holiday Special

Brian Stack, Todd Levin, and Brian McCann join writers Mike Sweeney and Jessie Gaskell to discuss classic Conan holiday moments, including Minty the Candy Cane, the Human Centipede Menorah, Conan’s Christmas Ghosts, and more. Got a question for Inside Conan? Call our voicemail: ( ... Show More

1h 8m

Sep 2022

Remembering Brian Reich

Our friend Brian Reich, the legendary Late Night with Conan O’Brien writer responsible for characters like the Masturbating Bear and Pimpbot 5000, passed away on September 12, 2022. We were lucky enough to have him on the show back in November 2021, where he told one of our favor ... Show More

50m 54s

Dec 2020

Frank Smiley & Michael Gordon

Merry Christmas! Writer/producer Frank Smiley & writer Michael Gordon (Conan, Late Night with Conan O’Brien) join writers Mike Sweeney and Jessie Gaskell to talk about helping make the Late Night show different from other talk shows in the early days, the time director Abel Ferra ... Show More

49m 45s

Dec 2020

Brian Stack Returns

Legendary writer/performer Brian Stack (The Late Show with Stephen Colbert, Late Night with Conan O’Brien) joins writers Mike Sweeney and Jessie Gaskell once again to talk about the origin of his character The Interrupter, playing Conan’s creepy gift-giving cameraman, improvising ... Show More

39m 38s

May 2023

Pete Holmes Revisits His Foray Into Late Night Television

Actor, comedian, and author Pete Holmes joins Mike and Jessie to discuss Conan plucking him from obscurity and donning him with a his own Late Night talk show, much like Lorne Michaels did for Conan in 1993 and how that opportunity led to his meeting of Judd Apatow and the eventu ... Show More

1h 30m

May 2024

Paul Scheer

Comedian and actor Paul Scheer feels sanguine about being Conan O’Brien’s friend. Paul sits down with Conan to discuss his new memoir Joyful Recollections of Trauma, creating his own fake video store while at school, awkward celebrity encounters, and working a celebrity imperson ... Show More

1h 3m

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

Feb 2024

Adam Sandler Returns

Actor and comedian Adam Sandler feels sad about being Conan O’Brien’s friend. Adam sits down with Conan once more to discuss the celebrities he’s still nervous to meet, being awarded the Mark Twain Prize for American Humor, the warmest comedians to spend time with, and his new fi ... Show More

1h 1m

Writer Brian Reich Revisits Masturbating...