Apr 2024

Conan O’Brien Must Go Writers Roundtable

Conan sits down with writers Mike Sweeney, Matt O’Brien, Jessie Gaskell, and producer Jason Chillemi for a roundtable discussion about the making of his newest travel show Conan O’Brien Must Go, featuring insights into the destination selection process, a sneak preview of a Bono- ... Show More

15m 32s

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

Jul 2023

Jim Gaffigan Revisits The Origins of Pale Force

Comedian and author Jim Gaffigan joins Mike and Jessie to discuss his many stand-up appearances on Late Night and CONAN, the origins of the Late Night cartoon series "Pale Force", and the future of Late Night television as a whole. This episode was recorded on 6/15/2023.Got a que ... Show More

54m 5s

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

Sep 2019

Matt O’Brien, Conan head writer

Conan head writer Matt O’Brien joins Conan writers Mike Sweeney and Jessie Gaskell to talk about the recent writer submission process which included reading over 400 writer submissions, common red flags, and more. Plus, Mike shares a legendary Brian Reich story from the writers r ... Show More

42m 59s

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

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

Jun 2023

Conan Head Writers Roundtable with Robert Smigel, Jonathan Groff, and Matt O'Brien

Robert Smigel, Jonathan Groff, and Matt O'Brien join Mike and Jessie as the head writers from each era of Conan's Late Night shows to discuss their favorite remotes, moments, and disasters from each of their Late Night reigns. Plus, Mike and Jessie breakdown the origins of Nathan ... Show More

1h 26m

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

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

Feb 2022

Ian Roberts Revisits His Baby’s Late Night Debut

Ian Roberts (Uprights Citizen Brigade, Arrested Development) joins writers Mike Sweeney and Jessie Gaskell to discuss injuring himself during a Late Night sketch, working with the legendary Nipsey Russell, his daughter’s performance as a baby in a Conan bit, and the early days of ... Show More

1h 10m

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

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

Writer Brian Reich Revisits Masturbating...