Comedian Chris Fleming stops by to talk with writers Mike Sweeney and Jessie Gaskell about trying to make earworms in his comedy music videos, creating the web-series Gayle after moving to LA, what inspired his androgynous fashion, taking a bus from Boston to New York as a teenager for 2 minutes of stand-up stage time, and being heckled by a college mascot into doing a dance-off during one of his stand-up gigs.

 

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Chris Fleming

Conan writers Mike Sweeney and Jessie Gaskell are giving listeners the inside story on some of Conan’s most iconic late-night moments, stretching from his 1993 debut on NBC’s Late Night to his recent CONAN on TBS finale. Starting from the very beginning, they’ll speak with some of Conan’s most iconic guests, writers, and the man himself.

We’ve got all kinds of great stories this season - like that time Conan got in hot water with the government of Finland, or how the Late Night team helped Jack McBrayer land 30 Rock. Other guests include Masturbating Bear creator Brian Reich, former intern Vanessa Bayer, even Liza Powell O’Brien shares what it was like to meet her future husband on a remote involving a chainsaw. Subscribe now!

Comedy

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-centric segment, and the tease of a special surprise narrator.

Conan O’Brien Must Go Writers Roundtable

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 Late Night.

Conan O'Brien & Jeff Ross Return

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.

Jim Gaffigan Revisits The Origins of Pale Force

Mike and Jessie answer some of our listeners' most burning questions about the origins of classic Late Night comedy bits like In The Year 2000 and Jeremy and Ira-Two Guys From Another Dimension. Then David Hopping drops into the studio to discuss stepping in as Conan's successor and reveal a few details about the most mysterious Team Coco employee, Erica Brown.

Listener Questions (Feat. David Hopping)

Actor, comedian, and writer Sam Richardson joins Mike and Jessie to discuss traveling to Ghana with Conan, getting his first taste of Improv in Detroit, and how he and Tim Robinson found each other. Plus, Mike and Jessie are joined by long time CONAN Script Supervisor John Crotteau to talk about the ups and downs of living on a tour bus for the Legally Prohibited Tour, why he's called the Conan whisperer, and the last season of CONAN at Largo.

Chris Fleming

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