Jessie Gaskell
Jessie Gaskell is a comedy writer and performer.
Guest Appearances
May 21, 2025
Conan is joined by Conan O’Brien Must Go writers Mike Sweeney, Jessie Gaskell, and Jose Arroyo to for a deep dive into how they secured the most iconic scenic shots and accidentally picked up random tourists during their visit to Austria.
May 14, 2025
Conan sits down with writers Mike Sweeney, Jessie Gaskell, and Jose Arroyo to discuss shooting Conan O’Brien Must Go in New Zealand, being joined by Taika Waititi at the record-breaking haka, meeting Conan’s New Zealander name twin, and more.
April 17, 2024
Conan sits down with writers Matt O’Brien, Jessie Gaskell, and Jason Chillem 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.
June 28, 2022
Conan O’Brien and longtime executive producer Jeff Ross join writers Mike Sweeney and Jessie Gaskell to discuss Conan and Jeff’s first meeting, the start of Late Night, Tom Hanks’ message to Conan, and the fate of Conan’s Ford Taurus.
October 27, 2021
Mike Sweeney and Jessie Gaskell join Conan to discuss the upcoming third season of Inside Conan: An Important Hollywood Podcast while they share favorite bits from the early days of Late Night and test Conan’s memories of sketches long gone by.
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March 31, 2019
Conan O’Brien’s made 25 years of late night TV (and counting!). You probably know the support of a staff made that possible. But did you know it also took sprinting, packeting, Schwarzenegger-tracking, Central American kidnapping, index card pouch crafting, and more wild elements all coming together to make ‘Conan’ and its forerunners the comedy institution they are today?
Answer: you did not know that, until you heard this episode of The Cracked Podcast! Alex Schmidt is joined by the multitalented Jessie Gaskell and Mike Sweeney: comedians, writers for ‘Conan’, and hosts of ‘Inside Conan: An Important Hollywood Podcast’. They’ll dive into how they got started, how late night shows function day to day, and surprising stuff from behind the scenes that you’d never know from watching at home. Plus: stick around and click through for a slew of insanely funny characters, sketches, and more that make this one of our funniest footNOTES sections in Cracked Podcast history.
Footnotes: https://www.cracked.com/podcast/17-surprising-tales-from-inside-conanE28099s-late-night-shows