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Craft, Bombs, And Building A Comedy Career W/Charlie Cantrell
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A high school writer with jokes that didn’t fit the rubric found a mic, a room, and a path. Charlie Cantrell joins us to pull back the curtain on how a careful craftsman became a working New York comic—without losing the nerve to bomb, pivot, and grow. We talk about the early days at the venue on 35th Street, where five-dollar Thursdays and honest tags turned rough ideas into real sets. From there, Charlie walks us through Hampton Roads to Manhattan, why comics often commit to a few rooms instead of chasing every stage, and how the right environment accelerates timing, cadence, and confidence.
The craft talk goes deep. Charlie once timed every joke and kept binders with a table of contents; now he mixes that structure with improv to work premises live and find the laugh in the moment. We compare “good laughs” that survive weekends to “bad laughs” that only pop in smoky bar chaos, and we trade war stories about hecklers, empty Sundays during football season, and the weird humility of having your dad drive you to a hostile open mic. It’s the unglamorous part of comedy that builds a resilient voice: data from failure, trust earned onstage, and a thicker skin for the next rep.
We also explore influence and evolution. Conan O’Brien’s silly-smart elasticity, Gary Shandling’s authentic introspection, Chris Rock’s sharp angles, and Bill Burr’s shifting POV inform how Charlie structures bits and paces stories. That leads to today’s big question for working comics: when do you burn an hour? We dig into specials, 30-minute formats, and the strategy of building a second hour before releasing the first. Along the way, Charlie shares what acting and improv added to his toolbox—listening, presence, and the freedom to stop chasing a laugh every ten seconds.
If you’re chasing stand-up, curious about the New York scene, or just love hearing how jokes become sets that actually work, this one’s for you. Hit play, then tell us your favorite comedy special and why it still holds up. Subscribe, share with a comic friend, and leave a review so more folks can find the show.
Support the show
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By Jerome Davis
4.9
3232 ratings
Send us a text
A high school writer with jokes that didn’t fit the rubric found a mic, a room, and a path. Charlie Cantrell joins us to pull back the curtain on how a careful craftsman became a working New York comic—without losing the nerve to bomb, pivot, and grow. We talk about the early days at the venue on 35th Street, where five-dollar Thursdays and honest tags turned rough ideas into real sets. From there, Charlie walks us through Hampton Roads to Manhattan, why comics often commit to a few rooms instead of chasing every stage, and how the right environment accelerates timing, cadence, and confidence.
The craft talk goes deep. Charlie once timed every joke and kept binders with a table of contents; now he mixes that structure with improv to work premises live and find the laugh in the moment. We compare “good laughs” that survive weekends to “bad laughs” that only pop in smoky bar chaos, and we trade war stories about hecklers, empty Sundays during football season, and the weird humility of having your dad drive you to a hostile open mic. It’s the unglamorous part of comedy that builds a resilient voice: data from failure, trust earned onstage, and a thicker skin for the next rep.
We also explore influence and evolution. Conan O’Brien’s silly-smart elasticity, Gary Shandling’s authentic introspection, Chris Rock’s sharp angles, and Bill Burr’s shifting POV inform how Charlie structures bits and paces stories. That leads to today’s big question for working comics: when do you burn an hour? We dig into specials, 30-minute formats, and the strategy of building a second hour before releasing the first. Along the way, Charlie shares what acting and improv added to his toolbox—listening, presence, and the freedom to stop chasing a laugh every ten seconds.
If you’re chasing stand-up, curious about the New York scene, or just love hearing how jokes become sets that actually work, this one’s for you. Hit play, then tell us your favorite comedy special and why it still holds up. Subscribe, share with a comic friend, and leave a review so more folks can find the show.
Support the show