"Like having a three-way with yourself" Heather Leroy on making her first feature episode artwork

EPISODE · Mar 17, 2026 · 1H

"Like having a three-way with yourself" Heather Leroy on making her first feature

from Film Sh!t · host Nate Caywood

Heather LeRoy’s career path doesn’t follow a neat map, and that’s exactly why it’s useful. We sit down as friends and working artists and trace how a kid on a dead-end road in Alabama turns Saturday Night Live obsession into a real creative life: New York acting classes, Emerson film school, Los Angeles stand-up, and eventually a feature film that refuses to play it safe.We get into the messy, practical reality of independent filmmaking and microbudget features. Heather breaks down what happens when a “$25K movie” meets real life: producers quitting mid-shoot, becoming your own producer by necessity, and the constant pressure of writing, directing, acting, and editing with delayed gratification. We also talk about finding your voice, casting smart, and why the best collaborators are the ones who instantly understand the same weird movie you’re trying to make.Then we go past the finish line, because the finish line isn’t real. Heather shares what surprised her most about film distribution, deliverables, and the unglamorous costs like errors and omissions insurance. We also hit the bigger question hanging over every set right now: AI and the future of the film industry. Her take is clear and grounded in craft: technology shifts business models, but it can’t replace human flaws, risk, and connection, which is the whole reason movies matter.If you care about screenwriting, directing actors, DIY filmmaking, mental health storytelling, and getting a film into the world without waiting for permission, this one’s for you. Subscribe for more conversations with working film and TV professionals, share this with a filmmaker friend, and leave a review with the leap you’re taking next.

Heather LeRoy’s career path doesn’t follow a neat map, and that’s exactly why it’s useful. We sit down as friends and working artists and trace how a kid on a dead-end road in Alabama turns Saturday Night Live obsession into a real creative life: New York acting classes, Emerson film school, Los Angeles stand-up, and eventually a feature film that refuses to play it safe. We get into the messy, practical reality of independent filmmaking and microbudget features. Heather breaks down what hap...

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"Like having a three-way with yourself" Heather Leroy on making her first feature

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This episode was published on March 17, 2026.

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Heather LeRoy’s career path doesn’t follow a neat map, and that’s exactly why it’s useful. We sit down as friends and working artists and trace how a kid on a dead-end road in Alabama turns Saturday Night Live obsession into a real creative life:...

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