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Crosscurrents

My proudest moment: Stand-up at San Quentin

Matt Sheppard is an Uncuffed graduate and facilitator. He's also a comedian.
Uncuffed / KALW
Matt Sheppard is an Uncuffed graduate and facilitator. He's also a comedian.

This story aired in the July 8, 2025 Crosscurrents episode.

Click the button above to listen!

Uncuffed producer Matt Sheppard has many different talents — he’s working in the prison as an audio journalist and storyteller, and he’s a documentary filmmaker, too. But one of the things that brings him, and others, the most joy? His comedy. Matt shares a story about one meaningful stand-up performance.

This piece was brought to you by the team at Uncuffed. Our work in prisons is supported by the California Arts Council, the Department of Corrections and Rehabilitation, and donations from listeners like you. Content is approved by an information officer.

Follow @WeAreUncuffed on Instagram and Facebook 

Learn more, sign up for Uncuffed news, and support the program at www.uncuffed.org

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Crosscurrents From The Producers Of UncuffedPersonal Stories
Matt Sheppard is a graduate of The Last Mile’s Audio/Video program and is an award winning film producer. His film Dying Alone is currently being played in the SF MOMA. He was a lead producer and facilitator for the award-winning Uncuffed podcast and audio storytelling program. On August 18, 2026, after 24 years of incarceration, Matt paroled from San Quentin. Now that he is free, he plans on pursuing careers in radio, filmmaking and comedy.