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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.

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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 screenwriter and comedian. He is a certified GOGI coach and lead facilitator for AVP (Alternatives to Violence Project). He is the co-founder of Trendsetters, a self-help group aimed to change the culture of prisons. Matt is also an international best selling author for his contribution to Journeys to Success Vol. 7, and he teaches the success principles of Napoleon Hill. He currently writes, directs, and edits for San Quentin Television.
Uncuffed
Stories from inside California prisons