A Conversation with Comedy Writer Dion Flynn

From the ALONG THE SEAM podcast

In 2023, I became part of the inaugural class for the Us@250 fellowship with New America. That fellowship brought together professionals from different disciplines who are all working on projects that speak to the 250th anniversary of the United States, which will be commemorated next year. I was accepted into that fellowship for my work with the ALONG THE SEAM podcast and through that experience had the chance to meet some very inspiring people, including comedy writer Dion Flynn who I am introducing you to today.

Dion is a writer, performer and producer on The Tonight Show Starring Jimmy Fallon, as well as an educator and army veteran. He's known for his many characterizations and songs on the show and even played Barack Obama for over a decade. He also started and runs The Improvisor’s Mindset which is a workshop that provides a safe space for connection, enhancing confidence, rapport building, cultivating creativity and collaboration.

Dion generously joined me in June 2024 to speak about his work and the life that brought him to where he is today. In this conversation, Dion talks about his family life, his recovery, and his one-man show titled, The Only Brown Kid in the Trailer Park. We dig into the importance of laughter, play, and meditation in the service of healing and personal growth.

You can listen to the episode wherever you get your podcasts by searching ALONG THE SEAM, or right here. The transcript for our conversation is below, along with links to clips of his work. (Please note: these transcripts are edited for brevity and clarity, and for paid subscribers. But the podcast episodes are always free for all. You can find a full list of episodes at www.alongtheseam.com)

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