In this unfiltered episode of the Spout Podcast, Emmy-winning actor and stand-up comedian Jeremy Piven joins Erik Zachary for a deep—and often hilarious—conversation about transformation, tenacity, and the art of reinvention. Known for his iconic role as Ari Gold on Entourage, Jeremy opens up about life on the road as a stand-up comic, the grind of handing out flyers despite a Hollywood résumé, and why he’s finally ready to tape his first comedy special in his hometown of Chicago.

He reflects on growing up in a legendary Chicago theater family, his late mother’s profound influence on his craft, and what it’s like to run “Ari Gold lines” with your mom in the room. There are stories about everything from bombing bits to almost winning an NAACP award (yes, really), and a behind-the-scenes look at his most challenging film role yet.

Funny, raw, and full of gems, this one’s for the dreamers, the grinders.

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