About this episode

Michael Kostroff discusses his enduring acting career and the importance of persistence in achieving success.

What does it really take to build a lasting career as an actor? For Michael Kostroff, the answer is persistence. Michael was actually one of the first guests to ever come on this podcast, and throughout this 10th season, you’ll get to hear from a few returning guests as they share lessons and experiences they’ve had since that initial appearance. Known to many audiences from Broadway, national tours, and television, especially his memorable role on HBO's The Wire, Michael shares the winding path of a career that has spanned decades. From his first professional contract at the Lawrence Welk Dinner Theatre to what he jokingly describes as having two Broadway debuts, Michael reflects on the opportunities, disappointments, and unexpected turns that shaped his journey. He also shares the story of landing a role in the new Broadway production of Dog Day Afternoon at the exact moment he was preparing to move his life to Canada. The conversation also revisits one of the defining experiences of Michael's career: the first national tour of The Producers. He explains why playing Max Bialystock became one of the most challenging and rewarding roles of his life, and how persistence over the…

People in this episode

Host: Patrick Oliver Jones

Guest: Michael Kostroff

Topics covered

• acting career
• persistence
• Broadway
• television
• performing arts

Keywords

• acting
• career
• Broadway
• The Wire
• Dog Day Afternoon
• The Producers
• persistence
• performer

Mentioned in this episode

Organizations: WINMI Media

Books & works: The Wire, Dog Day Afternoon, The Producers

Places: Canada, Lawrence Welk Dinner Theatre

More episodes of Why I‘ll Never Make It

• FINAL FIVE: New York Theater Company with Katherine Winter, Josh Zacher, and John Kroft · July 3, 2026 · 27 min
• New York Theatre Company Takes Performance Off the Stage and Into the Streets · June 24, 2026 · 1h 31m
• FINAL FIVE: Michael Kostroff, Actor in Dog Day Afternoon · June 19, 2026 · 13 min

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