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Why I‘ll Never Make It

Why I‘ll Never Make It

By: Patrick Oliver Jones
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The actor’s journey is one of occasional highs and frequent lows. It is a path riddled with self-doubt and frustration as we question our career choices, wondering if we’ll ever really ”make it.” But it is those few moments of glory on stage or screen that can sustain us through all the setbacks and challenges. On this award-winning podcast, New York actor Patrick Oliver Jones invites fellow creatives to share three stories that offer a behind-the-scenes look at the creative life rarely seen in the glitz and glam of this industry. These conversations remind us we’re not alone in this often bumpy and winding journey of the performing arts.©2026, WINMI Media Art Entertainment & Performing Arts Music
Episodes
  • FINAL FIVE: Michael Kostroff, Actor in Dog Day Afternoon

    FINAL FIVE: Michael Kostroff, Actor in Dog Day Afternoon
    Jun 19 2026
    Showbiz is full of uncertainty, self-doubt, and surprising moments of joy, a reality that even the most seasoned actors face long after their Broadway debuts. In this episode, celebrated stage and screen actor Michael Kostroff returns for a refreshingly honest and uplifting conversation—no roles, no scripts, just the real story behind his journey in entertainment. Follow Michael: IMDb / IBDB / Instagram Why I’ll Never Make It is an independent production of WINMI Media and Patrick Oliver Jones. To support the ongoing efforts of this podcast please ⁠subscribe⁠⁠ or ⁠⁠donate⁠⁠. Thank you! Learn more about your ad choices. Visit megaphone.fm/adchoices
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    13 mins
  • Michael Kostroff Sees Performing as a Calling and Everyday He Answers That Call

    Michael Kostroff Sees Performing as a Calling and Everyday He Answers That Call
    Jun 12 2026
    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 years has continued to shape him as a performer. Follow Michael: IMDb / IBDB / Instagram --- Why I’ll Never Make It is an independent production of WINMI Media and Patrick Oliver Jones. To support the ongoing efforts of this podcast please ⁠subscribe⁠⁠ or ⁠⁠donate⁠⁠. Thank you! Learn more about your ad choices. Visit megaphone.fm/adchoices
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    53 mins
  • FINAL FIVE: Katerina Papacostas, Chess on Broadway

    FINAL FIVE: Katerina Papacostas, Chess on Broadway
    May 29 2026
    In the previous episode, you heard stories from Katerina Papacostas, where we got into her theater experiences as a 19-year-old as well as her current show, Chess, and filling in for the lead role of Florence Vassy. But there’s more to uncover! And she’s back to answer the Final Five Questions, but first we have an audition story, when Kat was in final callbacks for a Broadway show. And this of course leads us into one my favorite subjects, self-tapes.went in for the role of Nicola in Kinky Boots. -- Why I’ll Never Make It is an independent production of WINMI Media and Patrick Oliver Jones. To support the ongoing efforts of this podcast please ⁠subscribe⁠⁠ or ⁠⁠donate⁠⁠. Thank you! Learn more about your ad choices. Visit megaphone.fm/adchoices
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    32 mins
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