Why I‘ll Never Make It

Patrick Oliver Jones
  • 4.3 (29)
  • Performing Arts
  • Updated Biweekly

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.

  1. 4d ago ·  Bonus

    FINAL FIVE: Michael Kostroff, Actor in Dog Day Afternoon

    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

    13 min

  2. Jun 12

    Michael Kostroff Sees Performing as a Calling and Everyday He Answers That Call

    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

    53 min

  3. May 29 ·  Bonus

    FINAL FIVE: Katerina Papacostas, Chess on Broadway

    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

    32 min

  4. May 28

    Katerina Papacostas Is Making All the Right Moves in Chess on Broadway

    Broadway performer Katerina Papacostas joins the opening episode of Season 10! She has spent years of working in on tours, on Broadway, and across regional theatre. Currently appearing in the Tony Award–nominated revival of Chess, Kat recently stepped into the lead role of Florence Vassy, filling in for Lea Michele. In this conversation, Kat opens up about the realities of building a sustainable career in the arts — from survival jobs and burnout to leaving New York entirely and eventually becoming a software engineer while still pursuing performance. She shares how redefining success for herself created a healthier and more balanced creative life, both onstage and off. It’s an honest conversation about persistence, reinvention, and what it really takes to stay in the game long enough for opportunities to arrive. -- Why I’ll Never Make It was recently selected by MillionPodcasts as one of the Top 70 Musical Theatre Podcasts on the web (2026 Edition). This podcast 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

    1h 16m

  5. May 1

    A Look Back at Lynn Nottage Shaping Stories That Matter in American Theater

    As actors, it’s easy to get caught up in auditions, roles, and the day-to-day work of performing, often without stepping back to consider the larger forces shaping the stories we’re asked to tell. Playwright Lynn Nottage operates on that larger scale. A two-time Pulitzer Prize winner and one of the most influential voices in American theater, Lynn has built a body of work that challenges audiences while expanding what stories are seen and heard on Broadway and beyond. In this conversation, recorded in 2024, Lynn speaks candidly about the responsibility of storytelling, the discipline behind the writing process, and the long road to trusting a creative voice in an ever-evolving industry. From Ruined, which explores the lives of women during the civil war in the Democratic Republic of Congo, to the Tony Award-winning musical MJ, Lynn discusses the balance between artistry, ethics, and collaboration in theater. What emerges is a clear and grounded perspective on what it means to create meaningful work—not for recognition, but with intention. For anyone working in the performing arts, whether onstage or behind the scenes, this conversation offers a deeper understanding of how stories are shaped, and why the ones that matter most are often the hardest to tell. Follow Lynn: Website / Instagram / IBDB Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 8m

  6. Apr 20

    A Look Back at J. Harrison Ghee & Caroline Bowman Before the Breakthrough Moments

    Identity can feel like a moving target in the performing arts—something shaped not only by the roles actors play on stage, but by the expectations placed on them offstage as well. In this episode, recorded in 2019 at the Muny in St. Louis, J. Harrison Ghee and Caroline Bowman sit down to talk about navigating that balance in a career built on visibility. From starring in productions like Kinky Boots, Evita, and Wicked, both performers share what it means to take on iconic roles while also staying grounded in a sense of self within the world of Broadway, musical theater, and the larger performing arts industry. Looking back now, this conversation captures a moment before major milestones in each career—before Caroline Bowman took on the role of Elsa in the Frozen national tour, and before J. Harrison Ghee won a Tony Award for Some Like It Hot. What comes through is a candid and thoughtful discussion about identity, vulnerability, criticism, and the pressure to fit into categories, both as actors and as people. It’s an honest look at the work it takes to show up fully, take risks, and build a life in theater without losing sight of who you are. Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 28m

  7. Apr 13

    A Look Back at Ann Harada and Finding Longevity as an Actor

    No matter what it is that initially motivates someone to be in the arts, it could be the craft or the people or the fame, there is one thing I think we all strive for: longevity. Besides finding consistent work, which is certainly no small task, the foundation of a long career is figuring out what it takes to personally stay motivated, energized, and still be yourself over the years. Some days it can feel like you’ve got a handle on it, while other days it’s a scramble to keep priorities straight and maintain direction.  I sat down with Ann Harada in 2024 to talk about Broadway career that has spanned 4 decades, from the original production of M. Butterfly and the most recent revival of Into the Woods to her current Broadway show, Schmigadoon.  But Ann would be the first to tell you that finding happiness and satisfaction in the acting business didn’t come quickly or easily for her. In our conversation, she talked about some lean years before Avenue Q made her a Broadway star as well as how she continued working hard and pushing herself both on and offstage.  Follow Ann: Schmigadoon / Facebook / IMDb / IBDB Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 8m

  8. Apr 3

    A Look Back at Adrienne Walker Navigating Rejection as a Broadway Actor

    Rejection is a constant in this business, even when you’ve had success. Some days you take it in stride, other days it can really sink in deeper than you expect. I’ve had plenty of moments where I questioned whether I was on the right path, wondering if I should leave New York or perhaps find another career altogether. At times it has been a real challenge to balance hope with reality. And there was no clearer example of that, for all of us, than during the Covid shutdowns. That’s when I met actress and singer Adrienne Walker and asked her to come on the podcast. She's appeared on Broadway in The Lion King and Kiss Me, Kate as well as the Dirty Dancing national tour. It’s hard to believe that it was five years ago—in the midst of our industry being turned upside down—that she and I sat down and talked about finding purpose as actors and the determination to keep going. That’s something that remains an issue even after the pandemic. Whether professional projects or personal goals, whatever comes her way, Adrienne handles the ups and downs with perseverance and humor. She shows us that resilience isn’t some grand gesture, it’s the steady, everyday choices that make the difference. -- Watch Now You See Me, Now You Don't from the New Works Virtual Festival in 2020. Follow Adrienne: Website / Instagram / IMDB / 32 Bar Cut Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 33m
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4.3
out of 5
29 Ratings

About

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.

Information

  • Creator
    Patrick Oliver Jones
  • Years Active
    2017 - 2026
  • Episodes
    410
  • Rating
    Explicit
  • Copyright
    ©2026, WINMI Media
  • Show Website
    Why I‘ll Never Make It

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