As Why I’ll Never Make It approaches its tenth season, this special retrospective looks back at ten conversations that helped shape this podcast in meaningful and profound ways. Since 2017, this has been a place to talk honestly about a career built on uncertainty, rejection, hope, and persistence. And over time, it’s become something far more personal than I ever expected—a place where success is never the most interesting part of the story.
This revisit isn’t some “best of” series or a collection of the biggest names. These episodes feature artists who showed up with honesty and openness, sharing the setbacks, questions, and quiet work it takes to keep going. Across the next several weeks, you’ll hear voices like Anthony Rapp, J. Harrison Ghee, Ann Harada, Lynn Nottage, and others whose stories still resonate, reminding us why these conversations matter and why they’re worth hearing again as we head into season ten.
Transcript
As I get ready to launch the tenth season of Why I’ll Never Make It, I’ve found myself looking back—not in a nostalgic or congratulatory way, but one of gratitude and admiration. I mean since 2017, I’ve talking out loud about an industry that’s built on uncertainty and confidence, rejection and hope, and a sizable helping stubborn persistence. And somewhere along the way, this podcast stopped being just a place to interview artists, and became something much more personal and meaningful.
So for the next several weeks you’re going to hear ten conversations that have impacted me—as an actor and as the host of this podcast, but also as a fellow listener with you. Now, this isn’t gonna be some “best of” series. These aren’t the biggest names or the episodes with the most downloads. This is a very intentional look back at artists who showed up fully, who talked openly about doubt, missteps, identity, grief, resilience, and the quiet work it takes to keep going. You’ll hear from guests like Anthony Rapp, J. Harrison Ghee, Ann Harada, Lynn Nottage, and Misha Osherovich—artists whose careers are very different and varied, yet whose honesty connects in a powerful way.
I’ve had so many wonderful guests and friends come on this podcast, and so picking just ten was difficult and took some time. Some conversations, like the one I had with playwright Cris Eli Blak, were so personal and moving and would be a natural fit on this list. But that conversation has already had a rewind episode a few years back, so I wanted to pick 10 interviews that haven’t been revisted yet. And these in particular are such worthy reminders of why I started this podcast in the first place, and why it still matters—to me, and to so many of you who’ve reached out over the years to say, “I needed to hear that.” And the lessons contained in these conversations are as relevant today as when we first had them.
So as we head into season ten, consider this a pause and a deep breath—a chance to reconnect with the voices and stories that made Why I’ll Never Make It what it is—a space where honesty matters more than optics, and where success is never the most interesting part of the story.
