Why I‘ll Never Make It

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

After seeing Misha Osherovich in an Off-Broadway production of A Clockwork Orange, I began following Misha’s work and perspective online. A couple of years later, a deeply personal post about body image and eating disorder struggles stopped me in my tracks—speaking to something many of us face in this industry but don’t always say out loud. That moment led me to reach out, and eventually to this conversation. Recorded in 2019, this episode explores the pressures performers face when it comes to appearance, self-worth, and the constant scrutiny of both the industry and ourselves. What follows is one of the most candid and compassionate conversations I’ve had on the podcast. Misha Osherovich opens up about mental health, personal fears, and the work of separating identity from external validation, all with a level of honesty that is both unflinching and deeply empathetic. It’s a reminder that the most meaningful work often begins with telling the truth about lived experiences—and having the courage to share that truth. (Note: at the time of this interview in 2019, Misha Osherovich was using he/him pronouns but now identifies as non-binary, using they/she.) Learn more about your ad choices. Visit megaphone.fm/adchoices

Growing up, it was my mother who sang in the church choir about the time I was joining the children’s choir, and my aunt spent her young adult years performing as a jazz singer. But I’m actually the first in my family to pursue a full-time career in theater. That gave me a certain freedom to find my own way through the industry, but it also meant navigating a path no one in my family had taken before. For artists like Sharon Catherine Brown, though, there’s a different experience entirely—one shaped by a legacy of performers who came before. While she has worked in television and film, theater has always been her first love, with numerous Broadway and national tour credits, including her current run on the road with The Notebook national tour. Sharon joined the podcast back in 2023 to talk about following in the footsteps of her talented family and honoring the profound influence they’ve had on her life and career. I also had the joy of working with her in the summer of 2022 at Goodspeed Musicals in Connecticut on a new musical adaptation of Anne of Green Gables. As Anne herself might say, Sharon quickly became a kindred spirit in my life—and as you’ll hear, we truly enjoy each other’s company. In fact, our conversation lasted more than three and a half hours. When it was first released, I split it into two episodes, with the Final Five Questions available only to subscribers. For this Look Back episode, I’m bringing the entire conversation together in one place—lightly edited, but still full of the heart, wisdom, and passion Sharone shares so generously. Learn more about Sharon's connection to her father, Johnny Brown⁠, and his career. Follow Sharon: Instagram / IMDb / IBDB Learn more about your ad choices. Visit megaphone.fm/adchoices

Since making my Broadway debut in Beetlejuice last year, I’ve spent a lot of time thinking about what it actually means to “make it” in this business. It took me twenty years from my first Broadway audition to finally getting that credit, with plenty of near misses along the way. But imagine being just ten years old and moving to New York City with your family for your Broadway debut…only to have the show close during previews. That’s exactly what happened to Anthony Rapp. Recorded in 2022 as the theater industry was finding its footing again after the COVID shutdown, our conversation goes far beyond the role many people know him for—Mark in Rent. Anthony reflects on that almost Broadway debut, the reality of film producers who didn’t want to cast him, and how he navigated the loss of two people closest to him. You’ll also hear a bonus segment about his time playing the title role in You’re a Good Man, Charlie Brown. Correction: In the episode introduction, I mistakenly referred to Anthony Rapp as playing Roger in Rent. Anthony actually originated the role of Mark Cohen on Broadway. Also, with it being mentioned during the episode, Anthony’s answers to the Final Five Questions can also be found here. Follow Anthony: IMDb / IBDB / Instagram Learn more about your ad choices. Visit megaphone.fm/adchoices

After working with Lisa Howard in 2022 on a production of 42nd Street at Goodspeed in Connecticut, she sat down with me the following year to chat about her career and of course reminisce about our time together doing that show. She is so spirited and cheerful, and that’s reason enough to love this conversation. But what made it so memorable is how she pulls the curtain way back and reveals the trials and tribulations of putting a new show together, some more successfully than others. Because for nearly twenty years, Lisa Howard has made a career out of originating roles on Broadway from The 25th Annual Putnam County Spelling Bee to 9 to 5 and Escape to Margaritaville. She shares what it’s like to survive a rehearsal process that feels impossible, to be part of a show the cast loves even when the critics don’t, and to help shape a piece of theatre while it’s still trying to figure out what it is. And then we discuss a topic everyone asks her about, but this time in a way that lets her define the story for herself. Follow Lisa: Website / IBDB / Instagram Learn more about your ad choices. Visit megaphone.fm/adchoices

I think most of us actors hope to be in a hit Broadway show or a popular film or highly rated TV show. But for those actors lucky enough to be in one, it can sometimes be all you’re known for and all your other work either goes unnoticed or forgotten. For example, you’ll hear from Anthony Rapp in a few weeks, that even with all he’s done onscreen and onstage, for most of us he will forever be Mark in the Broadway musical Rent. Now I imagine, that must be immensely rewarding to be in a show like that that made such an impact, but some days I’m sure it can be a little frustrating to feel like the world only sees one piece of what you do. That certainly applies to a guest I talked to back in 2021, Geoffrey Owens. I was so excited when he agreed to come on the podcast. I mean, I grew up watching him and the Huxtable family every Thursday night on The Cosby Show. And yes, in this episode we address the shocking downfall of the man once called “America’s Dad” and the toxic figure that Bill Cosby has become. But it was only after doing research for our interview that I discovered all the work he’s done on Broadway and in Hollywood. But then there was the photo of him working at Trader Joe’s that went viral in 2018, which made people see him (and actors in general) in a new light. Geoffrey was an absolute joy to talk to as he shared openly about judgment, perception, and how he’s maintained integrity and focus in a world that’s quick to reduce people to headlines. He shows us that patience and perspective matter more than recognition, and that steady effort always counts. --- Links and References: ⁠Huxtable family watches "I Have a Dream"⁠ • ⁠Carsey/Werner Production⁠ • ⁠Alvin Poussaint Interview⁠ • ⁠Claire sets Elvin straight⁠ Follow Geoffrey: Website / Instagram / IMDB Learn more about your ad choices. Visit megaphone.fm/adchoices

As Why I’ll Never Make It approaches its tenth season, this special retrospective looks back at ten conversations that helped shape the podcast and transformed a simple interview into a meaningful message for us all. This episode features John McGinty, a deaf actor who lost his hearing at a young age and initially headed toward a career in finance, but theater kept calling him back. In this conversation, he shares the realities of auditioning and performing in an industry so dependent on sound and timing, and what it means to pursue this work on his own terms rather than stepping away from it. Recorded in 2018, this episode was also the first video interview ever produced for the podcast, with an ASL interpreter present to ensure the conversation could be fully seen and heard. John talks about making his Broadway debut in the revival of Children of a Lesser God, being the first deaf actor to play Quasimodo in The Hunchback of Notre Dame at Sacramento Music Circus, and continuing to push for greater access and representation in the arts. It’s an honest look at a career shaped not by limitation, but by commitment—and by the belief that this industry can expand when artists insist on being included. Learn more about your ad choices. Visit megaphone.fm/adchoices

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

This past fall 2025 I got to see two of my favorite leading ladies on stage. The first was Christine Sherrill, who was making her Broadway debut in Mamma Mia. She and I had first worked together in the out-of-town tryout for First Wives Club back in 2015 that ran for about a month and a half in Chicago. But due to various factors that show never ended up coming to New York. Nonetheless, Christine was so great in that show. And she brought that same energy and vocal power to the role of Donna in Mamma Mia as well. The second leading lady I got to see was also someone I had worked with before in 42nd Street at Goodspeed in Connecticut. Now, she wasn’t making her Broadway debut, but she was playing a character for the first time: Roxie Hart in the long-running musical Chicago. She has about another month in this role, and so to celebrate her fantastic performance in the show I thought I would replay my conversation from 2022 with this dynamic leading lady...Kate Baldwin --- 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

Step inside the dressing room with Beetlejuice's Justin Collette for a behind-the-scenes conversation that’s equal parts bone broth and backstage banter. From the rock riffs of School of Rock to the undead hilarity of Beetlejuice, Justin shares his wild ride from Canadian improv star and punk band frontman to taking center stage on Broadway. We discuss his his technique of “farting with vocal cords” as well as punk bands and improv nights. It's a season finale with backstage stories, audition adventures (including a fire alarm mishap), and heartfelt reflections on leadership, creativity, and finding joy in the moment. --- 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

Being an actor requires a constant balancing act between showing up creatively and understanding how the industry actually functions. And Jen Rudolph has spent years operating at the intersection of casting, coaching, and strategy. She shows actors how to become clearer, more intentional collaborators in the room and more viable professionals outside of it. Together we talk about her years as a casting director and the creation of The Actor’s Green Room, where she worked closely with actors in person. This eventually morphed into the online space and the leap to fully digital training with the creation of the 2% Signature System. Jen also gives her honest and sometimes controversial assessment of education, access, and the cost of becoming a more bookable professional. Jen’s insights show us why some actors keep getting called in, keep getting trusted, and keep getting hired. And as a special treat, you get my full conversation with Jen in one single episode, something normally reserved for subscribers, that include auditions stories and the Final Five questions. --- 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

Chicago is now celebrating 29 years on Broadway, with multiple national and international companies as well. And for more than two decades David Bushman has been a part of various Chicago productions around the world. But what makes David’s story remarkable isn’t just his longevity with the show—it’s the path that got him there. We talk about his early days in community theater, his unexpected move from a 17-year ballet career into musical theater, and the fact that he booked his first Broadway contract at the age of 50. He shows that “late bloomers” aren’t late at all—they’re just following a different rhythm. --- 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

The previous episode with Trisha Paytas covered so much ground, from her recent Broadway debut in Beetlejuice to her rise as a YouTube star. But one of the best parts of every conversation is when we get to discuss the Final Five Questions. It’s where we hear about personal lessons, hopes for the industry, and those moments that truly define an artist’s career. --- 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

Trisha Paytas joins the podcast to talk about her unexpected and much-talked-about Broadway debut in Beetlejuice. She shares what drew her to the show, how the opportunity came about, and what it’s been like stepping into a completely new kind of spotlight. We also get into her family background and the early days of her online career, how she first gained attention, and the twists and turns of twenty years on YouTube. Trisha speaks openly about the fandom she’s built, the tougher moments she’s faced, and the mental health journey and personal growth that have shaped who she is today. It’s an honest, surprising conversation about reinvention, vulnerability, and the ways we keep learning from both the chaos and the successes along the way. Special thanks to Jimmy Whetzel and Hannah McKinley for their production and editing efforts in putting this episode together. --- 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

In this brief update, I open up about the last several weeks—Broadway opening week, getting sick, and a recent injury—and how all of it pulled me away from releasing new episodes. I share what’s been going on, why the silence stretched longer than I wanted, and how grateful I am for the patience and support of this community as I get things back on track. Learn more about your ad choices. Visit megaphone.fm/adchoices

In the previous episode, Abbie Goldberg and Mason McDowell dove into their new musical 504 as well as the obstacles they’ve faced trying to produce their own works, and it was such an insightful conversation. But there’s still so much more to explore! That’s why I’m thrilled to have Abbie and Mason back here with me for the Final Five Questions—where we get a little more personal by uncovering lessons learned, hopes for the industry, and a deeper look at what drives them as artists. --- 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

Writers Abbie Goldberg and Mason McDowell are the creative team behind 504: The Musical — a new show inspired by the real-life 1977 sit-in that ignited the disability rights movement. What started as a 25-day protest in San Francisco became a landmark moment in history, paving the way for the Americans with Disabilities Act. Abbie and Mason share what drew them to musicalize this event and how they balance storytelling and activism in telling such an important story. We also talk about the ongoing challenges of accessibility within theater itself — from a festival that couldn’t accommodate their actors to the irony of competing for a grant against their own mentor. Through it all, their journey reflects the very message of their show: that change takes persistence, collaboration, and a little bit of creative rebellion. --- 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