Stagecraft: Bubba Weiler on “Well, I’ll Let You Go”

Summary

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BroadwayRadio: Stagecraft – Bubba Weiler on “Well, I’ll Let You Go”

Date: August 19, 2025
Host: Jan Simpson
Guest: Bubba Weiler

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Episode Overview

In this episode of Stagecraft, Jan Simpson interviews actor and playwright Bubba Weiler on the occasion of his debut play “Well, I’ll Let You Go,” playing at The Space at Irondale in Brooklyn. The conversation explores the play’s themes of grief and community, Weiler’s transition from actor to playwright, casting a dream ensemble, influences like “Our Town,” and the collaborative process that has shaped this production.

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Key Discussion Points & Insights

1. Introduction to “Well, I’ll Let You Go”

• Theme & Tone:
  The play centers on a middle-aged woman, Maggie, coping with the sudden loss of her husband.
  • Bubba is intentionally vague about plot specifics to preserve the play’s layered, slowly-revealed mystery.
  • Key Themes: Loss, regret, community, and the disillusionment with the American dream.

    “It's a show about loss and regret, and it's about a community and a marriage that is sort of bought into an American dream that has sort of crumbled and isn't serving them.” (C, 02:17)

2. Origin and Personal Connection

• Genesis in COVID-19:
  The idea came to Bubba shortly after the start of the COVID-19 pandemic, reflecting on deaths in his hometown in Illinois and the alienating nature of Zoom memorials.
  • Explores the awkwardness and shortcomings of grief rituals in disconnected times.

    “All the helpful things about a memorial, you know, being with loved ones and connection, were stripped away... the only thing that was left were these sort of strange ceremonies.” (C, 02:54)

3. Writing a Middle-Aged Female Protagonist

• Personal Background:
  Bubba reveals his large, multigenerational family and experiences as the youngest, often surrounded by adults, led him to empathize with, and write from, older perspectives:

  “I was spending all of my time around adults... For this play, I just gravitated towards the lives and emotions and inner workings of some of the older people in my life.” (C, 04:30)

4. The Impact of Casting and Collaboration

• Dream Cast:
  Weiler’s first production boasts a cast he admires, including Quincy Tyler Bernstein and Michael Chernis.

  • No roles were written with specific actors in mind, but casting through Taylor Williams and the reputation of director Jack Sierio attracted elite talent.

    “It's really mind blowing to me. But I did not write this play with any actors in mind... And when Quincy and Michael's name came up, we just got so obsessed with that idea and just prayed and prayed... And they both said yes.” (C, 06:29)

• Praise for Quincy Tyler Bernstein:

  “A lot of that credit should go to Quincy Tyler Bernstein, who gives just an incredible performance and just really, really fills out this woman in ways that my writing sort of never could.” (C, 05:25)

5. Play Structure and the Influence of “Our Town”

• Structure Inspired by Acting:
  The play features a series of two-character scenes, providing each of the eight actors a moment to “shine.”

  • The structure evolved with the introduction of a narrator character.

• Explicit Influence:
  Weiler is deeply inspired by Thornton Wilder’s “Our Town,” particularly the narrator device and sense of community.

  “Our Town is my favorite play in the world. I just find it so touching and... it reaches for these big questions that I think sort of only theater can touch.” (C, 09:25)

  • He seeks to update “Our Town” for today’s America, reflecting contemporary struggles while honoring ordinary decency.

    “At the end of the day, I do think that Americans are good, decent people just trying to get by.” (C, 10:44)

6. Transition from Acting to Writing

• Early Passion for Playwriting:
  Bubba has written plays since age 15, influenced by the new play development culture in Chicago.
  • Only recently has he started showing his plays; previously, acting had taken precedence.
• Collaboration with Jack Sierio:
  Bubba and Jack’s collaboration stretches back to college, with Bubba actually serving as Jack’s playwriting TA.

  “Jack and I went to college together. I was Jack's playwriting TA for his freshman playwriting class.” (C, 12:38)

7. Intimacy of the Production

• Design Ethos:
  Both Bubba and Jack value the authenticity and simplicity reminiscent of Chicago storefront theater—unflashy, actor-driven storytelling, often in unconventional spaces.
  • The “runway” audience setup enhances a sense of community.

    “Jack... wants you to be able to sit across from the people who are watching it and feel like you're all experiencing this together and that you're a part of the story.” (C, 13:24)

8. Acting Background’s Influence on Playwriting

• Bubba credits his acting instinct for his sense of dialogue rhythm and natural drama pacing, as well as his trust in actors’ input during development.

  “When they flag for me that a moment isn't working, I just innately trust them, that they know more inside of it than I do outside.” (C, 14:54)

9. Looking Ahead: Acting & Writing

• Bubba aspires to balance acting and playwriting, following in the footsteps of artists like Tracy Letts and Kiriti Weap.

  “I love acting. I definitely don't want to give it up. And I, and I have very much enjoyed my time, my short time as a playwright... that's the dream.” (C, 16:11)

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Notable Quotes & Memorable Moments

• On grief rituals:
  “The only thing that was left were these sort of strange ceremonies that we do…how desperately people try to be helpful in a time like this and how often it falls short.” (C, 02:54)
• On being actor-focused in writing:
  “I'm a writer that will always be sort of actor first because that's my background.” (C, 14:54)
• On Chicago theater’s influence:
  “Chicago theater takes place in largely storefronts…It's just good, solid storytelling with excellent acting.” (C, 13:24)
• On the play’s American spirit:
  “At the end of the day, I do think that Americans are good, decent people just trying to get by and live their lives.” (C, 10:44)

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Timestamps for Key Segments

• [02:17] – Bubba describes the play’s core themes without giving away the plot.
• [02:54] – Genesis of the play during COVID and development of grief as a central topic.
• [04:30] – Explaining why the protagonist is a middle-aged woman.
• [06:29] – On casting Quincy Tyler Bernstein, Michael Chernis, and more.
• [08:29] – Describing the play’s two-character scene structure.
• [09:25] – Discussing the influence of “Our Town” and its thematic parallels.
• [12:38] – Origins of the writer-director collaboration.
• [13:24] – The value of intimate, actor-driven, community-rooted theater.
• [14:54] – How acting experience shapes Bubba’s playwriting.
• [16:11] – Balancing ambitions for acting and writing.

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Summary

This episode provides a compelling, inside look at how Bubba Weiler crafted “Well, I’ll Let You Go,” weaving his personal and professional experiences into a poignant piece about grief, community, and the evolving American Dream. The conversation explores his creative process, the invaluable role of collaboration and casting, the major influence of “Our Town,” and the seamless blend of acting and writing in his career. Listeners gain not only insight into the play itself but also a greater appreciation for the artistry and thoughtfulness fueling this new voice in American theater.

Transcript

[A]

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[B]

Every musical begins with some writer putting words on a page hello and welcome to Stagecraft, the Broadway radio podcast that talks to playwrights and musical book writers about the shows they've created. My name is Jan Simpson. My guest for this episode is Bubba Wyler, who has made an impressive playwriting debut with his first produced play, well, I'll Let yout Go. As you'll hear in our discussion, he doesn't want to give away too much about the plot before people have the chance to see it, but I think it's okay to say that it centers around a middle aged woman grieving the sudden and unexpected death of her husband. Its run has just been extended at the Space at irondale in the Fort Greene section of Brooklyn through September 12, although its star, Quincy Tyler Bernstein, has a previous commitment that will only allow her to stay through August 29th. Hello, Bubba Weiler, welcome to Stagecraft.

[C]

Hi. Thank you so much for having me.

[B]

As I think, you know, we usually start these conversations with a brief description of what the show is about. Now, I know you're reluctant to give too much away about your show, but could you give some sense of what well, I'll Let yout Go is about?

[C]

Yeah, just, you know, for listeners that haven't seen the show yet, the show does have sort of a sort of slow burning mystery to it and it sort of reveals itself in layers. So to say too much about the plot, I think sort of spoils your experience from the jump, but it's easier to talk about the themes. It's a show about loss and regret, and it's about a community and a marriage that is sort of bought into an American dream that has sort of crumbled and isn't serving them.

[B]

Where did you get the idea for this play? What's the genesis of it?

[C]

So I started writing this play like a week into Covid, and the truth is a lot of community Members from my home in Illinois were dying and we were having these sort of strange zoom memorials for them. And it sort of highlighted how strange everything is that we do when a person dies. And was made even more strange by the distance and the disconnection. Sort of all the helpful things about a memorial, you know, being with loved ones and connection, were stripped away and the only thing that was left were these sort of strange ceremonies that we do. So I started to write a play about. About that, about the different ways that everyone grieves and how desperately people try to be helpful in a time like this and how often it falls short just because nobody sort of knows how to act and nobody knows what they need in those moments. It's just a process that you have to let unfold.

[B]

You are a relatively young guy.

[C]

Yeah, that's generous.

[B]

And the main character in your play is a middle aged woman. And so again, I'm going to ask, how did you choose to center your play around this woman? Maggie?

[C]

I am the youngest of six children and beyond that, I am one of the youngest cousins in a big family of probably 30 cousins. This is all on one side, you know, seven aunts and uncles and just as many on the other. So my life was sort of filled with people that were older than I. And I was also a child actor growing up, so I was spending all of my time around adults. So, you know, I do have plays that concern characters more my age and some younger. But for this play, I just, I just gravitated towards the lives and emotions and inner workings of some of the older people in my life.

[B]

Well, it's impressive that you were able to get into the skin, the soul, the spirit of this woman who is, I guess, in her 50s or so.

[C]

Thank you so much. I mean, I think a lot of that credit should go to Quincy Tyler Bernstein, who gives just an incredible performance and just really, really fills out this woman in ways that my writing sort of never could. You really need a great actor to make it three dimensional and to take it to that next place. And Quincy does that so beautifully.

[B]

Well, you, you've jumped ahead, so I'm going to jump ahead with you because I wanted to talk to you about the casting of your play. Your play is just stacked with some of actors working in this city. And so how did the this come about? Were these people that you had worked with or that your director Jack Syrio had worked with before or did you write specifically for these actors? And I'm thinking in particularly of Quincy Tyler Bernstein and Michael Chernis. Who serves as sort of the narrator of your play.

[C]

Yeah. The cast is in embarrassment, riches. It's all of my favorite New York actors. I feel so grateful to be a playwright who's having his first ever production with a cast like this. It really. It's really mind blowing to me. But I did not write this play with. With any actors in mind. I mean, I. I am extremely familiar with. With Quincy's work and Michael's work and have been such huge fans of them for so long, but I didn't imagine that they would be available to me in my first production or ever. But we worked with an amazing casting director, Taylor Williams, who presented us with some actors who she thought would connect with the script. And when Quincy and Michael's name came up, we got just so obsessed with that idea and just prayed and prayed and prayed that they would say yes and it would work out. And. And they both said yes. And so did all the other actors who I so greatly admire. And the truth is, you know, Jack Sierio, our director, has been doing just incredible work for these last, you know, three, four, five years. And he is somebody that actors really want to work with. So some of the cast are people that he has worked with in past. And Will Dagger was in his production of Uncle Vanya. I know he's worked with Emily on some workshops.

[B]

This is Emily.

[C]

Yeah, yeah. And Emily Workman. And so, you know, a lot of these actors are attracted to the project because Jack has such a great reputation.

[B]

Well, I think they're also attracted to the play itself. You mainly structured the play as a series of two character scenes. I don't think this spoils it too much.

[C]

No, not at all.

[B]

Where each of the eight actors gets a chance to shine. Was that always your structure or did it change as you developed the play?

[C]

So that is the initial sort of seed of the idea. I'm an actor myself, and I started this play with structure, and then it filled it in with content. And, you know, my first idea was I wanted to write a play that felt like it was a bullpen of New York's best actors, and each actor gets one swing, gets one at bat. And the structure changed slightly from that once I started thinking about the narrator character. And so that. That was slightly later in the game that I. That I started to experiment with that.

[B]

We referred to the narrator character. And I don't think one can refer to a narrator character without there being echoes of our town.

[C]

Yeah, yeah.

[B]

And I wondered how conscious were you of that connection as you were Developing the play extremely.

[C]

That was, that is one of the main goals of this production. In this play, Our Town is my favorite play in the world. I just find it so touching and, you know, it reaches for these, these big questions that I think sort of only theater can touch. For me, at least, that's the medium I go to, to talk about these sort of big lifey questions. And when I was young, I saw David Cromer's production of Our Town, first in Chicago and then in New York. I was a teenager and it really sort of changed my life. And I had been thinking, you know, when I was writing this, it was, it was during COVID and during Trump's first presidency and there was a lot of anger and turmoil in this country. And, you know, I started to think about Grover's Corners a little bit and think about the, the beauty of that town and that time and sort of the simplicity of, of good people trying to get by. And that's sort of what I'm trying to convey with this piece, is that those people still exist. We're just existing in the, in a context that is uglier. And at the end of the day, I do think that Americans are good, decent people just trying to get by and live their lives. So the idea of this play was sort of an attempt to give our town a bit of an update. But I didn't think that our town wanted to, wanted a one to one update. I didn't want to say like, this is Grover's Corners 2025. So I, you know, I said it within my context. I took it to, towards the people that I know and grew up with. And that's sort of where I jumped off from.

[B]

Now I think some theater goers will know you as an actor and a very good actor. I've seen you. So why write a play?

[C]

I have been writing plays since I was about 15 years old. That's always been a passion of mine. I grew up a child actor in Chicago. And one of the gifts of that was I got a front row seat to some excellent new play development and I just loved it. And I paid attention and I watched these great Chicago artists experiment and make great, you know, messy, beautiful, difficult plays in storefronts for an audience of 30 people, sometimes or, you know, sometimes 500. But, but just the discipline of that and the joy of that was something that I was always attracted to, and I learned a lot from it. You know, I've watched great playwrights and great directors make plays better. And so new play development has always Been what I'm interested in. It's what I want to do as an actor. It's obviously what I'll hopefully will continue to do as a playwright. But. Yeah, since I was a kid, Since I was 15, I've been sort of secretly writing plays in my room. And then I did study it in college, but the acting thing just sort of happened for me first. And I never showed anybody my plays until last year. I started sharing them with Jack, and he thought we should put this one up.

[B]

Had you worked with him before, or how did the two of you.

[C]

Jack and I went to college together. I was Jack's playwriting TA for his freshman playwriting class.

[B]

So a long time, then. Relationship. Jack seems to have specialized over the last couple of years in these intimate performances. This production is also an intimate production. It's done in a small space with a relatively small audience. Was that something that was in your head or that once you knew that Jack was going to do, it came about.

[C]

It's interesting because it's something that attracted me to Jack's work in the first place. I love Jack's work partly because it reminds me of the work that I was seeing and loving in Chicago. You know, Chicago theater takes place in largely storefronts. And so there's sort of strange, unexpected spaces, and they don't have anything extra. Right. It's just good, solid storytelling with excellent acting. And that's what I think Jack is so good at. He really pares things down to the essentials. It's the acting, it's the storytelling, and it's beautiful design, but it's design that isn't flashy. And so that's what attracted me about his work. But when I wrote this and handed it to Jack, I wasn't quite picturing it the way that we have presented it. I had sort of pictured it in proscenium, our shows in a Runway. And one of the reasons Jack did that is he wants it to feel more like a community event. You know, he wants you to be able to sit across from the people who are watching it and feel like you're all experiencing this together and that you're a part of the story. He didn't want people too far away from it, which I think is an excellent impulse. So kind of all the things that I love about his work, he then, you know, put into my work. And it's very moving and exciting to me.

[B]

Has being an actor affected the way you write?

[C]

Absolutely, yeah. I think being an actor, you innately have a good sense of rhythm. Right. And there's just, there's instinct on where a scene should go and when and what can realistically get a character to an emotional point that you need them to story wise. Right. And then I think the other thing that it's done for me is given me just so much trust in actors. I mean, especially obviously with this excellent cast. When they flag for me that a moment isn't working, I just innately trust them, that they know more inside of it than. Than I do outside. Because I've had the experience of being, of being inside something and seeing it not necessarily better, but differently. And so, yeah, I'm a writer that will always be sort of actor first because that's my background.

[B]

So looking ahead, will you sort of follow the Harold Pinter, Tracy Letts approach where you do some acting, do some playwriting?

[C]

I hope so. I love acting. I definitely don't want to give it up. And I, and I have very much enjoyed my time, my short time as a playwright. Kiriti Weap is a hero of mine and he is, he is sort of the model. So, yeah, that's, that's the dream.

[B]

Well, right now we're very glad to have this production. It's a, it's a sensational way to start.

[C]

Thank you. Thank you.

[B]

And thank you for taking the time to talk with us.

[C]

I had such a good time. It was a delight.

[B]

And thank you for listening. I hope you'll come back next time. And if you have any comments, questions or suggestions, please send them to [e-mail].