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

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

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.

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)

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)

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.

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.