How do LLMs handle dialogue and subtext?

When playwright Matthew Gasda credited ChatGPT and Claude in the program for his play Doomers, it sparked a debate about whether machines belong in the creative process. The play wasn’t written by AI. It used AI as a dramaturg, a kind of philosophical collaborator, and that simple credit forced audiences to confront what it means to create alongside a machine. In this episode, Dart talks to Matt and Isobel about AI as dramaturg, the creative tension between human and machine, and how the source of a work might matter as much as the work itself.

Matthew Gasda is known for reinventing New York theater with intimate, independent productions that challenge how art is made and who it’s for. Microsoft language scientist and producer Isobel McCrum joined him after seeing Doomers, bringing her fascination with the intersection of language, technology, and creativity.

In this episode, Dart, Matt and Isobel discuss:
- When an audience debate exposed our unease with AI in art
- The origin of Doomers and its link to Sam Altman’s firing
- AI as a dramaturg, not a co-author
- How Isobel trained a model on Matt’s plays to study imitation
- What happens when a playwright prompts a machine to think
- Why AI-generated writing often feels like parody
- How Borges’ Pierre Menard changes how we see authorship
- Can AI art still carry human depth?
- What does it mean for art to be both human and synthetic?
- And other topics…

Matthew Gasda is a playwright, novelist, and founder of the Brooklyn Center for Theater Research. He’s known for reinventing New York theater with intimate, independent productions that exist outside traditional institutions. His plays, including Dimes Square, The Sleepers, and Doomers, explore modern culture through realism, philosophy, and personal reflection. With Doomers, he captured the human drama behind Sam Altman’s near firing from OpenAI, using theater to question creativity, technology, and what it means to be human.

Isobel McCrum is a language scientist and content designer at Microsoft, where she works on the language experience for AI tools like Copilot in Word. With a background in linguistics and storytelling, she focuses on making AI systems more precise, inclusive, and human-centered. Isobel also collaborates on creative projects that investigate the intersection of art, language, and machine intelligence, including Doomers, which she produced for its London release.

Resources Mentioned:
Doomers: https://www.doomerslondon.com/
Brooklyn Center for Theater Research: https://brooklyncenterfortheatreresearch.com/

Connect with Matt and Isobel:
Matthew’s Substack: https://substack.com/@matthewgasda
Isobel’s LinkedIn: https://www.linkedin.com/in/isobel-mccrum/

Work with Dart:
Dart is the CEO and co-founder of the work design firm 11fold. Build work that makes employees feel alive, connected to their work, and focused on what’s most important to the business. Book a call at 11fold.com.