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Derek Masterson: Playwright & Screenwriter

  • Writer: Debbie Brenner Shepardson
    Debbie Brenner Shepardson
  • Oct 27, 2025
  • 2 min read

Douglas Frazier

Derek Masterson has been shaping stories across theatre and film for years, with award-winning plays that filled Dublin houses and a documentary that found its way to festivals in Chicago, London, and Fastnet. He writes for Clap ‘n Load Studios and Creative Others, and most of his real impact happens early, in the part of the process people don’t see. He’s looking for the turn where the script finally clicks. Sometimes it’s an actor’s read that gives it away. Sometimes it’s just tightening the stray parts until the story holds. We talked about how those early calls end up steering everything that follows.



When you start a script, what’s the quiet decision that locks the emotional spine before you write a line of dialogue?


Before I commit to a first draft, I usually jot notes to understand the core emotional needs driving the story. Once I know what each character wants, it shapes the direction. Dialogue comes pretty easily once that part is clear.


In rehearsal rooms, what small shift in an actor’s read tells you the play’s center just moved?


When an actor connects to some part of their character, you can feel the honesty. It might be a small gesture or a shift in cadence, but it’s clear they’ve moved closer to the truth of the scene, and that’s what we’re after.


You work across theatre, film, and copy. What hidden craft stays constant no matter the medium?


Clarity. No matter the medium, I try to make sure the material is accessible and the audience understands where we are, what’s happening, and why they’re being told it. Keeping the intention clear — what matters and what doesn’t — is incredibly important. Otherwise you risk losing them.


Collaboration shows up a lot in your posts. What’s the first invisible signal that a partnership will actually work?


When a collaborator builds on an idea with me instead of shutting it down immediately, or when the conversation feels like we’re problem-solving rather than negotiating, I know the partnership has potential. Not every collaboration works. Ego or competitiveness can get in the way, and you do need a little of both, but you still have to be aiming at a common goal rather than trying to be top dog.


In your legal work, writing, and production roles, what unnoticed constraint shapes your storytelling more than any theme or genre?


Whether I’m writing legal documents, shaping a scene, or producing something, I’m always thinking about how people absorb information. With the influence of social media, it's becoming more and more challenging to hold an audience’s attention, and that quiet constraint can decide whether you edit a scene or shorten a paragraph.



When Derek talks about the work, he keeps coming back to how people take things in and where a scene actually holds. He pays attention to the shifts most people miss, the parts that decide whether the story stays clear or drifts. It’s quiet work, but it’s the piece the audience feels even if they never notice it.


Learn more about Derek at:



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© 2025 Debbie Brenner Shepardson

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