We asked two of our 2025 Season Directors to share some behind-the-scenes insights about their upcoming productions, their artistic inspirations, and what excites them most about bringing these stories to life. Here’s what they had to say!
Matthew Windham
Q: What show are you directing for FlagShakes, and what excites you most about it?
A: I’m directing Complete Works. I love watching skilled comedians at work, and being able to offer ideas to heighten and hone every comedic beat. I’m looking forward to spending several hours a day in a room filled with laughter. What could be better?!
Q: What’s the most rewarding or exciting part of directing with FlagShakes?
A: FlagShakes is a small but mighty band of talented and committed theatre-makers who I respect a ton. It’s an enormous honor to be part of the team.
Q: When you’re casting, what qualities do you look for in an actor?
A: Inventiveness, quirkiness and adaptability.
Q: Do you have a favorite FlagShakes memory from a past production?
A: I always looked forward to fight-call before every performance of Julius Caesar. There was something really special about getting to laugh and play with all my buddies in the cast, then turn deadly serious for a few moments as we ran through the fights and I got stabbed a bunch, and then check in with each other. You really couldn’t get murdered by a nicer group of people.
Q: What’s a fun fact about you that our actors and audiences might be surprised to learn?
A: I’m a very proud papa to the 3 best cats on this planet.
James Cougar Canfield
Q: What show are you directing for FlagShakes, and what excites you most about it?
A: I’m directing Emma, an adaptation of Jane Austen’s novel by Matthew Windham. Just being in Flagstaff itself is such a magical experience. The forest, the mountains- living in NYC and getting to escape this to this beautiful place for a few weeks to create art is so fantastic. Outside of location, it’s a group of people that I feel so comfortable with- they know how to take care of a team and know how tell a story, and support you in telling that story.
Q: What’s the most rewarding or exciting part of directing with FlagShakes?
A: With both projects I have previously directed for FlagShakes (As You Like It and The Importance of Being Earnest), we took some pretty big artistic swings, and the patrons were like, “let’s go, we’re coming along for this wild ride right there with you!” You can do these classics in new, exciting ways, and the FlagShakes audiences are going to be there for it. I love taking classical stories/scripts and telling them through a modern lens, and I think Emma is so very perfect to be explored like that- and I cannot wait to see what Matthew, the ensemble, and myself can create with this Jane Austen classic.
Q: When you’re casting, what qualities do you look for in an actor?
A: Big, fun choices and truth. Especially in a story like Emma, we need actors who are ready to have fun and fill the shoes of these iconic characters, but no matter how big the choices, the actor is always bringing truth to the table. I’m interested in actors who allow themselves into the text- yes, this is a classic story, but how do YOU as a performer fit into it? How do you bring YOUR truth?
Q: Do you have a favorite FlagShakes memory from a past production?
A: I loved getting to play Sir Toby Belch in Twelfth Night with FlagShakes. Jim Warren, the director of the production, really just let me run wild with how silly and stupid that character could be, and I just don’t often get the chance to be -that- over the top.
Q: What’s a fun fact about you that our actors and audiences might be surprised to learn?
A: Not really as fun fact, but I am currently directing my adaptation of The Secret Garden with Southwest Shakespeare Company. It performs April 4-13th at Taliesin West in Scottsdale, AZ.
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