Interview: Playwright Stephen Sheffer and LEAN-TO at 59e59 Theaters
Stephen Sheffer is a Canadian-born, Brooklyn-based playwright, screenwriter, performer, and teaching artist.
New Light Theater Project and Pendragon Theatre will present the world premiere of Lean-To, written by Canadian playwright Stephen Sheffer, and directed by Jesse Jou. It will be running from September 10 to October 10, 2026 for 32 performances in a limited 5-week engagement at 59E59 Theaters. Previews begin September 10 for the September 13 opening.
Lean-To tells the story of an overprepared hiker and a not-so-prepared couple are forced to share a rustic lean-to shelter in the woods. Bonding over Britney Spears, shared supplies, and the desire to escape city life for a weekend, these strangers experience a rare moment of authentic connection. But as they come together around the warmth of the campfire, a different type of kindling threatens to combust.
Broadwayworld had the pleasure of interviewing Stephen Sheffer about his background and the upcoming show at 59E59 Theaters.
Stephen Sheffer is a Canadian-born, Brooklyn-based playwright, screenwriter, performer, and teaching artist whose work explores the wild worlds inside and all around us. His plays include Lean-To (59E59 Theaters, New Light Theater Project), SOS (upcoming reading at 59E59), Private Property (Out of the Box Theatrics), the award-winning Back To Mine, and the one-acts The Spark (The Barrow Group) and IRMPOV SHOW. For the screen, he writes both independently and with collaborator Meghan Hemingway on projects including Geri Atrick Mayor (Bell Canada), The Innkeepers, and Archipelago. His work has been seen at Ars Nova, Rattlestick Theater, Cherry Lane Theatre, HERE Arts Center, Hartford Stage, and The Flea. As an improviser, Stephen is a founding member of NYC’s Dirty Little Secrets Improv Show, which has been running in the East Village since 2015, and is the co-creator and co-host of the triviatastic “Feelz Right Quiz Night.”
What was your very first theatrical experience?
My mum was an avid theatre-goer and took me to see all sorts of stuff. I grew up in Ottawa, Ontario where there was a tucked-away theatre in a renovated truck garage in Little Italy called the GCTC (Great Canadian Theatre Company). My mum would always take me there to see whatever was on. The show that stands out in my memory as my very first was a one-woman show by Djanet Sears called Afrika Solo. I also remember seeing Cul-de-sac by Daniel MacIvor there. Both these shows made a huge impression on me, and were arguably not necessarily intended for kids. I mean, I also saw Phantom as a child, and that was formative, too, but I was lucky enough to be exposed to more experimental, and less overtly commercial, forms. Plus, I started working professionally when I was 9, in a production of Carmen at the National Arts Centre of Canada, so I guess theatre got me pretty early. Thanks Mum!
Have you had any particular mentors in your career?
The person who comes to mind right away is my playwriting prof at Queen’s University in Kingston, Ontario: John Lazarus. I was in his first-ever class at Queen’s and he put so much effort into supporting us, reading our work and fostering our voices. John made me feel like I had something to say through drama. I recently saw him for a coffee, actually, and wouldn’t ya know — he has a play called Running Wilde going up in Vancouver the exact same time as Lean-To here in NYC. Thanks John!
What piece of advice can you share with aspiring writers?
Say yes to your own ideas. Get it wrong. Hook up to the source of creativity, whatever that means to you, and be a channel for it. And see a million plays.
As a playwright, performer, screenwriter and teaching artist, how does juggling multiple roles in entertainment enhance your career?
Oh, you know, just a multi-faceted boy living in a multi-faceted world. I think we’re all obsessed with that clip from Amy Poehler’s interview with Jonathan Groff when he quotes from Merrily We Roll Along: “Facing facts / Not escaping them / Still with dreams / Just reshaping them.” That feels very apt to how juggling all these roles enhances my career. Because when all is said and done, the play’s the thing.
What would you like audiences to know about Lean-To at 59E59 Theaters?
The play is set in the woods and, living in NYC, we don’t often get to go into the forest too much. Did you know that 400 years ago, Times Square was a red maple swamp teeming with beaver dams? The natural world isn’t a distant memory, it’s underneath and all around us all of the time. I want audiences to come to the show and feel connected to that wild part of themselves and the wild world all around them, too.
Please tell us a little about the cast and creative team that is bringing the show to the Upper East Side stage.
The play is directed by Jesse Jou, who I had never met before working with him. But I saw a production of Our Town that he directed in The Adirondacks at The Pendragon Theatre, and the third act was staged in a cemetery next to the theatre. I bawled, and the whole production was gorgeous. So I’m really excited for him to bring that magic to Lean-To. And the cast is stacked. 59E59’s description of the play calls it “part comedy and part tender drama” and I think that’s true. John Alejandro Jeffords, Larisa Oleynik and Joshua David Robinson all know how to walk that line of comedy and drama so expertly. And I’m particularly excited for when Larisa, as Yvonne, fully pops all the way off.
Can you share with us any of your future plans?
My new play SOS, about a group of coworkers who embark on a team-building trip to the Grand Canyon gone horribly wrong, is being staged as a reading at 59E59 while Lean-To is running. And I’m scribbling away on a new play currently titled A Hundred Year Flood RIGHT NOW. That’s what I was working on right before this interview, actually. More on that another time.
59E59 Theaters is located at 59 East 59th Street (between Park and Madison Avenues) New York, NY 10022. Tickets for Lean-To and upcoming shows are available by visiting Home | www.59e59.org.
You can follow Stephen Sheffer on Instagram https://www.instagram.com/dasenpearce and visit his website at https://www.stephensheffer.com
Photo Credit: Justin Belmondo
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