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‘Oh, Mary!’ director Sam Pinkleton on the serious power of laughter: ‘The best comedy is grounded in absolute truth’

“There's so few things that we can agree on as a species. Puppies and ice cream are really the only two things that come to mind, but laughing with a group of people feels really good,” says Sam Pinkleton. “It's just not to be underestimated.”

The director is making countless people feel good, courtesy of the hit new play Oh, Mary! After a sold-out run at the off-Broadway Lucille Lortel Theater, the show transferred to Broadway where it has extended multiple times and smashed box-office records at the Lyceum Theater. Pinkleton sat down with Gold Derby to discuss creating comedy with writer and star Cole Escola, and why he credits his directing career to the late Linda Lavin.

Gold Derby: I loved Oh, Mary! Off-Broadway, but I never expected it to transfer to Broadway because it felt so distinctly downtown. What was your reaction to the show's move to the main stem?

Sam Pinkleton: There was quite a lot of caution and questions. I asked many of the same questions that you were probably asking. And what it took was me and the team, including Cole, walking into the completely empty Lyceum Theatre from backstage. So we came onto the stage and looked out into that beautiful house, which looks like an actual wedding cake. That theater is so beautiful and so hilarious because it looks like the theater from The Muppet Show, or if a child drew a picture of a fancy theater. And so immediately I was like, 'Oh, the theater feels like the play!' It's grand and totally over the top and weirdly intimate. I stood on stage and felt like I could have a conversation with somebody in the top balcony. There was something really comforting about the theater. I understood the show there. I mean, I wouldn't call the style of the play exactly subtle. The show was playing to the back row of a balcony at the Lortel. It just didn't have that physical balcony to play to. So there was something about the Lyceum that felt very friendly and inevitable.

What was the biggest shift for you when you prepped the play for Broadway?

I think common logic might suggest it gets bigger and it gets broader and it gets sillier, but actually it felt like an invitation to go deeper and to take it more seriously. Part of what I love about the play and what I think works about it is how seriously it takes itself. There's plenty to be said about how silly it all is, but it is grounded in this really super high stakes story. So we went back into rehearsal and the word we kept using was “deepening.” Let's make the stakes higher, let's make them feel more. I mean, it really felt juicier. It didn't feel like, now we get to wink bigger for the balcony. I mean, that's kind of my worst nightmare actually. It felt like Cole and Conrad [Ricamora] were doing Who's Afraid of Virginia Woolf? when we were rehearsing for Broadway, and that was really fun. It really felt like we had an opportunity for the play to build muscle.

Photo by Amy Sussman/Getty Images

One aspect that has grown for Broadway is the sheer amount, and type, of people who can see it. What is it like experiencing the diversification and expansion of the audience?

It's totally wild. It was not what I expected. There was a very clear moment early on in the Broadway run where I was standing in the back of the theater and I looked at the orchestra and I thought, oh, most of these people are on a New York trip. These are not gay people from Williamsburg. And they were howling! I believe that the play is very warm and very loving and meets people where they are, and people like to laugh. And I've had conservative older people who come up to me with tears running down their faces. … I think asking people to have a nice time is a really big ask that you have to take quite seriously if you want to do it well. I think we've tried really hard to do that. And seeing families from Illinois have as much fun at the Lyceum as tipsy gays from Harlem, is heaven. It's total heaven. Especially because the play is still itself.

One scene that has really stayed with me is Mary's audition sequence. It's just Cole alone on the lip of the stage being hilarious. What is the challenge for you in directing a scene where there is just a sole actor on stage?

That scene really changed when we moved to Broadway because the story of that moment is that Mary has a big audition at a big theater, and it's a big audition on stage. So when we got to the Lyceum, we actually had a room that made her feel small. I think it's so funny to see her little body in that giant skirt come through those curtains. But there is a scene partner, which is the big empty room, and the one person way up in the top of the balcony that she's talking to that she thinks is the director that she's auditioning for. The scale of the room at the Lyceum just made that so fun and so specific. I think it's a really heartbreaking moment in the play because you see how much she wants this, you see how much she wants to get this job and thinks she's going to get this job. And then you see her lose confidence and you see her humiliated. I mean obviously there's crazy screaming laughter in that sequence because she does a lot of totally insane shit, and there's jokes about balls in it, but I also love when the entire audience sighs for her. I would say that that scene was the scene that I learned the most about in previews on Broadway because it is this very delicate dance between her and this person in the top balcony.

It's not every day that you direct an actor who is also the writer of the play. Did that change the way you would normally work with an actor?

I mean, only in good ways. I would say Cole is a real capital-C collaborator, and from our first conversation about this play, it really felt like we were just really in step with each other. We were absolutely making this thing together and we were making the same thing. There definitely have been many moments when I would be like, hey, I need to talk to Actress Cole for a second, or I need to talk to Playwright Cole for a second. And I would make those distinctions. But especially when we got to Broadway or got into performances, Actor Cole was very busy, and so it required quite a lot of trust from Cole to me, to make decisions with the team that they couldn't see. I could write a book about how much I love collaborating with Cole, but it was a really special thing to feel trusted.

The opening night party was held at the Eagle. I love the image of all these prestigious Broadway actors at a leather bar. What image from that night is most seared into your head?

I mean, the rumors that I always hear are “Patti LuPone and Anna Wintour at the Eagle,” neither of which I saw firsthand. But it was the middle of the summer of 2024, and there was a moment where I was like, I am dancing to Charlie XCX surrounded by Broadway producers and my mother at a leather bar. Which is a future that I can believe in. It's a future that I want to believe in more than how I felt at other opening nights, I would say.

Your first Broadway credit was assistant directing The Lyons, starring Linda Lavin, who sadly passed away recently. Would you mind sharing a favorite memory of her?

Oh my gosh. I mean, Linda Lavin is a massive, formative part of why I have continued to love the theater and frankly, why I love being a director. Linda took me so seriously. Linda was one of the first actors of that stature that made me feel like maybe I could be a director. And I just learned by watching her tech that show how mathematical great comedy can be. And also, this is such a cliche but it's true, how the best comedy is grounded in absolute truth. And Linda Lavin could not tell a lie, and she was also poop-your-pants funny and so exacting. I was very lucky, like 12 years later to get to work with her as a director in what was ultimately her last play on stage [You Will Get Sick at Roundabout Theater Company]. And at the time she was, I think 85 or 86, and I went out on a limb and I was like, “Hey, Linda, would you read this weird new play?” And she said yes almost immediately. She took it so seriously and she was adventurous and fearless and so funny and so heartbreaking and memorized four page monologues and did our crazy circle-warmup to Rihanna every day with us. She's the definition of “show people” to me. I don't totally know that I would have stayed a director, were it not for her really being like, oh yeah, you can do this. She taught me the important stuff, how it matters to go to the bar with your company after previews and no matter how it went, have a drink and look people in the eye and say: we're so lucky that we get to do this. That was all Linda.

This interview has been edited for length and clarity.

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