TDF Stages

Sam Pinkleton on why he's following up Oh, Mary! with a pair of super-queer solo comedies

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Long before Sam Pinkleton's triumph at this year's Tony Awards, where he earned the Best Direction of a Play trophy for Cole Escola's smash comedy Oh, Mary!, the gregarious theatrical visionary cut his teeth downtown. Pinkleton began his career as a choreographer, working on shows like Mr. Burns: A Post-Electric Play and Buyer & Cellar before breaking out with Natasha, Pierre & The Great Comet of 1812, which earned him a Tony nomination following the musical's Broadway transfer. Post-pandemic, he started building up his directing résumé, helming genre-defying Off-Broadway projects such as the surreal You Will Get Sick at Roundabout Theatre Company and the gleefully ahistoric Oh, Mary! at the Lucille Lortel, a runaway hit about an unhinged Mary Todd Lincoln that has become the toast of uptown.

While on Broadway Oh, Mary! continues to attract exuberant audiences and actors—the romp just welcomed a brand-new cast headlined by Jinkx Monsoon, Kumail Nanjiani and Michael Urie—Pinkleton has opted to return to his downtown roots this summer with a pair of offbeat, super-queer solo shows from two very different writer-performers: Josh Sharp's ta-da! at Greenwich House Theater through September 11, and Morgan Bassichis' Can I Be Frank? at Soho Playhouse through September 13.

TDF Stages spoke with Pinkleton about navigating the Tony Awards madness, finding himself as a director and why he believes "there's death underneath everything joyous."

Joey Sims: Oh, Mary! transferred to Broadway just over a year ago for a limited run. Now it has two Tony Awards, including one for your work, and has extended into 2026.

Sam Pinkleton: Obviously, it is a total dream come true. And it means even more to be acknowledged for Oh, Mary! because I so deeply believe in how the show was made. I always imagined that if I ever won a Tony, it would be for, like, Hot Wheels: The Musical. I hope this signals to other artists to spend time on the weird stuff you love.

Since I am getting recognized for doing what I love, I've also taken that as a call to action to get really rigorous about the choices I'm making. The two shows I'm working on this summer, ta-da! and Can I Be Frank?, are really awesome examples of that.

Sims: Has it been a relief to follow up the Tony Awards madness with two small gay shows that mark a return to your downtown stomping ground?

Pinkleton: Relief is the understatement of the century. I came up downtown. It is where I am happy and comfortable. Both of these shows are so fun to work on, and the artists at the center of them, Josh Sharp and Morgan Bassichis, are brilliant comic weirdos. It's been so nice to be in a room solving a problem with just like seven people. Because there is a way that Broadway can become about many other things other than directing.

Sims: Right, the demands of Oh, Mary! must be very different now that the show has settled in for a long run. A little closer to management than directing, maybe.

Pinkleton: It is strange and humbling. I've never been in this position before. Oh, Mary! was made in a small room, and everybody got their hands really dirty. And it is in my nature to want to stay really close to a thing. I've had to learn, over the life of it, that's not how that works. So, it has been an exercise in surrender and trust. It's like we're sending our girl off to college.

I'm sure everyone is so tired of hearing the Oh, Mary! people talk about how "surprised" they are. But when I go to see the show now, I look at the audience and I'm like: These people are on vacation. They are tourists… having a wonderful time, seemingly! And that is crazy.

Sims: How do you work with the new Marys and provide room for performers like Betty Gilpin, Tituss Burgess and Jinkx Monsoon to find their own take while still staying true to playwright Cole Escola's text?

Pinkleton: It's at its best when it's a real exchange. But it's not a free-for-all—actually, the secret of Oh, Mary! is that it's quite meticulous. You gotta take her seriously. She's gotta want it, and we have to root for her. So everybody needs to get on board with that. Cole wrote a great part for an actor, and I want to continue testing the limits of how far we can go with that part. Because I think it can hold a lot.

Sims: You initially came up in New York as a choreographer. When did you start to feel like the industry was taking you seriously as a director?

Pinkleton: I really hate when people are like [putting on an obnoxious voice ], "The pandemic was a gift," because it killed everyone and decimated everything. But when everything halted, I took it as a sign to go do something else. I had always thought of myself as a director, but I didn't think it was going to happen. I moved to Los Angeles and was going to work in politics.

I really credit two artistic directors for changing that: Danny Feldman at Pasadena Playhouse, and Pam MacKinnon at American Conservatory Theater in San Francisco. They both gave me really big opportunities to direct on a giant canvas [with Head Over Heels at the Pasadena Playhouse, and The Wizard of Oz at A.C.T., respectively]. And that is what coaxed me out.

I also made a very conscious choice, coming out of the pandemic, that I just wasn't going to choreograph anymore. Though I did twist myself out of retirement to choreograph Here We Are, because you don't say no to the final Stephen Sondheim musical!

Sims: How did these two solo shows, the autobiographical ta-da! by Josh Sharp, best known as the cocreator and costar of Dicks: The Musical, and Can I Be Frank?, a tribute to the late pioneering stand-up Frank Maya by Morgan Bassichis, come into your life?

Pinkleton: Josh Sharp invited me to a work in progress of ta-da! At the time, he was just like: "It's me and a bunch of slides."

Sims: 2,000 PowerPoint slides, I believe!

Pinkleton: At the time it was like 1,200 slides. I went to this comedy club in Brooklyn, knowing nothing, and laughed the hardest I've ever laughed. And the secret of Josh Sharp, his razor blade inside of the cupcake, is that it is also deeply, deeply moving.

As for Can I Be Frank?, me and Morgan both have a tremendous interest not only in stupid comedy, but also the beautiful and devastating time between 1982 and 1996 in downtown Manhattan. The idea he was working on, about the life of an openly gay comedian from that time named Frank Maya, struck upon themes that are deeply personal to me. Morgan finds this crazy combination of surprising comedy and fierce political force. To be able to hold what they're holding historically with the show but also be as funny as they are—they are absolutely one in a million.

Sims: Maya passed away from AIDS-related complications in 1995, just one of many amazing artists who died young during that era.

Pinkleton: The show asks us to look back at all those genius artists that we lost, and to imagine what we would have today if we hadn't lost them. Imagine the art we would have. These guys would be 65 years old right now. But it's also just a really good time in the theatre, as I hope all my work is!

Sims: All your work is so joyful and alive and always prioritizes giving audiences a good time. But as in so much queer-infused work, I feel like that history of loss is always lurking under the surface.

Pinkleton: Totally. I am super death obsessed. We are surrounded by loss and death at every moment—it's just a choice of whether you want to engage with it or not. And I've dealt with a pretty extraordinary amount of loss and death myself for a 38-year-old. I do think there's death underneath everything joyous, whether that's a play, or a meal with friends or going out dancing. I go out dancing to be reminded that I'm not dead.

It is a cliché to say, "Life is short y'all, so live up what ya got," but I do think that is the point of theatre. Theatre holds those highs and lows really well. And that is—spoiler alert—very much what ta-da! is about. We're telling the world that ta-da! is about a gay guy being funny, but it's actually super-duper about death.

Maybe we just keep making the same shows over and over again… I hope not. But I at least keep trying to solve the same problem over and over again or untangle the same question. And that is: How can you live as joyously as possible, knowing that our time is temporary, and that at any moment, it could all go away?

This interview has been lightly edited for length and clarity.

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TDF MEMBERS: At press time, discount tickets were available for Can I Be Frank? Go here to browse our latest discounts for dance, theatre and concerts.

Oh, Mary! is occasionally available at our TKTS Discount Booths.