Alex Stompoly

Immersive theater, improv comedy, drag, and Dungeons & Dragons collide in The Twenty-Sided Tavern, an internationally acclaimed show where the audience becomes the fourth player in a one-of-a-kind adventure.

Since premiering in New York City in May 2024, The Twenty-Sided Tavern has enchanted adventurers worldwide, even making its international debut at the Sydney Opera House later that year. Variety praised the “cacophony of huzzahs from the crowd,” while Nerdist called it “RIP-ROARINGLY FUNNY.” Rolling Stone declared it “a show that weaves the unpredictability of improv and the game itself into a feat of controlled chaos.”

The all-new production is playing at Broadway In Chicago’s Broadway Playhouse at Water Tower Place (175 E. Chestnut St., Chicago) through September 28.

At the heart of this chaos is Alex Stompoly — actor, comedian, and self-described "Renaissance Drag Queen." We caught up with Alex for a quick Q&A to talk about improv, drag, dice, and what it’s like to perform in a show where no two nights are the same.

GoPride: On Instagram and on your website, you describe yourself as an actor, comedian, and Renaissance drag queen. Which of those three identities shows up the most when you step into The Twenty-Sided Tavern?

Alex Stompoly; credit: André Chung

Alex: You know what, I think it’s actually a happy marriage of all three. The improv is the primary, the leading forefront in that relationship, just because we have no idea what we’re doing, when we’re gonna do it, and how it’s gonna pan out. That’s where the active brain kind of kicks in to add a second support system when I start to waver and I’m like, oh no, what do we say we’re going to do? And then the final bit, which is where my sass and snarkiness come from, is being a Renaissance fair drag artist.

Q: How would you describe the energy of The Twenty-Sided Tavern in one sentence? Is it a comedy, quest, game night, or chaotic mix of everything?

Alex: I think you just gave the perfect sentence right there, truthfully. It’s an electrifying chaotic game night, if I was to really put a pinpoint on it. It is getting together with all of your friends in one room and just having that absolute blowout of a game that I think we all wish we could do on a regular basis.

Q: The audience becomes the fourth player in the show. What’s the wildest or most unexpected choice you’ve ever seen them make?

Alex: For me, it's always those moments where an audience will openly decide to bring a character more to the front door of danger, in a very fun way. I think they crave those moments of seeing someone go through trials and tribulations, and if we as a cast can see a way to maybe not get around it, but to do it in a more polite way, the audience will absolutely go chaotic and say, no, we want to see it happen, and we want to see it happen in a really grandiose suffering kind of way. And we’re like, OK, we can do that too. That’s fine. If that’s what you want, we’re here for it.

Q: How do you keep yourself flexible as a performer, especially when the dice and the audience can throw you in any direction whatsoever?

Alex: I think the phrase, and I often mess it up, but I think it's "love tightly, let go lightly," where nothing to us is more precious than the story we are telling with our audience and the time that they are also having. We may be up there playing Dungeons and Dragons and having a great time, and we love being together as the five people on the stage, but at the same time we recognize fully that it’s about the experience that our fourth adventurer, our audience, is coming in to have. We have to consult them and be on their side as much as we are on ours. We may have a great idea, but if they propose something different, something better, or just something they really want to see and are invested in, we have to be prepared to say, cool, those are the needs of that other cast member we’re meeting. So let’s do it. We’ll be up here again - they may only be in the audience one time. Let’s make this the best thing for them.

Q: Do you have a personal favorite character to embody, or one that feels closest to you?

Alex: In my track that I live in in the show, I rotate between being the Dungeon Master and the Tavern Keeper, so I usually am just facilitating the gameplay. When I’m the Tavern Keeper, I’m the rules lawyer and I’m there to play maybe some NPCs and help guide the adventurers. When I’m the DM, I get to step in and play a more pivotal role in the storytelling. I love being the Tavern Keeper though, because I get to enjoy the show much like the audience does. I’m in the throngs of working and arbitrating rules, and then I hear the nonsense that’s said to me on stage and I get to react without being encumbered by a story. I get the privilege of having an honest response to whatever my castmates do in a given moment.

Q: As someone with a drag background, how do you bring camp, glamour, and theatricality into this fantasy world of Dungeons and Dragons?

Alex: One of the things about Dungeons and Dragons that I’ve always loved, and any tabletop role-playing game really, is there is a pride and an emphasis on being one’s authentic self. Whether that is intentional or not when you’re getting into it, these worlds of fantasy and adventure and allowing you to build a character and embody something completely different, they really do allow you to tap into a version of yourself that you may not get to lead with every day. For me, that tends to be a more authentic version, something I’d really like to see manifest. At the Tavern, that’s what I lead with. When I’m in my element, it is being unencumbered by any sort of manufactured version of what some aspects of society would find more palatable. I’m like, no, no — we’re gonna live in this very real, very camp version of me, because that’s what feels good. That’s what I like.

Q: Were you a Dungeons and Dragons player before joining the show, or did the Tavern become your introduction to the game?

Alex: I was a very light player before I joined. I worked at a Renaissance fair for a long time, and in my tenure there, a lot of my castmates played. I had known of the game — my dad played when I was growing up. I had both a love and aversion to everything my parents enjoyed when I was a kid. I had his manuals and everything, but I played again in my young adult life and fell into it. Combining that with my improv, I found the Tavern, and now I’m very entrenched in it.

Q: What’s one moment in the show where you secretly feel like you’re back at the table playing with friends rather than on stage in front of hundreds of people?

DUNGEONS & DRAGONS The Twenty- Sided Tavern; credit: André Chung

Alex: This usually manifests during combat, when my players are going up against the big bad evil guy and everyone is determined to come out victorious. It’s this generation of ideas and thoughts and hearing my castmates say, "OK, walk with me on this. This is what I want to do. How can we make this work?" In those moments you know people are in the audience, but your vision becomes very focused on the people on stage trying to get their wants and needs to the finish line. It feels just like when you’re back playing with your friends and everyone’s casting ideas off of one another to be successful in overcoming the obstacle and getting to the next goal. Those are the moments where it feels the most like playing at a kitchen table.

Q: If your real-life self were a D&D character sheet, what would your highest stat be?

Alex: Oh, it would absolutely be Charisma. I’m dripping with it. I can tell — I’m loving this interview with you. It would absolutely be Charisma, and I’d like to believe it would be Wisdom afterwards, just with everything I’ve experienced. Let it all fall down from there.

Q: Do you feel the show helps bring new people into the world of Dungeons and Dragons who might not otherwise sit down with dice and character sheets?

Alex: I really do. It is truly a show that is for everybody. We get through what rules of D&D we’re going to touch on in the first 10 minutes and boil it down to "high number good, low number bad." Everything else is like watching a more hyperbolic and grandiose Lord of the Rings-esque adventure. You’re just embarking on a journey with these people, and there are small mechanics. We’ve had several instances over the year we’ve been together where people come because it was a gift for a loved one. Someone might say, "I bought it for my partner who plays D&D, and I’ve never been before." They may have had no knowledge of what was going on, but still had a fantastic time and then were excited to return. That’s one of the things I love about this: yes, there is a game being played, but we make it so accessible that no prior knowledge is required.

Q: Where did you find your passion for theater or drag performance, and how did you get into it?

Alex Stompoly; credit: alexstompoly.com

Alex: As cliché as it sounds, I have always been a theatrically inclined kid, and I have the home movies to prove it. My parents would often talk about when I was younger, I would watch The New Adventures of Winnie the Pooh and then act it out in front of the television. When I started school, around middle school, I did speech and debate performance in the Midwest, and it just kept going from there. In high school I got more of a taste of it and did all of the musicals and plays I could get my hands on. That became my undergrad degree from Missouri State because I was a performance major.

Then I found drag. We used to watch RuPaul’s Drag Race on Logo late at night when I was growing up, and I thought it was a brilliant form of expression. It’s theater you can do without waiting for someone to cast you. I fell into that and it has always stayed a part of me well into my professional career. Thankfully, I’ve been able to find positions where my queerness has been integrated seamlessly, and that’s been very important to me. Everything in my professional resume moving forward — either the characters have been queer, queer-adjacent if the performance allowed, or drag queens that have allowed me to keep going.

Q: If you could design your own fantasy tavern in real life, what would be on the menu?

Alex: What a great question. On the menu? There’s probably going to be some sort of handheld pie. That feels appropriate. I like a full meal and something you can eat with your hands without getting too messy. It would be very customizable when people come to visit this well-established business I have. And a gin and soda, because if you ever overhear me at a bar, it’s the only thing that I order.

Q: For the final roll, if you had to sum up the Tavern experience for audiences in one word, what’s your critical hit?

Alex: Hysterical.

PERFORMANCE SCHEDULE
Performances are Tuesday through Thursday at 7:00 p.m., Fridays at 7:30 p.m., Saturdays at 2:00 p.m. & 7:30 p.m., and
Sundays at 1:00 p.m. and 6:30 p.m

TICKET INFORMATION
Individual tickets for DUNGEONS & DRAGONS The Twenty-Sided Tavern are on sale now and range from $50.00 -
$70.00 with a select number of premium tickets available. Additional fees apply for online purchases. Tickets are
available now for groups of 10 or more by calling Broadway In Chicago Group Sales at (312) 977-1710 or emailing
GroupSales@BroadwayInChicago.com. For more information, visit www.BroadwayInChicago.com. As of May 14, based
on availability and subject to change.