The Unsleeping City is just one of the settings established in Dimension 20, the TTRPG comedy show streamed by Dropout. With the magical underbelly of New York City providing plenty of comedic twists and turns, The Unsleeping City turned out to be a deceptively emotional 2-season storyline about the Dream Team and their efforts to protect their community. This includes Ally Beardlsey and Lou Wilson, two of Dimension 20‘s most consistent stars.

BrittanyTVF got the chance to sit down with the two performers ahead of the Gauntlet at the Garden, which brought back The Unsleeping City for a sold out event held at Madison Square Garden on January 24th. Both Lou Wilson and Ally Beardlsey looked back at what stands out about their characters from The Unsleeping City, returning to one of their earliest settings, and which universe they’d most want to see brought to the live format.

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Ally Beardlsey and Lou Wilson sit down with BrittanyTVF to discuss The Unsleeping City and bringing the characters back for Gauntlet at the Garden.

BrittanyTVF: The Unsleeping City was one of the earliest campaigns of Dimension 20, and it has been four years since season 2. What was it like stepping back into these characters?

Ally Beardlsey: This is one of my favorite seasons. I’m having a great time. I’m really excited to go back to the themes and these characters and their relationship. So I’m just truly so happy.

Lou Wilson: I think these characters are so endearing. I mean, I think there’s just so much around in this world, so much around dream and community that is so beautiful. I think particularly at this time in America, it is really nice to be asked to take back on the mindset of these characters who care so deeply for taking care of each other. I think there is something really profound about playing these characters again in 2025.

Ally, you got to replay Peter in the Time Quangle, but Lou never got the chance to revisit Kingston. Now coming back to the character fully for Gauntlet In The Garden, are you happy or sad you didn’t get that chance to revisit?

Lou: it’s interesting. I have been rewatching [The Unsleeping City] to get ready for the show. I do think I had built up this version of Kingston in my head that was very much, “Kingston, Man of the City.” Watching it again, I’m so loose. It is just a free-flowing thing. That sense of community and that weight and that stewardship comes through in a very playful, human way.

I think that was something I’m glad I didn’t actually do [during “The Time Quangle.”] I think I would have been like, this is Kingston Brown, sepia-toned and half shadow on the face. There’s something to how is alive and playful and lively and fun on top of doing these incredibly profound things and carrying within these incredibly profound themes.

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Coming back to these characters, what would you say surprised you the most about these characters?

Lou: I think for Kingston, I started with such a simple core of a character. I think, just because the depth of my understanding D&D was not as profound as it is now, I just wanted to play a city cleric. It was this Unearthed Arcana little side sub class that I thought was like, ‘oh, this is cool for magical realism.’ I was like, oh, and he’s a nurse. I was never like, ‘Brennan, it would be cool to play the Voice of the People!’ But all of these things came to be true of him. I think when Kingston met Pete, the concert of Kingston the Vox Populi and Pete the Vox Phantasma, I think the character grew into something so much richer and deeper than I ever expected.

I think, especially in season two, I was genuinely surprised when it kind of became this story of Kingston tapping into this thing he had always wanted, which was to be a father. I think that’s something I knew of Kingston, but I didn’t know when or if it would come out. I think it truly came out of, when Brennan asked me what would make Kingston fly, what thoughts like lift him up. That’s when it became a through line. So I don’t know. I think the entire journey of Kingston has really been a surprising one. I think what I started with was so small, and I think that just speaks to the collaborative process with Ally and with Brennan to kind of make Kingston into the Kingston that we know and love totally.

Ally: I kind of feel similarly, because with Pete, the story I was telling was kind of a very common queer story. Of the runaway going to the big city from the small town. I think the emphasis on community and connection showed Pete that he needed to kind heal himself, to be a helpful member of the community that he has entered that was nice enough to take him in. I think that kind of happens when you run away to LA.

You’re not involved in what’s happening. You say weird shit about people who are experiencing homelessness, and you’re just talking about acting, but there’s a full community that you could tap into. I wasn’t expecting to explore that at all. I do feel like Pete was this story of a transplant who decides to plug in, and the only way you can do that is to really look at yourself in the mirror.

For Pete, that included sobriety and the whole second-season arc. But I think I wouldn’t have had that without the mirror of everybody else at the table wanting to play a story about connection and friendship. You can’t do it alone. The nature of the game is like, who on earth wants to sit there while six different scenes are narrated where the person is alone? No, we all have to be in the same spot. So it does kind of pull everyone together. You start looking for the strands of connection.

What other setting or season would you want to revisit in a live setting like this?

Lou: It would be really sick if we could just get 20,000 people together to cry while we played Crown of Candy. Like, Brennan just narrated some beautiful death scene and you have 20,000 people grabbing each other’s shoulders too hard.

Ally: Oh my God, at the Sydney Opera House!

Lou: [Laughter] While the Philharmonic plays behind us with this beautiful score, and as nougat pours out of this marshmallow man.

ALLY: It’s super fucked up, but it’s so real. [Laughter]

Dimension 20 is now streaming on Dropout

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