Siobhan Thompson is ready to take on a bruiser in Dimension 20’s latest season – and to face down the Hollywood Bowl. A veteran of College Humor and the Rick & Morty writer’s room, Thompson has also become one of the fixtures of the Dropout comedy series. Typically, Thompson’s characters are more mystical and intellectual in nature, relying on clever tactics and spells.

That’s partly what excited her the most about her part in Cloudward, Ho!, which brings a steampunk touch to the TTRPG show. During an interview with TVBrittanyF, Siobhan discussed the joys of playing outside of type, the unique approach to finding natural comedy the show, and her expectations heading into the Hollywood Bowl live show.

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TVBrittanyF: Typically, you play the more cerebral characters in Dimension 20, your scrappy stoat in Burrow’s End. This season is a bit different because you’re playing the much more brawny Vanellope Chapman.

Siobhan Thompson: That was a big fun challenge for me. This season, it was like, ‘let me play Vinnie Jones, but a girl.’ I think it was really fun to play like a strong guy and somebody who is certainly not stupid, but she’s not intellectual. She’s very straightforward, very reactive to what is happening right in front of her. She’s very loyal, trusting of everybody. A stand up kind of guy. It was really fun. I really enjoyed it.

Playing that kind of archetype can be a lot of fun. What was the character development like, figuring this character out? I’m always fascinated by how you and the cast work out the directions of the characters.

Brennan sent us all a big lore doc that was mostly world-building. Here are all these different towns and cities and countries and political things that are going on in the world. And then, hey, you’re a former member of the crew of this ship. It became about thinking about pirate things and the actual roles of sailors aboard a ship.

The bosun is such an important member of the crew because the bosun is basically the person who tells everybody what to do. They are the person who is taking the captain’s orders and relaying it to the others. I don’t know, for some reason, that just really tickled me. It really excited me to play that. I watched Master and Commander, which I rewatched to get in the zone for this.

First and foremost, Dimension 20 is a funny show — but it’s also one that blends a lot of different genres and tones into the stories through the natural evolution of a character. Does that versatility and flexibility play into your approach to character creation and development?

These sorts of adventure stories aren’t necessarily haha funny, but they are comedic. There’s some very funny moments in Indiana Jones, like the most obvious one that I can think of, just off the top of my head, is when he’s squaring off to that Nazi, having just beat up a bunch of them, and then he just pulls out his gun and kills him. That’s so funny. I think that it is finding moments within the genre to do that — it’s sort of the same way we wrote on Rick and Morty. In Rick and Morty, we were never thinking about jokes.

We don’t talk about funny stuff at all. It’s a lot like, hey, let’s just talk about the nature of memory for a week. It was much more of a science fiction writing room where everybody in the room was funny. You don’t have to think about the jokes at all, because the funny will happen. The thing that makes it unusual is the genre and storytelling. I don’t worry too much about being funny, because I am funny, and I know that everybody else is funny and that we make each other funnier, and often the funniest thing is just doubling down to the genre and being as honest an actor as you can be.

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What has been the biggest surprise of the season?

I mean, I don’t think that at this point I’m surprised how brilliant my friends are, but I am always amazed by it. We did a fun thing this season with rumors, where everybody wrote some true and some false rumors about themselves, and then Brennen wrote some as well, and then handed them out to everybody. So everybody had a little stack of rumors that might or might not be a lie. And that was such a fun mechanic, I think.

We also have to talk about the upcoming live show at the Hollywood Bowl! After the success of the Madison Square Garden show earlier this year, what are you keeping in mind ahead of this one?

There’s a lot of sort of backstage logistical stuff, which I think is an inevitability. There’s a learning curve of playing venues that we’re all still learning. It’s a lot of the Dimension 20 staff learning this alongside us. I think for me, the most important thing that I have to focus on is just making sure that I’m prepared enough that I can go out there and be fully present and not worry about what it is that I’m supposed to be doing when I’m up there. Adaine is level 14, I have to spend a couple of hours going through and reexamining my little books of everything.

Dimension 20: Cloudward, Ho! debuts on June 4th on Dropout. Tickets are now available for Dimension 20 Live at the Hollywood Bowl on June 1st.

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