Fantasy is in, in a big way—and for the Dungeons and Dragons-inspired improv theatre show Winging It, that meant sold-out shows and hundreds of guests at their pop-up theatre at this year’s Calgary Expo.
Such was the demand for the shows, or campaigns in the Winging It/Dungeons and Dragons parlance, that Jupiter Theatre is bringing back a second season of shows to close out the year.
“We’re definitely seeing a demand for this sort of show in the city, which is really great because literally hundreds of people are coming out to the Calgary Expo shows, and we filled up shows in our first season,” said Andrew Cooper, Artistic Director for Jupiter Theatre.
“So, we’re just trying to make the show bigger and better than ever, so we can keep meeting the demand of giving people what they want.”
He said that putting on a fantasy-themed show has tapped into that growing interest in fantasy and role-playing games.
“I think just having a show that’s like that helps people feel seen, because the people in the show, the performers, are also just D&D nerds for the most part. I think people in the audience can tell like, ‘oh, this is just people like me getting up there and playing games and being funny,'” said Cooper.
“People feel seen, but it’s also building a sense of community in a way. The other thing that I think is kind of unique about it, which is why I like it, is that we’re really leaning into the fact that it’s a game in that we’re gamifying the experience. So, the audience gets to vote on what they want to do during the show.”
One of those gamification aspects comes right from role-playing games themselves, where a giant dice is rolled to see if the troupe of improv actors succeeds or fails at a particular scene.
“We’ll ask the audience, like we need a suggestion, they’re going to find a location, or they’re going to encounter a monster, and people call it out, and we use those things in the show,” said Cooper.
“People are latching on to what’s called a re-roll token, that people can purchase at our concession. Throughout the show, the performers roll this giant die, and then audience can get them to re-roll it if they want them to give them another chance to succeed. Or, as we’ve seen often, if the performers do succeed a roll, the [audience] gets them to re-roll it again so they fail, which I think is very funny and something I wasn’t expecting.”
Winging It has also begun to build in community polling from social media in between shows, where audiences can vote on what will happen in the next one.
“We’re doing polls of like, where is our adventure going next? So, people will have options: do we want to go to the tower? Are we going to go to a pirate ship? And they vote. I think they want to go see the show because they’re part of deciding where this quest is going and seeing the larger story they’re helping to shape,” said Cooper.
Getting people off their computers and into community
Getting people out to live shows, and building a community around it, has become more important than ever, he said.
“Live experiences, including theatre and music, dance, are more important for people. Especially what I’m finding for younger people who maybe were becoming adults during the pandemic, or their high school years, or their university years, were very isolating,” said Cooper.
“What we’re doing with improv, it’s the new wave of performance for young people. I think they want to be part of things because they’re so used to being part of things on social media and in their online lives. They can now come to a show and be part of it in the same sort of way, but in a live experience with a group of people where you’re all laughing together.”
Familiar faces from season one, Samantha Antonick, Megan Baldry, Kyle Gould, Aurora Moss, Mark Nguyen, James Scott, Oscar Surla, and Ruby Swan, will be returning, while being joined by Danielle Baker, Siobhan Cooney, Jacob Kerslake, and Madeline Hunter Smith.
Cooper said that the characters that audiences had fun with in season one will also be returning, as will the Winging It setting, while being joined by all-new characters from the new performers.
Jordan Smits will also be returning as the lighting and sound director for the show, with some promised improvements to production quality.
Alexa Parker is taking over as the stage manager for Winging It season two.
Shows are being performed at Theatre 1308 on Sept. 20, Oct. 11 and 25, Nov. 15 and 29, and Dec. 6. Tickets are available at www.wingingit.ca.





