What do you get when you mash up Whose Line Is It Anyway? with a live-action Dungeons & Dragons campaign? You get Winging It — Calgary’s improvised fantasy comedy, back this fall for a brand-new season of monsters, heroes, mayhem, and distracting side quests.
Director Andrew G. Cooper calls it “really like a combination of short form improv with games like you would see on shows like Whose Line Is It Anyways? or if you go to like a theater sports show, and then we’re combining that with like a TTRPG actual play. So like if you listen to podcasts of people playing D&D, it’s sort of like that too. We’re like taking those things and combining them and creating something totally new”
If you know DnD, you already know a bit about improv. But, if you know improv and not DnD, no sweat. The show is designed for both active listeners and active participants.
Each two-hour performance is built like a campaign module, or a level in a game, or a chapter in a book, where a group of travellers are presented with a quest and plenty of challenges. Sometimes the heroes roll dice to see if they can make it across a broken bridge. Other times, they’re stuck in a troll’s riddle game where the only way forward is to win an improv challenge.
“The whole show is two hours,” Cooper explains. “We do a full show, people are going to come out and get their money’s worth”.
Like any good campaign, this one’s been tweaked for balance- and like any good improv game, leaves plenty of space for audience generated chaos. Last year’s re-roll tokens are back, but stronger. For the uninitiated, the re-roll tokens allow audience members to directly affect the action on stage.
“We buffed it,” Cooper says. “We made the audience token stronger and it makes more of an impact, which I think is great”
The audience doesn’t just influence the adventure in the room. Between shows, fans vote online to decide where the heroes go next.
“So they would see the poll, they would do their voting online, and then they would get to come and see like, ‘Oh yeah, the decisions that they kind of made collectively — that really makes a big impact on the show,” Cooper adds.
Heading into the second season, it is clear that both audiences and performers love the concept. Cooper says auditions were fierce, they could not even see everyone who applied and last season saw several sold out shows.
“Coming out of the pandemic and just the way the world is right now with, you know, generative AI, I think that people are really looking for community and looking for something that’s like, real, live, and tactile,” he adds.
Ticket information can be found here.
Campaign #2 show dates
Theatre 1308 | 1308 Edmonton Trail NE, Calgary
- September 20, 2025 – 8PM
- October 11, 2025 – 8PM
- October 25, 2025 – 8PM
- November 15, 2025 – 8PM
- November 29, 2025 – 8PM
- December 6, 2025 – 8PM