Fantasy, fireballs, and full-on improv: “Winging It” closes out its season with one last quest in Calgary

You don’t need to know what an initiative roll is to get swept up in the chaos of Winging It.

But it certainly helps if you’ve ever shouted “nat 20!” in triumph.

Part improv comedy, part Dungeons & Dragons-inspired adventure, the fantasy show wraps its first Calgary season with a final performance on May 31 at the Erratics Indie Arts Club — and it’s your last chance (for now) to roll for perception and join the party.

“It is so beautifully nerdy,” laughs director and host Andrew G. Cooper. “We’ve taken short-form improv games and long-form character arcs and mashed them up with the rules and energy of a tabletop RPG. It’s like Whose Line Is It Anyway? met Lord of the Rings.”

Just like any improv show, audience members help shape the journey. But here, the crowd is basically the chaotic neutral bard at the table — shouting out settings, inventing quest items, and even using reroll tokens (available at the concession) to alter the fate of the adventurers mid-show.

The dice are real. The monsters are made up. And the laughter is loud.

“There’s a general outline,” Cooper says. “But the story gets rewritten live onstage, depending on what the audience gives us — and where the players decide to take it. We’ve had dance battles, dice disasters, and even a tiara-themed mission. Each show is totally unique.”

Adventuring parties feature a rotating cast of heroes — some recurring, some one-shot guest stars — as they battle everything from goblins and trolls to bad improv instincts. Every show stands alone, but faithful fans get rewarded with long-term character arcs and callbacks.

And yes, there’s a literal two-foot-tall d20 rolled live onstage. It’s like watching your wildest one-shot come to life — minus the pizza grease.

This final show of the season promises more mayhem, magic, and monster encounters — plus a few last surprises before the company takes a summer break to rest, level up, and prep for the fall campaign.

And if taking Dungeons & Dragons off the couch and onto the stage is your ultimate dream? Auditions are planned for August.

The last Winging It show of the season runs May 31 at 8 p.m. at the Erratics Indie Arts Club (625 11 Ave SW). Tickets and details are online at wingingit.ca