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Teal Dragon breathing orange flames Winging It Improv show poster

ABOUT THE SHOW

Winging It! is an improvised fantasy comedy show in Calgary, AB—think a cross between a TTRPG Actual Play and an improv games night like Whose Line Is It Anyway? Mixing short form and long form improv with a fantasy RPG à la Dungeons & Dragons, this show is a recipe for critical tales and epic fails. Roll the dice! Expect laughter and adventure! Let's have some fun!

 

The show is fully improvised, created live with suggestions from the audience. If you're a fan of fantasy role-playing games this show is for you. If you're not, but you just like laughing, this show is also for you!

 

Each of the shows is a standalone adventure, but they’re also part of a larger story. This means whatever show you come to, you’ll have a great evening of entertainment. If you attend more than one, you’ll be rewarded by seeing the same characters progress through a larger adventure. Either way, come out, have a laugh, have a drink if you want, and get ready for some fun-loving merrymaking.

HOW DOES IT WORK?

Winging It! is an improvised comedy show that mixes long form and short form improv with elements of tabletop role-playing games. The show is run by the Game Master, who acts like the director of an improv show mixed with a dungeon master from Dungeons & Dragons. So how does it work?

Improvised Comedy: The entire story is unscripted. That’s the point! Occasionally, the Game Master or a performers will ask for offers from the audience to help shape the narrative. That way, the audience co-creates the story and the performers can’t plan anything too far in advance. We are, as they say, winging it!

Throughout the show, the Game Master will also set up games for the performers to play. Some of these games may need suggestions from the audience (or even audience participation)! The “rules” of the game don’t truly matter. It’s all about fun.

 

Role-Playing Game: Our cast is made up of two groups. Heroes are characters who work together on an adventure. Each has specific attributes, abilities, and equipment to help them in the challenges they face. Story Knights are the ensemble performers who take on all the other inhabitants of the world. This can be anything from shopkeepers and monsters to doors and trees. Really, anything goes!

Throughout the show, the Game Master will create scenes that involve challenges and encounters for the heroes to face. Sometimes these are overcome by playing improv games. Sometimes the outcome is determined by rolling of a twenty-sided die. When a performer rolls the die, the Game Master decides how difficult the challenge is by assigning it a number between one and twenty. If the die roll equals that number or higher, they succeed! If not, they fail and suffer the consequences...

The Audience: This could be you! Their only job is to sit back and enjoy the show. Make suggestions when called upon if you want. Clap, cheer, laugh, and have a good time.

Rolling the die sounds fun, doesn’t it? Well, we have good news for you: you can take part. For each show, we sell a limited number of Re-roll Tokens. Audience members can purchase these before the show or at intermission. Then any time a die roll occurs during the performance, they can “spend” the token to have the performer roll the die again and take the second result. For better or for worse.

There’s a bunch of others rules, but the Game Master will either explain them as they go or leave you to figure them out. Thank you for coming and remember: life can be an adventure as long as you’re Winging It!

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© 2025. Winging It Productions.

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