When the first Winnipeg Improv Festival happened in 2000, its organizers had no idea what they were doing, or what the festival should look like.

After 25 years of making things up, they’ve mostly got it figured out, says co-artistic director Stephen Sim, who programs the festival with improv artist Caity Curtis.

Featuring a combination of local performers plucked from the Winnipeg alt-comedy universe and a roster of national and international guests, the Winnipeg Improv Festival traverses borders by mashing together new troupes to workshop, develop and present ephemeral, once-in-a-lifetime work to audiences at the Gas Station Arts Centre.

Sim doesn’t remember too many specifics about the first festival — he hardly slept and was in no state to take notes — but by the time the second edition came around, it became apparent that what made things felt “real” was the participation of improvisers from outside the city.

The festival, founded 12 years after the Winnipeg Fringe Theatre Festival and two years before the Winnipeg Comedy Festival, was on an upswing prior to 2020 when the pandemic imposed a hiatus that theatre and performance organizations were among the earliest to adopt.

“It was more than putting things on pause. We knew we had a purpose, still, but we were wrestling with how to serve that purpose when the idea of going out for an evening changed. There was definitely some mutation of our own festival DNA,” Sim says.

The “in-the-room” liveness — the thing that makes improv a worthwhile pursuit for Sim and Curtis — was in peril. And the capacity to welcome visiting species of improv artists was limited: the Gas Station’s comedic laboratory was in code red.

But over the past four years, the improv festival, and its Osborne Village home, have been on the rebound. The Gas Station Arts Centre is in the midst of a large-scale revitalization project, receiving tripartite funding of $800,000 from the civic, provincial and federal governments, fuelling an expansion to its lobby, the development of an interior cafe and wine bar, and improvements to its technical theatrical systems.

The improv community locally has been flourishing, says Sim, with a healthy appetite for improv training by performers and enthusiasts who practice the artform in order to enrich their lives and build teamwork and confidence in their on-stage skillsets.

The Improv Company, co-founded by Sim and Curtis, now welcomes more than 100 students each week to its multi-level training programs. In May, the company, which produces the festival, moved into a new dedicated improv studio in the South Osborne XChange building (421 Mulvey Ave. E).

“Our first round of fall classes just began,” says Sim, who calls the studio the city’s first dedicated improv education space.

And, after a pandemic pause, the festival has once again begun to resemble a lively petri dish of cross-species, cross-border experimentation.

The ability to mix and match comedic communities and voices is what activates each festival’s unique trajectory: visiting artists not only perform with seasoned local artists on stage, but frequently offer expert workshops for improv acolytes who are earlier in their careers, less developed in their stagecraft, or simply interested in witnessing the lightning-in-a-bottle act of collaborative creation.

This year’s improv festival, which begins tonight, draws guest performers from the United Kingdom (Chris Mead and Katy Schutte), Montreal (Kristina Guevarra and Mason Persaud) and Alberta (Red Deer’s Jenna Goldade).

Goldade, an improviser with the company Bullskit, will direct the first act of Friday’s Halloween show, Spooky Scary Skeletons.

Guevarra, a Winnipegger who now runs the English-language improv program at Montreal’s Théâtre Sainte Catherine, will host a free improv workshop on Sunday afternoon for BIPOC community members. The Ecole Kelvin High School-trained improviser belongs to the Montreal troupe Grease Trap, which won best local troupe at this year’s Montreal Sketchfest.

Persaud is a member of the Montreal sketch troupe Tandem Jump, which toured North America this past summer.

Also expected to perform in the ensemble are local improvisers Kevin Ramberran, Kristen Einarson, Jesse Bergen, Kerri Wolosyn, Cuinn Joseph and Mo Gauthier. Musician Mike Turner — a frequent performer with Winnipeg’s Impressions Jazz Group — will provide the tracks behind the laughs.

Barring interstellar turbulence, one more visitor will join the festival while on leave from Starfleet.

Known for playing Sam Kirk — James T.’s younger brother — on Star Trek: Strange New Worlds, actor Dan Jeannotte, in Winnipeg on a film shoot, was a late addition to the lineup.

Jeannotte met Sim years ago at the Winnipeg fringe while performing as a touring artist with Montreal troupe Uncalled For, an act that has won multiple Just For Laughs awards.

The actor — who also appeared in TV series such as The Bold Type and The Good Witch — will take the stage Saturday night as part of the Winnipeg Improv Festival’s Grand Finale Show, a two-act program that begins with newly created work by the festival ensemble and closes with Schutte and Mead’s Project2, a live-improvised science-fiction theatre production.

ben.waldman@winnipegfreepress.com