When Lara Rae helped launch the Winnipeg Comedy Festival nearly two decades ago, there weren't a lot of options for people who wanted to see live comedy in the city, she says.

"There was Rumor's Comedy Club and that was about it, and so it felt like there was room" for a festival dedicated to stand-up, said Rae. "There was elbow room in the market."

Turned out, there was.

The festival, which debuted in 2002, begins its 18th season on Sunday night, running until May 4. It's also the last year Rae, 55, will serve as artistic director.

"I'm obviously very proud of … the fact that it has continued, you know. I really am," she said.

"I think that looking back over the 18 years, we've produced an extraordinary amount of memorable comedy and, you know, given … opportunities to people who might not have had opportunities."

Winnipeg comedian Lara Rae co-founded the Winnipeg Comedy Festival and has been its artistic director since 2002. (CBC)

Comedy and the ability to make people laugh have been part of Rae's identity since she was a kid. Born in Glasgow, Scotland, she had moved to Canada by age 19 and was performing as a stand-up comic in Toronto, while attending York University.

"One of the ways I was able to fit in was by cultivating my intelligence and by cultivating my sense of humour, and that made me popular to some degree," said Rae, who eventually turned that into a decades-long, award-winning career that's seen her perform around the world, and made her a staple in Winnipeg's comedy scene.

She moved to Winnipeg in the mid-1990s and started collaborating with CBC Radio producer Tom Anniko. Rae and Anniko had already worked together on a number of comedy shows when they pitched the concept of a weekend-long festival that could be recorded and aired on CBC Radio.

They teamed up with with the Gas Station Arts Centre in Winnipeg's Osborne Village, and the idea took off.

Not only did festival shows air on radio, but a number of the gala shows were recorded and aired on CBC Television.

"It was all quite overwhelming when it … came off so well," said Rae, who saw the festival as an opportunity to bring comics she knew and respected to Winnipeg, and also create work for herself and other performers.

The festival, which started with roughly 10 or 12 shows in 2002, has become a fixture in the city's comedy scene. This year the lineup includes more than 70 comics and 30 shows at venues around the city.

Rae said watching the annual festival become part of the city's landscape, alongside more established events like the Winnipeg Fringe Theatre Festival and Winnipeg Folk Festival, has been tremendously rewarding.

"The city has given me so much as a human being," said Rae. "It was just nice to give something back."

A voice for comedians

Giving a voice to people who weren't getting opportunities is also something Rae said was important for Winnipeg Comedy Festival organizers from the beginning.

"Even though there were not that many women in comedy, you know, we worked very hard to make sure that the women that were in comedy did have equal opportunities."

Rae says she'll focus on writing, performing and teaching after she leaves the comedy festival. (Submitted by Nick Kowalchuk)

Rae, who is transgender, has watched the comedy scene evolve. She began performing as a transgender woman about four years ago.

"As difficult as that was, it was made much easier by how many people … had made those demands in the past," she said. "I did not need to, quote-unquote, 'win them over' to who I was as a person. I only needed to win them over to my talent."

Although she hadn't made her gender transition in the festival's early days, "maybe I was a small part of making the comedy scene easier for people like me … ironically. But more than that it was the comics themselves, the incredible comics that came up before me."

'Ahead of the curve'

Rae said what she sees now is diversity across the board, including in comedians' gender, backgrounds and their subject matter.

"I have seen this evolution and now … I think it's time for this evolution to continue with younger and newer voices," she said.

Taking the reins as artistic director is Dean Jenkinson, another staple of Winnipeg's comedy scene.

He's been involved with the festival since it started.

Dean Jenkinson, left, and Rae will both be performing at the Winnipeg Comedy Festival this year. Jenkinson will take over as the festival's artistic director. (Submitted by Dean Jenkinson )

"When I think about watching Lara do comedy, I'm kind of reminded of the phrase from diving — 'degree of difficulty,'" he said.

"Anybody can jump off a diving board into the water, but you get points for how complex and how difficult the attempt was, and she goes for very high-hanging fruit."

In addition to what she brings to the stage as a performer, Jenkinson said the creation of the festival has given hundreds of comedians a platform and helped put Winnipeg's comedy scene on the map nationally. He said Rae has also brought a real sense of inclusion and openness.

"It used to be if you'd go see an open-mic night, it would just be one white dude after another. And now diversity and representation — we're starting to realize very late how important those things are, and Lara is somebody who has been ahead of the curve on that," said Jenkinson.

Tom Anniko, who helped spearhead the festival with Rae, was working as executive producer for radio comedy and drama for CBC at the time.

"Part of the reason for the festival is it was a place to try out new shows.… I was trying to develop shows for the radio, so The Debaters came out of the comedy festival," said Anniko.

"There were numerous other pilots and specials and things that really happened because of the festival. It was just such a great way to connect the CBC and comics."

Tom Anniko was working as a producer with CBC Radio when he helped launch the Winnipeg Comedy Festival with Rae. (John Kristalovich)

Anniko, who has since retired from CBC, calls his involvement in the creation of the festival one of the highlights of his career.

"I was, and am, extremely proud of it," said Anniko.

He said the fact Rae has been able to continue developing it over 18 years is extraordinary.

"I really think Lara's quite brilliant as an artist and as a … conceptual thinker and writer," said Anniko.

Rae said she plans to focus on writing, performing and teaching after she steps away from the comedy festival. Leaving it behind won't be easy.

"At 18, it's like a kid that's moving out of the house," she said.

"It's moving out of my house and going off on its own. I mean, that's kind of how it is."