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Vivek Shraya's one-woman show How to Fail as a Popstar is directed by Brendan Healy, artistic director at Buddies in Bad Times from 2009 to 2015.Heather Saitz

It was the morning after Vivek Shraya’s second performance of her one-woman show, How to Fail as a Popstar, and the poet/memoirist/novelist/visual artist/singer-songwriter/professor was talking about her theatre debut and confronting the rigors and reality of being a theatre artist.

“I jump a lot from genre to genre, medium to medium. Even when I do a reading, I’m usually off the book; I do monologue style. So I was like, I can do theatre,” she says over breakfast in Calgary. “And actually it’s been very humbling.”

The show, which includes a few musical numbers, is an autobiographical account – with some insertions of fantasy – of Shraya’s musical ambitions and career which, to be fair, has not been a total failure. But those musical ambitions did not work out as Shraya had desperately hoped.

Shraya, who turns 39 on Feb. 15, found refuge in pop music, growing up in Edmonton, the child of Indian immigrants. This was long before she came out as trans, and Shraya was often subject to ugly taunts.

“When you’re a young kid and you believe in a dream, that dream is actually quite tangible. There’s a part of you that actually believes. I genuinely believed I was going to make it; I believed these people were my friends. That Courtney Love and I and Michael Stipe we were all related in our past life. And that they were just waiting for me to show up,” she says, 100-per-cent serious. “This is the magic of pop and this is the magic of dreams. And this is the necessity of dreams, especially as a brown queer kid in Edmonton. A lot of it’s survival. And you have to invent this fictional life that’s actually quite real to you.”

She began making music and found champions along the way – not all of whom were healthy. In the show, she describes a toxic professional relationship with a woman in the industry who offered Shraya music industry guidance and a couch to sleep on. Beckoned by “Mama Carla,” Shraya moved to Toronto to try to launch her musical career.

She did have a career – and still does. In 2002, she released Samsara: The Sketches, an indie acoustic project that caught the attention of Tegan and Sara, leading to a friendship and professional collaboration. Tegan sang on Shraya’s 2005 release A Composite of Straight Lines and she opened for them on a U.S. tour that year. She now sits on the board of their foundation. Shraya has a band, Too Attached, with her brother, Shamik Bilgi. Most recently, she has been releasing singles from the play including Music Ur the 1, the show’s theme song, and, on Valentine’s Day, I’m a fag 4 U.

Shraya is pan-genre prolific, but best known for her often autobiographical writing, including the 2018 memoirs I’m Afraid of Men. (That book provoked Buddies in Bad Times founder Sky Gilbert to write a critical open letter and poem I’m Afraid of Woke People in response, which led to a strong backlash against Gilbert.) But Shraya had not written about her pop star ambitions or music career before – a huge part of her life.

The play is directed by Brendan Healy, artistic director at Buddies from 2009 to 2015, whom Shraya has known for a long time. At one point, they discussed possibly adapting her novel She of the Mountains for the stage. That didn’t work out. More recently, Shraya was sharing her Mama Carla stories with some music world colleagues, who were thoroughly entertained. Shraya pitched her failed popstar idea to Healy, who is now artistic director at Canadian Stage, which commissioned the work.

They spent last summer developing the work in Toronto, a gruelling process, Shraya found. She realized quickly that theatre is a very different animal from performing as a musician or doing a reading – both in its development (it is a very collaborative effort) and its execution. One note she kept getting from Healy, the show’s director, was “eyes up, eyes up,” she says. “Because I tend to look at the floor, even when I’m sipping my water.”

The run at Calgary’s High Performance Rodeo – officially a workshop, not the premiere – was the first time she performed it to the general, ticket-buying public.

“I went to bed after the first night literally going through line by line that I messed up,” said Shraya after performance number two. “I was like, ‘I screwed up this line, I screwed up this line, I screwed up this line.’ Just like really self-flagellating. And then I woke up in the morning and I was like, ‘you know the beautiful thing about theatre is I get to do it again. I get to try again.’ ”

She was also wrapping her head around how different each night can be. The first show was sold out, buzzing, electric, with a number of people she knew in the audience. But then on the second night there were laughs for lines that nobody had laughed at before; her performance, she says, felt looser. There were a couple of moments when she came out of character and interacted directly with the audience.

One thing she and Healy had a lot of discussions about was where to end the story. After opening night, she felt good about her decision to end it, at a not particularly high point in her career.

“I think how culturally we’re so obsessed with success. The stories that we hear, the stories that we value, the stories that we celebrate, especially in a capitalist system, are ones about success,” she says. A friend who saw the show made a poignant comment that indicated to Shraya that she is on the right track. “I’ve never seen something that was about so much desire, and so much wanting, and then it not working out,” the friend said.

The story ends roughly 10 years ago. There’s been a whole new chapter since then to Shraya’s artistic life and success. After things didn’t work out with music, she became a writer. Her writing has been nominated for Lambda Awards and longlisted for Canada Reads. She has a new novel, The Subtweet, coming out in April. She has launched an imprint, VS. Books, with Arsenal Pulp Press. She is an assistant professor in creative writing at the University of Calgary. Her visual art project Trisha, in which she posed as her mother in a series of photographs, has travelled North America. And while she might not be anywhere near Madonna status as she had once coveted, she continues to make music. Her 2017 album Part-Time Woman was longlisted for the Polaris Prize.

But ending the show on that kind of high note didn’t feel right.

“Because – and I say this with a lot of respect to the people who care about those parts of my work – those aren’t the things I wanted. I feel very grateful to have an audience that cares about my writing; I’m happy to have a teaching job. But that wasn’t the dream for me,” she says.

“A lot of these other things feel like a consolation prize, an excellent consolation prize, but still.”

How to Fail as a Popstar is at Canadian Stage’s Berkeley Street Upstairs Theatre Feb. 18-Mar. 1 (opening Feb 19).

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