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Cast members Chris D'Silva, Adrian Pavone and Vivek Shraya pose at the Cameron House in Toronto to promote Vivek Shraya’s new comedy 'How to Fail as a Popstar’ on Sept. 22. The Cameron House is significant Shraya because her first show when she moved to Toronto was at the venue.Jennifer Roberts/The Globe and Mail

On the morning of a brutal snowstorm in early February, the cast and crew of the new CBC Gem series How to Fail as a Popstar headed to Sheridan Centre, a Mississauga mall that feels as if it’s been frozen in time since the 1990s. That’s appropriate, since it’s standing in for an Edmonton mall where artist, musician and writer Vivek Shraya got her first taste of rejection as a young teen participating in a talent show.

That heartbreaking moment comes to life again when the cameras turn on, this time with Shraya, now 42, in more control. The new series is an adaptation of her 2020 one-woman play and book, about her lifelong dreams of becoming “a brown Madonna,” only to be hit with obstacle after obstacle. She not only wrote the adaptation, but co-stars, and directs an episode.

How to Fail as a Popstar is the kind of story we don’t often get to hear: the ambitious idea that never landed, the money down the drain, the big break that doesn’t come. “Anti-success stories exist. Having a talent and putting in the hours won’t always take you to the finish line,” Shraya says.

Shraya did eventually chart her own path, and has produced many multidisciplinary projects. Over the past two decades, she’s released a dozen solo albums – and two more with her band, Too Attached, which she formed with her brother Shamik Bilgi in 2015. She’s toured all over North America. She has also written several books, including novels, a poetry collection and an autobiographical graphic novel. No stranger to both the big and small screen, she previously created a series of short films, and composed the music for CBC Gem comedy series Sort Of, for which she won a Canadian Screen Award earlier this year.

All of this might sound like a success story, but Shraya could never quite break beyond the limits of Canadian fame. She condensed that struggle in How to Fail as a Popstar, the play, which debuted in February, 2020; it was adapted, almost word for word, into a book a year later. She toured the play until this past winter.

Taking the format of a diary read aloud, the play ends with Shraya sharing 40 reasons for why she failed as a popstar: “I was born in Edmonton. … My parents are immigrants. … No one invested a million dollars in me. … I don’t own leather pants. … I’m brown and queer and trans …”

When Sphere Media came calling to adapt the play, the story took on a narrative format for the eight 15-minute episodes, all written by Shraya and directed by Vanessa Matsui. This iteration remains autobiographical, but includes three versions of Shraya: the young high-schooler (Chris D’Silva), the motivated twentysomething (Adrian Pavone), and a dream-like, guardian angel version of present-day Shraya, played by her 42-year-old self, who narrates and dispenses wisdom to her younger counterparts.

The show was shot in just two weeks. The crew was a diverse one, and largely female. That was an intentional choice, as Shraya worked hard to ensure the set veered away from the “dude energy” of the music industry in which she’s long been immersed. She even pointedly asked the few men who were hired: “How do you feel about all these women of colour being in leadership positions? Are you going to be able to handle that?” Matsui said that dialogue helped significantly to create a respectful on-set dynamic.

For D’Silva, who was shy while off the set but very much alive while a part of it, it was “a different thing getting to play a real person, so I do feel a little bit of pressure, but honestly, I’m just having so much fun.” (The nerves really only reappeared during the choreography – which he nailed).

Director Matsui, who saw the play before she began production on the CBC series, was surprised how much she related to the star, thanks to having been on a similar journey to the one Shraya took; Matsui originally dreamt of being a full-time Hollywood actor, though her resume remains largely Canadian-made.

“With Vivek’s work ethic and her superkind personality, it was exactly the kind of person I want to be working with in my life,” Matsui said. “And as a director, it’s always great when you can have the creator on set with you because, inevitably, things go awry on set; anything can happen. Having someone who knows the project inside and out is really helpful. She’s also got impeccable taste.”

Shraya insists it’s been a team effort. “Everybody is so good at what they do,” she says. “I’m not used to it. I’m used to doing everything myself. As a creative, especially as a marginalized person, a lot falls on you. So for me, this experience has been less about telling my story, and more about being in a collaborative collective.”

The production team’s passion for the story is evident in the details. Shraya offered up a trove of childhood photos as reference for make-up artist Fatema Hoque and costume designer Tala Kamea, who together created a kind of aesthetic code for the series’ narrative timeline. Young Vivek, who is still discovering his identity, dons a uniform of T-shirt and jeans, but with little pops of colour that hint at what’s to come. Adult Vivek, who escapes Edmonton and is coming into his own, opts for tighter jeans, more exposed skin, a whole lot of leather, and always wears a choker. Dream Vivek, on the other hand, is out and proud in star-worthy gold and glitter.

Nothing gives way to cliché or stereotype. Take, for example, Vivek’s mother (Ayesha Mansur Gonsalves), who is not your run-of-the-mill salwar kameez-wearing, bun-sporting mum. Like Dream Vivek (who finds inspiration in her mother), she’s self-assured and walks her own path. She likes a bright lipstick, wears her hair out and down, and loves a good pair of jeans. She also doesn’t ceaselessly admonish her child for choosing a creative path. All of which is to say: Mrs. Shraya doesn’t follow any of the brown mom patterns.

“That’s why it’s so important to have brown people in hair, make-up, and costume; they know what it means to have a non-white body, what it means for us to dress and look a certain way, why and what it can say,” Shraya says.

Not only did Shraya leave her touch on everything from make-up to wardrobe, but her multitalents have helped kickstart an empire of sorts in conjunction with the series. She has released a soundtrack, which includes new songs and remixes of her older ones, including a feature with Jully Black. There’s also limited-edition apparel, including a T-shirt that reads “Failed Popstar,” to go along with the series’ release.

After telling her own story countless times onstage, this latest version has been an emotional ride for Shraya. “It’s so weird when you see your life play out in front of you, when someone else is saying the words or wearing the clothes or singing the songs.” It’s been emotional, too, for the show’s cast and crew, who Shraya says all found their own ways into her story, because “there are limitations in finding spaces where we can think and talk about failure.”

It seems right, then, to call this a success story – and Shraya’s on board with that. “To have made it the way I wanted to, with a diverse and creative group of people? It’s badass,” she says. “We’re living in the future over here.”

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