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Rupinder Gill

Playback’s 5 to Watch: Rupinder Gill

Following a late career switch, Toronto-based author and writer Rupinder Gill has quickly become a rising star in comedy writing.

When Rupinder Gill decided, at 30, that television publicity was no longer her heart’s desire, she didn’t expect a career in writing full time to come quickly (or easily).

But in an industry always ravenous for fresh new talent, it was in fact exactly what happened.

Encouraged by her friend (and CBC personality) Hannah Sung to meet literary agent Sam Hiyate, who had told Sung he was “looking for funny,” she so dazzled Hiyate he signed her on the spot.

Wasting no time, he encouraged her not to write fiction, which she was already trending towards, but to pursue a memoir about her unconventional childhood growing up in a strict Indian family in Kitchener, Ontario. The idea was forged to recreate childhood experiences she missed out on as a child (Hiyate jokes he wanted to call the book 30 Going on 13) and the resulting 80-100 page proposal sold in two working days pre-emptively to McClellend & Stewart.

(Struggling writers: feel free to be sad here.)

Writing about herself was “the only form of writing I had no interest in,” she says. “Writing in general seemed scary but writing about myself seemed terrifying.”

However, the resulting memoir, On the Outside Looking Indian, debuted as a bestseller on the Globe and Mail‘s book list, was picked up by Penguin Worldwide and was published by Riverhead Books in the U.S. in May 2012.

Even more importantly to her career, the rights to the novel were optioned by Toronto-based Amaze Film & Television in a deal co-agented by Toronto’s Jennifer Hollyer Agency. The option soon turned into a development deal with the CBC, a deal which remains in place today despite the struggles recently faced by the public broadcaster.

In the interm, while she was working on On The Outside, she’d met with Tim McAuliffe, who was running the CBC’s This Hour Has 22 Minutes. Following his suggestion to pitch 22 Minutes, she booked a multi-season gig with the series, honing her comedy writing chops for the screen in what she says was a supportive writing room (despite the competitiveness a show of that nature naturally engenders).

And more recently, she completed a stint on the first season of Halfire Entertainment’s Working the Engels.

What draws so many people to Gill’s work?

Hiyate says it’s simple: she tells universal stories with a unique twist, allowing people to both relate to and be intrigued by her. “She’s kind of like the Indian Nora Ephron,” he says. “She has that accessibility and universality.”

Although Gill will be the first to attribute the hand of lady luck in much of her success, she’ll also be quick to point out that without hard work – especially in the gruelling business of TV – all the opportunities in the world won’t make much of a difference in one’s career.

“Every time someone has found me, it’s because I’ve already done work and I’ve been willing to do whatever work they’ve needed from me,” she emphasizes. “It’s not like anyone has ever come my way and I’ve let them down. I am here to work.”

Her TV agent Illana Miller goes even further in her praise: “In the male dominated comedy industry, [Gill's] unique, fresh, female voice truly stands out, paving a way for diverse female writers in the boys club and destroying preconceived notions about female comedy writers.”

Gill is represented by Hiyate at The Rights Factory (literary), Miller at The Jennifer Hollyer Agency (TV, Canada) and Matt Solo and Melissa Myers at WME (TV literary, U.S.).

She is currently working on her second novel, a work memoir called Why Don’t You Get A Real Job?.

Correction: In the print version of this story, Playback incorrectly spelled Tim McAuliffe’s name wrong. Playback regrets the error. 

About The Author
Katie Bailey (@katie_bailey) is the editor and content director at Playback, overseeing the Playback brand as well as all content programs for the Banff World Media Festival. She likes dramas, thrillers, offbeat comedies, sci-fi, fantasy, how-to cooking, one renovation show and zero Kardashians.


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