Playwright, educator known as Joe From Winnipeg, Ian Ross dies at 57 By: Ben Waldman Posted: 2:21 PM CST Wednesday, Nov. 19, 2025 Last Modified: 5:32 PM CST Wednesday, Nov. 19, 2025 Updates

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Renowned Manitoban playwright, humorist and storyteller Ian Ross died suddenly on Tuesday at the age of 57.

Born in McCreary to a Saulteaux mother and Métis father, Ross — who was raised in the Métis community of Kinosota and in Winnipeg — took the theatre world by storm in 1997 when his first professional play, fareWel was awarded the Governor General’s Award for English Drama, making the 29-year-old Ross the first Indigenous person to receive the honour in Canadian history.

Ross began work on fareWel — a raw exploration of the financial realities of a fictional reserve called Partridge Crop — as a student in novelist Carol Shields’ creative writing class at the University of Manitoba, later developing his characters during group residencies at the Banff Playwrights Colony and at Toronto’s Canadian Stage.

“All of the writers in the group became fast friends and at our final session, we had a ‘silly’ gift exchange,” recalls playwright Dave Carley, who was then the editor of Winnipeg’s Scirocco Drama.

“With the enthusiastic approval of (Scirocco) owner Gordon Shillingford, I was honoured to give Ian a gift that was most definitely not silly — a publishing contract.

“It was the easiest decision we ever made. The play was tough and gentle, wise and very funny. Just like Ian,” recalls Carley of Ross’s debut work, which premièred in 1996 at Prairie Theatre Exchange.

Before graduating in 1990 with a degree in film and theatre studies from the University of Manitoba, Ross was on a pre-med track, but made the pivotal switch to the arts after meeting with a guidance counsellor.

Ross felt at home in the world of screen and stage, including his time with the student-run Black Hole Theatre Company, though he soon realized he would have to carve his own path if he had hopes for lasting success.

“I believe in using the ‘tickle technique’… You have to make audiences laugh. Hitting them with a bat is not the way to win them over.”

In 1997, after the fareWel hoopla, Ross, looking for steady creative work, contacted CBC Manitoba producer Tom Anniko to pitch a few concepts for radio segments.

Anniko liked one — commentary from an “average aboriginal man” — enough to book a recording session.

Ross wasn’t meant to be the voice on air, but on the first recording day, he told the Free Press in 2004, his friend no-showed, forcing the writer into the booth.

“I was freaking out, pacing back and forth. I looked at the script. We hadn’t even come up with a name.”

He asked the CBC technician at the board for his name, and the man said Joe Dudych; thus was born Ross’s everyman raconteur, Joe From Winnipeg.

For six years, Ross as Joe provided insightful, funny and cheeky weekly commentary on CBC Radio One on Thursday mornings, with its creator’s musings later compiled on CD and across three books, including the 2004 collection All My Best.

Ross didn’t stray far from theatre, finding a new calling as an educator with the collective Red Roots Theatre. One of his students in the early 2000s was Poplar Lake comedian-actor Paul Rabliauskas, who admired Ross’s commitment to infusing his work with pride in his Indigenous identity at a time when that wasn’t common in mainstream media.

“He turned out to be everything I’d hoped for. He inspired with such gentle grace and intelligence,” says Rabliauskas, who cast Ross in a recurring role on his CTV comedy series, Acting Good.

“The joy I got to see in his face when talking about story structure or punchlines — you could tell writing and creating were the things that kept him going.”

Ross’s output as a playwright was marked by a distinctive sense of humour, keen approach to displaying human imperfection and an overarching awareness of the power of the punchline to influence audience thinking when the narrative approached emotionally difficult terrain.

“He knew that pursuing a life in art, as a storyteller, was a journey and that all of us are on a journey to bring light to the world. His journey continues, and his legacy lives on in all who have been touched by him.”

“I believe in using the ‘tickle technique,’” he told the Free Press in 2009. “You have to make audiences laugh. Hitting them with a bat is not the way to win them over.”

Guided by that approach, Ross wrote plays including 1998’s Baloney! (about the child poverty crisis) and 2001’s The Illustrated History of the Anishinabe for Manitoba Theatre for Young People, where he served as the director of the Indigenous Theatre for Youth from 2013 on.

“If you spent any time with Ian, you could feel the joy he took in telling stories and sharing his thoughts. Often we’d be sitting in my office, dreaming something up, and inevitably Ian would take these beautiful detours to reveal something he had done, or thought or learned. It’s perhaps his stories that we will miss most,” says MTYP artistic director Pablo Felices-Luna.

Since 2020, Ross was the leader of the Royal Manitoba Theatre Centre’s Pimootayowin Creator’s Circle, a program aimed at nurturing emerging Indigenous artists to develop original plays. More than 20 artists have participated, with works by Rosanna Deerchild (The Secret to Good Tea) and David McLeod (Elevate: Manaaji’idiwin) making the jump from page to the John Hirsch Mainstage.

In March, Rhonda Apetagon’s In the Shadow Beyond the Pines — another Pimootayowin product — will première at the Tom Hendry Warehouse.

At this past September’s Pimootayowin Festival, where participants share their work in staged readings, Ross performed in his daughter Julia Ross’s comedy The Ojib-Way to Paradise as a velvet-voiced radio bingo caller.

“Ian chose the word Pimootayowin for the Creator’s Circle, as it means journey in Anishinaabemowin,” says RMTC artistic director Kelly Thornton.

“He knew that pursuing a life in art, as a storyteller, was a journey and that all of us are on a journey to bring light to the world. His journey continues, and his legacy lives on in all who have been touched by him.”

“Ian’s work was grounded in truth and wrapped in warmth and compassion, infused with his unique comedic voice,” says Ann Hodges, the artistic director of PTE, which produced fareWel, The Gap (2001) and The Third Colour (2019).

“We are not alone in grieving the loss of this remarkable and loved voice. Our condolences to his family, many friends and the countless lives he impacted.”

ben.waldman@freepress.mb.ca