The Sexiest Man in Winnipeg

The Sexiest Man in Winnipeg

In this episode of Canada Is Boring, Rhys and Jesse dive into the bizarre true story behind Amazon Prime’s The Sexiest Man in Winnipeg, following former Winnipeg TV news anchor Steve Vogelsang from 1990s local celebrity and “sexiest man” titleholder to financially ruined, depressed journalism instructor living in his truck and ultimately turning to a hilariously low‑yield bank robbery spree across Regina, Saskatoon, and Medicine Hat. They unpack his “plan” to rob 25 banks for a few thousand dollars at a time using fake bombs and a glue gun, the legal quirks of what counts as armed robbery in Canada, how he was eventually caught after his truck broke down near the scene, his 6.5‑year prison term, and his attempt to rebrand himself as a men’s mental health advocate

For premium content, socials, merch, to leave a voicemail or message us go to canadaisboring.com

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The Psychic Scam King

The Psychic Scam King

In this episode of Canada Is Boring, Rhys and Jesse dive into the bizarre, lucrative world of psychic mail-order scams led by one of Canada’s most successful fraudsters, Patrice Runner.Starting with h...

1 Kesä 40min

CSIS, Oil, and the Pipeline Protestors (Premium)

CSIS, Oil, and the Pipeline Protestors (Premium)

In this special friends–only episode of Canada Is Boring, Rhys and Jesse dig into the story of how CSIS, Canada’s spy agency, allegedly spied on Indigenous and environmental activists protesting the E...

25 Touko 4min

Bear-Proof Dreams: The Legend of Troy Hurtubise

Bear-Proof Dreams: The Legend of Troy Hurtubise

Rhys and Jesse dive into the legendary Canadian documentary Project Grizzly and the life of its unforgettable star, Troy Hurtubise—the man who spent years and thousands of dollars building bear-proof ...

18 Touko 46min

Red Ryan: Canada’s Fake Reformed Gangster

Red Ryan: Canada’s Fake Reformed Gangster

Rhys and Jesse dive into the wild life of Red Ryan, a Toronto-born hooligan who grew into one of Canada’s most notorious early 20th‑century criminals. From leading street gangs at 10, to hard labor in...

11 Touko 37min

Our 2026 Show Trailer

Our 2026 Show Trailer

Hosted by Rhys, a new Canadian with an outsider’s obsession for the country’s strangest stories, and Jesse, a proudly disengaged average Canadian, the show digs into the weirdest moments in Canadian h...

6 Touko 30s

From Olympic Snowboarder to Cartel Kingpin

From Olympic Snowboarder to Cartel Kingpin

A Canadian Olympic hopeful walks away from the slopes and into the heart of a violent international drug cartel. Rhys and Jesse trace Ryan James Wedlake’s path from Thunder Bay ski kid to Sinaloa lieu...

4 Touko 38min

Toronto's Mystery Tunneller

Toronto's Mystery Tunneller

Rhys and Jesse dig into the bizarre true story of Toronto’s 2015 “mystery tunnel” near York University. What started as a three‑metre‑deep, hand‑dug hideout with plywood supports, a generator, rosary ...

27 Huhti 38min

Toronto's Dead Raccoon Vigil

Toronto's Dead Raccoon Vigil

Rhys and Jesse return to with one of the most delightfully absurd Canadian stories ever told: the 2015 Yonge Street dead raccoon memorial. What begins as a sad little scene on a Toronto sidewalk turns...

20 Huhti 37min

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