Canada is Boring

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 Kingston Penitentiary, to a wartime desertion and a “most daring” prison break that even inspired Ernest Hemingway, Ryan’s story is packed with chaos.

They unpack how Ryan pulled off a decade‑long scam as a “reformed” model prisoner—writing a book, sculpting Virgin Mary statues, charming a prison chaplain, and emerging as a media darling with his own radio show—while secretly robbing banks on the side. It all ends in a bloody liquor store shootout in Sarnia that shocks a country that thought it had found its redemption poster boy.

Plus, in the STD (Small Talk Dimension) zone, Jesse recounts a ridiculously elaborate 1745 powdered‑wig dinner party, complete with questionable Scottish accents, Jacobite plotting, and a near “diplomatic incident” over a misunderstood signature.
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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 history, politics, crime, culture, and folklore. From mystery tunnels and dead raccoon vigils to government “gaydar” machines, border brawls, Olympic snowboarders turned cartel figures, and the time the U.S. Army gassed Winnipeg, Canada Is Boring turns the overlooked, absurd, and unbelievable corners of Canadian life into addictive, hilarious storytelling.

Part history show, part comedy podcast, part national identity crisis, Canada Is Boring is for anyone who likes their learning with jokes, their politics with chaos, and their Canadian facts deeply, deeply strange. The show has built a loyal audience by making Canadian stories feel surprising, accessible, and genuinely entertaining, earning recognition as Canada’s No. 1 Politics Podcast on Goodpods, breaking into the Top 5 Podcasts in Canada on Apple Podcasts, hitting No. 1 Trending on Spotify Canada, and reaching No. 3 in Canada for Comedy.

Whether you’re Canadian, new to Canada, Canadian-curious, or just looking for weird stories to annoy your loved ones with, Canada Is Boring offers a hilarious weekly reminder that this country is not dull. It is bizarre, dramatic, petty, dark, ridiculous, and occasionally on fire.

Canada is boring? Nope. Canada is unhinged.
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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 lieutenant, weaving together family privilege, failed glory at Salt Lake City, cannabis grow ops, Hawala money transfers, and FBI most‑wanted status—plus an eventual takedown that netted tonnes of cocaine and millions in assets.
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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 beads, and a poppy quickly spiraled into global speculation: terrorist bunker for the Pan Am Games? Gang weapons cache? Something far worse?
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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 into a full-blown public vigil—complete with Post-it notes, roses, sympathy cards, candles, a Jesus candle, a collection box, and even a parody Twitter account. It’s internet weirdness, and heartfelt stupidity all rolled into one episode.
For premium content, socials, merch, to leave a voicemail or message us go to canadaisboring.com
Hosted on Acast. See acast.com/privacy for more information.