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.

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.

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.

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?

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.

When Jesse falls ill, Rhys steps in for a rare solo episode to issue a warning from lived experience. Drawing on his time in Wales during the 2016 Brexit referendum, Rhys explains how a seemingly fringe, “loonies and fruitcakes” movement blindsided the UK establishment, and what that means for rising Alberta separatism today.He connects the dots between economic inequality, media-fueled resentment, online misinformation, and the search for a charismatic leader, arguing that dismissing separatists as a joke is exactly how they can win. Rhys makes the case that the only real antidote is better governance: tackling affordability, opportunity, healthcare, and education so that Canada stays an awesome place to live and separatism remains on the fringe.

In this Patreon-only episode of Canada Is Boring, Rhys and Jesse dive into the truly biblical 1874–75 Rocky Mountain locust plague that turned the Prairies and parts of the US Midwest into a “living eclipse of the sun.” They tell the story of swarms estimated in the hundreds of billions to trillions of insects eating everything from crops and trees to wool, leather harnesses, and even the paint off wagons. We hear how desperate farmers tried burning locusts in straw, how carcasses polluted water and ruined livestock and eggs, and how aggressive plowing and an early frost helped drive the Rocky Mountain locust to extinction by the early 1900s.

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

In this part two of the Tim Hortons saga, Jesse Harley and Rhys Waters dig into how predatory private equity and corporate ownership have hollowed out one of Canada’s most beloved brands. Building on examples like Friendly’s and Toys “R” Us, they explain how firms use debt-loading, bankruptcy, and aggressive cost-cutting to squeeze short-term profit from companies, and how that model hit Tim Hortons after the Burger King/Restaurant Brands International takeover. They unpack franchisee lawsuits and alleged intimidation, the brand’s fall from a cozy community hub to a transactional, depressing pit stop, and how centralized supply chains, shrinkflation, staff cuts, and PR spin eroded both quality and reputation. The conversation widens to the Temporary Foreign Worker Program, corporate lobbying, and how bad policy and labor exploitation help fuel public anger about immigration and housing pressure, before circling back to a simple call to action: skip the hollowed-out chains when you can, and support local independent coffee shops instead.