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.

00:00 – Cold open: “What the fuck are we talking about this week?”
00:14 – Canada’s many Ryans & introducing “Red Ryan”
00:50 – Canada is boring? Montage & comedy cold open
01:50 – Show intro: “Canada Is Boring” + NPC joke
02:10 – Red Ryan’s early life as a hooligan (Toronto, 1905)
03:30 – First serious crimes & hard labor at Kingston Penitentiary
04:50 – Released, first armed robbery at 19 & love of guns
05:50 – World War I: prison-to-soldier deal and desertion in England
06:40 – Robberies in England & return to Canada after the war
07:10 – Marriage, abandonment in Winnipeg & bank jobs to Montreal
07:50 – 25-year sentence for armed robbery & maiming charges
08:20 – “Most daring” Kingston prison break (Hemingway mention)
09:20 – Bank robberies across the U.S. Midwest & high life
10:10 – Capture in Minneapolis & life sentence back at Kingston
10:50 – The 9-year “model prisoner” scam begins
11:10 – Writing The Futility of Crime & befriending Father Kingsley
12:00 – Prison riot, politics & using reform to angle for release
13:00 – Government visit to Kingston & showcasing a “reformed” Ryan
13:35 – 1935: Life sentence canceled, Ryan released after 11 years
13:55 – Media celebrity: “Canada’s Dillinger,” radio show & VIP events
14:40 – Suspicious “long car trips” & being paid just to sit in a hotel lobby
15:10 – How he could have gone straight (Jesse’s reflection)
15:25 – Lectures, weekly chaplain visits & keeping up the act
16:10 – Ad break: “Canada is boring dot com” & Patreon/speakpipe plug
17:48 – Anonymous letter: allegations of bank robberies & women
18:10 – Ryan gaslights the priest & keeps robbing in secret
18:30 – Still robbing banks while famous – masked robber speculation
18:58 – 1936 escalation: killing a man & wounding his son
19:40 – Victoria Day: setting up the liquor store #46 robbery in Sarnia
20:50 – The 25-cent short customer & discovering the masked bandits
22:10 – Store locked, bystanders notice & alert a taxi stand
23:00 – Police arrive: tension builds inside liquor store #46
24:00 – Gunfight erupts: police vs. Red Ryan & his partner
24:45 – Officer killed, Ryan and accomplice shot dead
25:30 – Public shock: “The reformed celebrity was still a criminal?”
25:55 – Bodies displayed to the public & 6,000 people viewing
26:35 – Hero’s funeral for the slain officer
27:00 – Jesse’s moral verdict: cool story, awful murders
27:50 – Crime from desperation vs crime for fun (Jesse’s rant)
29:15 – Wrapping up the Red Ryan story & Jesse’s frustration
29:35 – Transition: “Shall we dip our toes into the STD zone?”
30:07 – STD Zone stinger: entering the Small Talk Dimension
30:32 – Small talk: Jesse introduces the powdered-wig dinner party
30:49 – 1745 costume fitting & playing a Scottish noble
31:30 – Learning a Scottish accent & full period dinner immersion
32:15 – Jacobites vs loyalists: Bonnie Prince Charlie homework
33:40 – Playing out political intrigue at the party
34:30 – The parchment trade agreement & the “X” signature incident
35:50 – Misunderstanding resolved: “I’m illiterate, not insulting you”
36:15 – Everyone secretly pantsless (joke) & wrapping the anecdote
36:24 – Show wrap-up: website, Patreon, bonus episodes & speakpipe
36:57 – Final goodbyes
37:06 – Outro song: “Canada is boring” theme