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Jamie Jackson sits down with renowned roast battle icon Tyler Morrison to talk all things comedy & Canada’s entertainment landscape: what it really takes to chase a dream, put yourself out there, & make people laugh.

The conversation dives into economic & cultural obstacles for Canadian artists, riffing on Luc Rinaldi’s Walrus article with Skye Wallace: 📰 "The Death of the Middle-Class Musician".

Canadian musicians are squeezed by low streaming revenue, touring costs, & a lack of sustainable support, threatening the very survival of full-time artistry: What kind of country do we want for our creatives? What happens when the middle class in music, and in comedy, disappears?

They touch on rising costs in sports, local media, polarization, & the rise of politically incorrect comedy while keeping laughs rolling, packed with anecdotes & moments of reflection. Whether a die-hard comedy fan, an up-and-comer or just wondering what happened to your rock ‘n’ roll dreams—this is for you. 🎸🎧

Reach Tyler @tylermorrison123 OR https://cottagecomedy.com/

⏱️ Chapters

00:00—Tyler Morrison & the Comedy Scene
05:59—Substance Use, Community, & Rural Realities
11:43—Polarization
17:23—Challenges for Artists
19:30—Entertainment in 2025
22:40—Streaming Services/Modern Cinema
24:27—Music Streaming & the Artist’s Raw Deal
26:42—Songwriting & Authenticity in Art
28:25—Cost of Sports
32:27—Decline of Local Media
34:24—Accountability & Cancel Culture
38:21—Comedy: Then & Now
40:21—Changing Reception of Jokes: Rise of Politically Incorrect Comedy
52:24—Russell Peters: Viral
55:46—The Comedy Boom: Canadian Frustration
58:22—Comedy after COVID
01:01:30—Local Support & Word-of-Mouth
01:08:40—Canadian Artistry
01:09:53—Social Media & Promotion
01:16:54—Stories in an Age of Noise
01:21:23—Identity, Humour & Canadian Culture
01:22:43—The Tragically Hip
01:27:05—Roasting, Respect, & the Knife’s Edge
01:37:16—Advice for Aspiring Comedians & Writing Jokes
01:46:56—Digital Comedy: Changing Stages & Power
01:54:50—The Future

Keywords

stand-up, comedy, roasts, social media, Tyler Morrison, John Moses, Tom O'Donnell, Cottage Comedy, Main Offenders, Fight Stories, Scott Thompson, Just For Laughs, Yuk Yuks, Big Wreck, Skye Wallace, Canadian Music, Mark Gagnon, Ron Josol, Andrew Schulz, polarization,

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Remember, my friends: We're in this thing together. It means more than you know. We're just getting started!

If you know of anyone-- or if YOU have an amazing story of grit, or even something to share with the world, why not reach out and let me know?

I'd love to give voice to your stories.

All the very best.

Your good pal,

-Jamie