Podcast Episodes
Back to SearchThe Citywide 50/50 Winner
Episode 797
Thanks to our audience and countless Albertans, we were able to give away the biggest jackpot ever with the Citywide 50/50. The final jackpot was a m…
11 months, 4 weeks ago
May 21, 2025 - Cuddling Adult Kids, Sesame Street Characters, and Dylan's Scammer War
Episode 796
Pepper tells the world his adult son still takes the time to cuddle his dad. Some of us find that strange. Is there an age where you should no longe…
1 year ago
Robbie's Stinky Fish Challenge
Episode 795
Robbie The Intern was forced to eat the smelliest food on the planet, Surströmming. He lost the latest Citywide 50/50 challenge to Pepper and this wa…
1 year ago
Pepper's Massive Victory Over Robbie
Episode 794
It was Pepper vs Robbie in the big battle to see who could help sell more Citywide 50/50 tickets. The loser has to eat the world's most rancid food, …
1 year ago
May 14, 2025 - Chicken Skin Debate, Getting Dumber, and The Punishment Reveal
Episode 793
Pepper throws away the skin of his rotisserie chickens and Dylan can't believe it. We need the audience's help to see if Pepper is considered blasphe…
1 year ago
The Citywide 50/50 Challenge: Pepper vs Robbie
Episode 792
Everything you need to know about the challenge Dylan has issued for Pepper and Robbie. It's all an attemept to help sell tickets with the surging Ci…
1 year ago
May 13, 2025 - Parking Ticket Predicament, Rogers Place Beers, and The Stinky Boyfriend
Episode 791
Pepper has another parking predicament. This time, he thinks his son is to blame for his ticket. Are Rogers Place beers the same as Rexall Place beer…
1 year ago
May 12, 2025 - Flower Shop Beef, Dylan's A&W Tab, and Mean McDavid?
Episode 790
Dylan has a beef with a local flower shop who tried to take advantage of him for Mother's Day. Pepper tries to make a top 5 list of the best leafy gr…
1 year ago
May 9, 2025 - Pepper's Inappropriate Comment, Robbie's Mother's Day Song, and Dylan's A&W Tab
Episode 789
Pepper starts the day with an inappropriate comment. Why Robbie can't claim to be a giant Oilers fan. We attempt to find out how big Dylan's tab was …
1 year ago
May 8, 2025 - Dylan Hit His Citywide 50/50 Goal!
Episode 788
We check in with Dylan after his second straight night of sleeping in the Devon A&W. We're always trying to learn new things on The Pepper & Dylan Sh…
1 year ago