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May 15, 2025 46 mins

Why does comedy work in audio ads—and why don’t more brands take the leap?

In Season 3 Episode 6 of Ad Infinitum, Stew Redwine is joined by improv legends Wayne Brady and Jonathan Mangum, co-hosts of Wayne Brady's What If?! with Jonathan Mangum, to explore the strategic (and often hilarious) role of humor in audio advertising. They unpack the data, riff on Stew's obsession with the comedic potential for life insurance ads, improvise jingles, and roast real radio spots from recent top spenders Progressive, Home Depot, Discover, and ZipRecruiter. Along the way, they reveal how brands can break out of the safety zone, find their comedic voice, and stand out in an AI-driven sea of sameness.

Special thanks to Headgum for hosting Ad Infinitum at their studio for this episode!

Support the show

Ad Infinitum is Presented by Oxford Road and Produced by Caitlyn Spring & Ezra Fox, MFA, written & hosted by Stew Redwine, and sound designed by John Mattaliano, with audio production by Zach Hahn.


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