This week we are joined by Kevin McCaffrey! Kevin appeared on The Late Show with David Letterman, was a regular on truTV’s World’s Dumbest, VH1’s I Love the 2000s, and was a 2-time winner on truTV’s Comedy Knockout. He has 2 albums: “Nice & Drunk” (2018) and “Not Helping” (2024). He hosts two podcasts: “Sex and the Cidiots” and “The Bridgerton Bros,” with WGA award winner Jon Daly.

In this discussion, we explore growing up in Chicago, playing basketball, and an early passion for comedy and late-night television. Kevin shares his journey from childhood memories of Catholic school to his experiences in stand-up comedy and working at Late Night with David Letterman. He reflects on friendships formed through humor, the challenges of college life, and the excitement of moving to New York City. Kevin also discusses the unique experience of performing on cruise ships. Give this episode a listen!

Recommendations From This Episode:

Mark Twain Prize for American Humor: Conan O’Brien

Comedy Writing For Late Night TV

Follow Kevin McCaffrey: @kevinmccaff

Follow Carly: @carlyjmontag

Follow Emily: @thefunnywalsh

Follow the podcast: @aloneatlunchpod

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