This week on The Underground Lounge, Lou and Spank sit down with the legendary Deon Cole for a conversation that’s equal parts hilarious, insightful, and absolutely unpredictable. From the moment he steps into the Lounge, Deon brings that unmistakable Chicago energy and a lifetime of stories from the road, including his early days grinding in the Chicago comedy scene, rocking Timbs on stages that demanded suits, and literally changing the culture just by showing up as himself.

Deon opens up about discovering stand-up almost by accident, the moment he realized comedy was his purpose, and the unforgettable Def Jam tour experience that pushed him to level up his writing and craft. He breaks down how embracing silence became his comedic superpower, the origins of his iconic notebook on stage, and why he sometimes enjoys bombing on purpose just to keep audiences honest.

Lou and Spank dig into Deon’s wild journey from the clubs to becoming one of the most respected writers in the game, from helping craft Ricky Smiley’s classic prank call CDs, to joining Comic View, to eventually making history as the first Black writer on Late Night with Conan O’Brien. Deon shares behind-the-scenes stories from the writers’ room, how one unexpected bit turned into Emmy nominations, and the moment he almost quit the show before everything changed overnight.

The conversation goes even deeper as Deon talks about landing Angie Tribeca, becoming “Charlie” on Black-ish (a role originally written for Charlie Murphy), and navigating Hollywood in a way that’s stayed authentic to who he is. Along the way, the guys swap stories about clubs, cities, strip lounges, and why Chicago produces some of the funniest comedians in the world.

This episode is packed with gems for comedy fans, creators, and anyone who appreciates a raw, unfiltered look at the grind behind the glow-up. Deon’s honesty, humor, and perspective shine from start to finish, making this one of the most entertaining and inspiring sit-downs ever in the Underground Lounge.

Tune in now and enjoy the ride.