Deon Cole joins Jim to discuss how the entertainment industry has evolved over his career in Hollywood. Cole talks about what it takes to learn comedy writing, how he became a writer The Tonight Show with Conan O'Brien, and reveals how one elevator ride led to Andy Richter becoming Conan's sidekick. Cole also discusses how the emergence of AI can affect the entertainment industry, his evolution from comedian and writer into actor with screen credits in "Black-ish" and the "Barbershop" movies. Cole also reveals his best comedian icons of all-time, and why filming his 2022 Netflix stand-up special "Charleen's Boy" was such a poignant experience.

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