Can AI Be Funny? With ComedyBytes’ Eric Doyle Artwork

AI-Curious with Jeff Wilser

A podcast that explores the good, the bad, and the creepy of artificial intelligence. Weekly longform conversations with key players in the space, ranging from CEOs to artists to philosophers. Exploring the role of AI in film, health care, business, law, therapy, politics, and everything from religion to war.

Featured by Inc. Magazine as one of "4 Ways to Get AI Savvy in 2024," as "Host Jeff Wilser [gives] you a more holistic understanding of AI--such as the moral implications of using it--and his conversations might even spark novel ideas for how you can best use AI in your business."

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AI-Curious with Jeff Wilser

Can AI Be Funny? With ComedyBytes’ Eric Doyle

August 14, 2025 • Jeff Wilser • Season 1 • Episode 103

Can artificial intelligence actually be funny, or is humor still a human stronghold? We explore that question with Eric Doyle, co-founder of ComedyBytes, a Brooklyn-based multimedia comedy show where AI and humans face off in roast battles, dating games, and other interactive formats. Doyle combines the craft of stand-up with the tools of generative AI, building AI characters like “AI Kanye West” or “AI Sarah Silverman” that deliver pre-scripted jokes in real time.

In this episode of AI-Curious, we dig into:

[0:52] The story behind ComedyBytes and its AI-powered format
[3:46] How AI roast battles work, from concept to stage mechanics
[7:53] Using tools like ChatGPT, Claude Sonnet, and Gemini AI to write jokes
[12:55] The art of prompting for humor and boosting the “funny hit rate”
[16:36] Why specificity matters in generative AI comedy
[23:43] Inside the “Data-ing Game,” an AI twist on the classic dating game
[25:58] Can AI really be funny—or just imitate the structure of humor?
[32:30] The triple, listing technique, and other joke-writing structures AI can learn
[39:10] Advice for non-comedians using AI to add humor
[41:24] The future of AI in entertainment and its impact on creators

From the structure and anatomy of a joke to the ethics of deepfake comedy, this conversation blends technology, performance, and the evolving role of AI in creative work. Whether you’re an AI enthusiast, a comedy fan, or simply curious about where these worlds collide, this is a look at AI and humor you haven’t heard before.