AI Can Make You Laugh. But Can It Ever Be Truly Humorous?
July 23, 2025

(Undark) – As people turn to AI for therapy and companionship, some say the models still need to learn the nuances of human humor.
Over his decades-long career as a late-night comedy TV writer, Joe Toplyn has crafted jokes for the likes of David Letterman and Jay Leno. He has instructed adult-level courses on comedy writing and taught hundreds of students how to script original comedy. And he has analyzed hundreds of jokes to understand their patterns and what makes them funny, and even wrote a book on the topic. So when generative AI came along, Toplyn wondered: Could he combine the linguistic skills of large language models, or LLMs, with the lessons he taught his human students to make a joke-writing machine?
The result was a wisecracking AI tool named Witscript — a web app where, for $5.99 a month, users can feed in prompts such as news headlines and image descriptions and get back jokes, funny captions, and other forms of clever wordplay. (Read More)