Jokes from a Humorless Machine: A Comedic Romp through Artificial Intelligence explores whether AI, specifically ChatGPT, has enough of a sense of humor to create jokes that will tickle the funny bone of contemporary Americans. Through a series of prompts, the authors ask ChatGPT to develop jokes on classic themes as well as contemporary issues with surprising results, all demonstrating AI's sense of humor as shaped by its algorithmic woke sensibilities. Preston Lewis, an award-winning humorist, and Harriet Kocher Lewis, his award-winning editor, challenge ChatGPT to humor them with a series of prompts to develop jokes on classic themes like knock-knock, yo mama, three fellows enter a bar and the reason the chicken crossed the road. Then the authors move on to more contemporary issues like politics, politicians and gender identify, challenging ChatGPT to find humor in modern culture. Finally, the authors seek from ChatGPT observations on contemporary culture in the style of several American humorists and more recent comedians. In the process, the authors not only touch on the history of classic comedic memes but also discover biases in the resulting AI output. Are the jokes sensitive? Absolutely! Are they politically correct? Without a doubt! Are the jokes funny? The reader will decide. Jokes from a Humorless Machine is the second book in the authors' Magic Machine Series. Their surprising initial offering on artificial intelligence-Devotionals from a Soulless Machine-provided a sensitive look at ChatGPT's take on the Bible.