Why We're Teaching Machines to Be Funny While Forgetting How to Laugh at Ourselves

My grandmother once told a joke so bad that my cousin, then six, looked up from his mashed potatoes and said, "Grandma, that was not a joke. That was a sentence." He was right. He was also, arguably, doing what most large language models still cannot: distinguishing a joke from a sentence that merely resembles one.I've been thinking about this a lot, mostly because we are now several years into the era of asking machines to be funny on purpose, and the results have been, how do I put this charitably, a sentence.The Stoic Machines Have Entered the Open MicHere is the situation as best I can describe it without making my editor cry. AI has slid into nearly every chamber of daily life. It writes our emails, sorts our groceries, recommends the songs we pretend not to cry to. It is, by most measures, competent. What it is not, and what it desperately wants to be, is charming.In 2023, researchers at Cornell University used hundreds of New Yorker Cartoon Caption Contest entries as a testbed…