The New York–based comic Adrienne Iapalucci has a joke that I simply cannot stop thinking about. It goes like this: ‘My boyfriend told me he was going to kill himself and I was like: “Great, now I won’t be able to kill myself or people will think we were in love”’. This short and somewhat cynical joke may be a reflection of a deeply disturbed and fundamentally warped mind; to many listeners, it should and probably will raise serious concerns about the joke writer’s overall mental health. And, yet, even after having examined this and many other similar troubling jokes written by Iapalucci numerous times, I continue to find it to be one of the funniest and most perplexing jokes I have ever heard. As a piece of comedic craftsmanship, it is extremely well made: It is economic in the use of words; there is a startling but appropriate incongruity between set-up and punchline; and the payoff—the humorous experience—comes in waves. First there is the surprise that arises from the immediate appreciation of the contradiction between set-up and punchline, and then the deeper and more puzzling realization of what the implications of the joke might actually be. And all of this is predicated, of course, on the assumption that the listener finds the joke funny to begin with.