A healthy vein of humor has infused jazz since its inception. Several writers have examined the topic of humor in jazz, but these studies have mostly covered the topic from cultural, anthropological, or other nonmusical viewpoints. While this is helpful scholarship, my study’s aim is to look more deeply at several recordings for the purpose of exploring jazz humor from a mostly musical perspective. I will discuss specific techniques that are employed by jazz instrumentalists, composers, and arrangers including mockery through musical means, the juxtaposition of styles, the overt use of technique, and deconstruction. The artists discussed in this chapter are Sonny Rollins, Charles Mingus, Plas Johnson, Oscar Peterson, Carla Bley, Joey Baron, and the Bad Plus.