Mathematical humor and insight are creative and pleasurable experiences. Both help students develop a positive attitude toward mathematics and facilitate higher-order thinking. The authors' classroom experience suggests that many middle school students have come to view mathematics as being a superficial and an uncreative activity where they learn procedures and solve predictable problems. At the same time, they have found that given the opportunity, students are eager to think mathematically at higher levels, to make connections and conjectures, and to extend investigations while posing their own questions. Mathematical humor may serve as a stepping-stone for students--and teachers--to attend deeply and creatively to mathematics and experience the pleasure of mathematical insight. (Contains 6 figures.)