This chapter explores how humor and laughter can impact student learning and enhance the quality of educational encounters. I begin my analysis by outlining the historical marginalization of humor and laughter among Western philosophers while also briefly distinguishing between humor, laughter, and amusement. In the next part of this chapter, I examine the traditional conflict between education on the one hand and humor and laughter on the other. Following a brief historical survey, I turn to the insights that we can glean from contemporary research about the impact of instructional humor on student learning and on creating a positive classroom environment. To further illustrate the constructive role that humor and laughter can play in education, I present a number of concrete examples from different educational contexts. I conclude this chapter by offering some insights on the role that humor and laughter should play in education.