In this article, I analyze controversial humor and argue that the concept of disobedience is of central importance when evaluating, for instance, harsh or potentially hurtful jokes. Following social critic Erich Fromm (1900– 1980) I claim that disobedience is a dialectic concept: that is, it includes the possibilities both to affirm and to reject. This observation connects humor to other values, and pivotal is how humor is related to the question of what it means to be a human being. Through this insight, I argue that controversial humor may shock and be offensive, or it can be amusing and even have a cathartic effect. In the end, in evaluating humor it is necessary to analyze the values behind humor, that is, what humor obeys and what it disobeys.