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This dissertation is about the moral importance of irony. In the first chapter, I introduce the topic. I argue that having values makes us vulnerable to facing choice situations that we properly regard as absurd, and I articulate a form of ironic playacting as an apt response to those choice situations. The subsequent chapters draw out the implications of this account. The second chapter treats akrasia. I defend the virtues of an overlooked kind of self-awareness in akrasia. In doing so, I articulate the importance of taking oneself seriously in a way that will make akrasia apt to seem absurd and to call for ironic playacting. In the third chapter, I argue that contentment and affirmation play a wide-ranging role in our practical thinking, in light of their ubiquitous connection to what we value, and this makes us apt to encounter absurd choice situations that call for irony. In the fourth chapter, I consider a common but puzzling phenomenon: the way in which the thought that some emotion is “not worth it” shows the emotion not to be fitting. My explanation of this phenomenon shows how we can end up in emotionally absurd situations that call for ironic playacting.