Schopenhauer argues, strikingly, that it would have been better if life had not come into existence. In this essay I consider this pessimistic judgment from a philosophical perspective. I take on the following three tasks. First, I consider whether such judgments, apparently products of temperament rather than reason, can be the subject of productive philosophical analysis. I argue that they can be, since, importantly, we can separate arguments for such judgments that establish them as plausible from those that do not. Second, I evaluate Schopenhauer’s arguments for pessimism. I argue that although we must reject Schopenhauer’s main argument for pessimism, he has another, more plausible argument for pessimism that hitherto has been neglected by scholars. Finally, I argue that although pessimism can be established as the correct judgment about life in some possible worlds, in our world the question of pessimism or optimism cannot be definitively answered.