I examine how three major 19th-century philosophers – Mill, Schopenhauer, and Nietzsche – confronted the problem of pessimism: the worry that life might not be worth living. I demonstrate how all three took this problem to stem from concerns about the structure of human desires and interests, concerns Mill and Nietzsche both took specifically aesthetic value to play an essential role in answering. Taken together, these thinkers’ engagement with pessimism highlights two different aspects of aesthetic value’s importance to human well-being: human beings need to value things in an aesthetic manner, and they also need to view themselves as possessing a particularly aesthetic kind of dignity. In the absence of aesthetic valuing, human beings are unable to maintain non-aversive desires: that is, desires directed towards the good rather than merely away from the bad. In the absence of aesthetic dignity, the same aesthetic valuing needed to get our desires in shape would subject us to debilitating forms of self-contempt and self-disgust.