Pessimism has a strange status in Western culture. Often overly morose, antagonistic, and resigned to failure, pessimism is at once a philosophical position and yet it is frequently dismissed as simply a ‘bad attitude.’ Indeed, some of the great pessimist philosophers (most notably, Schopenhauer) also excelled at being curmudgeonly and generally grumpy. Other pessimists (such as Nietzsche) argue that pessimism, when pushed far enough, must become a kind of optimism. As a philosophy, pessimism is also characterized by its stylistic quirks – pessimist writings most often eschew systematic philosophy in favor of the aphorism, the fragment, the observation, even prose poetry. Indeed, many works in the pessimistic vein straddle the space between philosophy and literature. This seminar will engage with key works in the pessimist tradition, noting pessimism’s always-tenuous relation to philosophy. Works by the following may be included: Albert Camus, E.M. Cioran, Franz Kafka, Giacomo Leopardi, George Friedrich Lichtenberg, Thomas Ligotti, Friedrich Nietzsche, Keiji Nishitani, Blaise Pascal, Fernando Pessoa, Arthur Schopenhauer, Lev Shestov.