It is a matter of common knowledge that and shared a common worldview. Everyone familiar with the works of these two thinkers should recognize their general philosophical affinities. Both men were pessimistic about the power of human reason and attributed human behavior to powerful unconscious forces and, as a result, both were deeply skeptical about the future of human society. Drawing from previous literature, this essay compares the philosophical theory of Schopenhauer with the psychoanalytic theory of Freud. We find that, while Schopenhauer and Freud share a common philosophical orientation and diagnosed the same fundamental problems with life in civilization, they proposed some ostensibly similar, yet ultimately very different solutions. Focusing on each thinker's respective notion of sadism and masochism, this paper tries to understand and come to terms with the dimensions of this radical pessimism.