Using research undertaken at the Olaf Stapledon archive at the University of Liverpool, this article explores the tension between cosmopolitan optimism and cosmic pessimism that structures Stapledon's 1937 novel Star Maker, and asks whether the novel succeeds in solving the philosophical problems that first spurred Stapledon to write it. I conclude, unhappily, that it does not: while an impressive achievement, and despite a surface optimism, the book's confrontation with infinity, totality, and the sublime is ultimately depressive rather than generative of a felicitous cosmological order, requiring Stapledon to try again and again to somehow solve this philosophical conundrum in the subsequent books that make up the later portion of his career.