James Thurber, along with others who wrote for The New Yorker magazine, developed the 'little man' comic figure. The little man as a central character was a shift from earlier nineteenth-century traditions in humor. This twentieth-century protagonist was a comic antihero whose function was to create sympathy rather than scorn and bring into question the values and behaviors of society rather than affirm them, as earlier comic figures did. The little man was urban, inept, frustrated, childlike, suspicious, and stubborn. His female counterpart was often a foil: confident and controlling enough to highlight his most pitiable and funniest features. Contradictory gender roles and stereotypes are essential to Thurber's humor. This thesis thus reads Thurber's work as critical of gender roles. Thurber's humor demonstrates that expectations for men and women to be socially masculine and feminine are often incongruous with their capabilities and natures. Often his work is funny because of the way it portrays gender as performance and as expectations imposed upon people instead of as inherent qualities in men and women. These roles create conflicted characters as well as conflict between the characters that Thurber draws in his stories, often a quarreling husband and wife. Also characteristic in Thurber's humor is the element of neurosis. Thurber often played with the vernacular concepts of neurosis, and he capitalized on public obsession with Freudian psychology with his satires and with fiction and essays about various anxieties and daydreaming. Neurosis works well as comic material because it also catalyzes the battle of the sexes. To support my interpretation of Thurber as a critic of societal gender roles, Freud's book The Joke and Its Relation to the Unconscious is useful at illuminating a deeper 'tendency' in Thurber's humor. Thurber is often thought of as a misogynist, for his personal behavior and for his unflattering literary portrayal of women as unimaginative nags. This thesis also examines the complexities and developments of Thurber's attitudes toward women. Most importantly for Thurber, his little man figure and the battle of the sexes was a way to express the importance and power of the liberated human imagination.