This thesis explores the clown paintings of Jack Butler Yeats with particular emphasis on those painted between 1920 and 1950. Yeats was interested in circus performances from a very young age. In general, his clown paintings seem to capture traditionally showy and exuberant images of both clown and circus. However, they also reveal Yeats' personal sense of the painter as clown. Laughter (who laughs, the permanent grimace) and the symbolism of the rose are significant in establishing the artist as a clown figure. Moreover, the idea of the clown also spoke to the arrival of the modern era. The balancing circus performer and the grotesque are particularly important to Yeats' use of comedy and tragedy. This thesis examines Yeats' clown paintings for their personal, cultural, and global significance. It attempts to situate the works with Yeats' own writings as well as a greater academic circle, including the works of Charles Baudelaire, Friedrich Nietzsche, Samuel Beckett and W.B. Yeats. Finally, it looks to relate the clown paintings to the greater political scene in Ireland and abroad.