Admittedly T. S. Eliot’s “Rhapsody on a Windy Night” was primarily inspired by Henri Bergson``s Matter and Memory. Unlike this argument, however, this paper aims to review this poem not only centering upon Matter and Memory, but also embracing his other major philosophical works, Time and Free Will, Creative Evolution, and Laughter. In the light of the fact that Eliot took Bergson’s lectures on his major philosophical works in College de France, I believe that Matter and Memory alone does not fully account for the whole meaning of this poem. This paper thus delves into how Eliot projected Bergsonism into the contrast between inauthenticity of anonymous people and authenticity of individuals pursuing an artistic life in pure duration, and thereby how he questioned the dilemma of modern men intertwined with the conflict between body and spirit and between matter and memory in the contemporary society. Pitting an automatic, responsive, and imitative life against an original, artistic, and creative life, Eliot reveals his deep despair toward the spiritless life of modern men who do not know the real value of freedom.