Pete Seeger and Woody Guthrie, two legendary figures of American folk music, lived through some of the most tumultuous periods of the history of the United States. The circumstances they grew up in and the people they encountered led them to meet communism in the 1930s. Being two independent souls, they were not registered members of the Communist Party but walked on the same path for years as “fellow travelers.” Both men claimed that they wrote and sang songs for the causes they believed in without being subjects of a larger organization. However, an analysis on their political views from the late 1930s to the early 1940s, particularly their change of political stance in the aftermath of the German invasion of the Soviet Union in June 1941, indicates that their political mindset was in close resemblance with the stance of the Communist Party. This thesis narrates the story of how Pete Seeger and Woody Guthrie became firm supporters of the United States’ entrance into World War II with all their war songs in a matter of months even though they previously displayed a strict anti-war stance with many songs manifesting their standpoint, and how this change was in near-perfect alignment with that of the Communist Party.