Kim Dong-ri and Seo Jeong-ju were prodigious personalities of Korean literature in the 20th century. The friendship of these prominent writers began in the 1930s and lasted their entire lives. Together they contributed to the reconstruction of the literary world in Korea after the end of the Japanese Occupation. This paper examines their biographies, auto-biographies, and different testimonies in an attempt to understand and appreciate not only the development and depth of their friendship, but also their legacy to Korean literature that was based on the literary and humanistic values they shared.