Although some modern popular songs are deliberately composed for the purpose of commentary or protest, most are produced for commercial reasons. However, such songs may nonetheless be adopted by political, cultural, and social movements, and in these cases, fans’ participatory meaning-making has an important role in the songs’ new purpose. Taking the 1935 Korean ballad ‘Tears of Mokp’o’ as a representative example, this article traces how the melancholy love song acquired successive layers of meaning against the backdrop of changing politico-economic contexts throughout the twentieth century. Drawing on political, popular music, and sports histories, I first examine how ‘Tears of Mokp’o’ became known as an anti-colonial anthem under Japanese rule, a position that persisted in postwar South Korea. I then investigate the ways in which fans of the Haitai Tigers, a professional baseball team, utilized the song to express a complex set of emotions and commitments regarding their politically oppressed and economically neglected home region of Chŏlla. Against the backdrop of their traumatic memories of the 1980 Kwangju Uprising, Haitai fans, through their collective singing of ‘Tears of Mok’po’ in stadiums during games, transformed it from a colonial-era pop hit/anti-colonial anthem into a baseball fight song that expressed their spirit of regional insubordination in the 1980s and 1990s. Entering the twenty-first century, ‘Tears of Mok’po’ no longer played the same role for the Tigers and their fans, and it receded into historical memory. This change in meaning and association shows how the political and historical meaning-making of popular songs can be constructed, reintegrated, and even dismissed.