This dissertation examines the ongoing influence of retro music cultures on post-1960s American artists and their representations of social, political, and economic change. Through a roughly decade-by-decade analysis of poetry, novels, film, and emerging technocultures, I make the case for a pendular dynamic of nostalgic art in the wake of the Civil Rights era—namely, a hope for revolutionary futures based on the past coupled with a backward-looking dirge for a Rubicon crossed, a moment of potential irretrievably lost. These twinned poles of optimism and pessimism share a nostalgic center in the music cultures of the past, emblematized in American art as agents of change and revolution, high water marks against which artists measure progressivism or cultural regression.