Game audio designers increasingly turn to folk musicians for expertise as recording artists and consultants on compositional styles. These practitioners help ground video games in cultural traditions and provide a sense of musical authenticity. Yet any attempt at depicting authentic “American” music brings with it a crisis of identity. This chapter examines the challenges of authenticity and identity in American music within games through two key inquiries: (1) how romanticized depictions of the American West and its past complicates any notion of what we can deem to be authentic, and (2) how common ideas in American country, Western, and folk music reinforce themes of isolation, despair, and loneliness in player and character identities. The primary case study is the narrative-driven game Where the Water Tastes Like Wine. Composer Ryan Ike collaborated with musicians across the United States who added personal nuances to create what was described as an authentic Depression-era sound (Thomas Quillfeldt, 2018). By analyzing this game’s themes of wandering and poverty alongside concepts of authenticity, I examine the hybridity and “multiplicity of authenticity” in Ike’s music. Although I look specifically at certain types of American music in Where the Water Tastes Like Wine, I also consider broader identity formations through American music in other games that center on rural United States and the American West. This further demonstrates how players can emotionally connect with negative valences of video game characters, through a ludic joy of despair.