This research examines the musical preferences, listening habits, and values of individuals who listen to a musical subgenre known as alternative country music (“alt-country”). Using a fine-tuned qualitative approach, I conducted 20 semi-structured, in-depth interviews with alt-country listeners located across the country to understand how fans conceptualize their musical affinities within the context of a highly polarizing and stigmatized music genre. I find that alternative country listeners engage in a unique set of musical practices that distinguish themselves from other actors in the musical field. Respondents participate in discourses of authenticity—personal, artistic, and regional—to legitimize alternative country music in terms of its artistic value, casting the subgenre as the most genuine successor to the country music tradition. In the process, listeners forge associations between musical genres and social categories that reinforce symbolic boundaries between classes of country music fans as well as others who are “really into music.” Crucially, I find structured variations in how listeners make political and regional assignments to the subgenre, reflecting a desire to frame musical affinities within the context of one’s own identity and experience. Situating these findings within scholarship on taste development and cultural legitimacy, I suggest that certain alt-country listeners may be considered both dominant over and marginalized by country music. The legitimating strategies adopted by these individuals simultaneously reflect processes of symbolic differentiation, exclusion, and resistance through music.