Masculinities have been rearranged in rural communities across the United States over the last four decades in response to shifting socioeconomic conditions. However, whether and how rural masculinity has been redefined at the national level over this same time period has received less attention. This paper presents a longitudinal analysis of representations of masculinity in mainstream country music from the 1980s to the 2010s. Analyzing the lyrics from over 800 weeks of songs that topped the Billboard country music charts, I find that working‐class occupations and heterosexuality were relatively consistent components of representations of men across these decades. There were also two notable transformations. Depictions of providing shifted away from a traditional breadwinner toward men providing women with alcohol, transportation, and places to hook up. Masculinity and whiteness also became more closely linked. I argue that these rearranged intersections of gender, class, sexuality, and race enable the continued reproduction of gendered inequalities amid rural men’s worsening employment prospects. These results suggest shifting intersections of gender, class, sexuality, and race will inform how gendered inequalities are reproduced as socioeconomic conditions continue to transform in rural communities.