This essay explores white masculinity and the recuperation of privilege in the figure of Sturgill Simpson, an American country music singer from Jackson, Kentucky. Operating at the intersection of country music studies and third wave whiteness studies, it demonstrates how Simpson deploys the outsider identity of the industry outlaw to recuperate insider benefits of critical acclaim, commercial success, and creative license. As an artist who makes country music for “people who don't like country music,” Simpson functions as a representative figure of the adaptive tactics of white masculinity and the broader politics of inclusion and exclusion in contemporary country music.

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