Addressing how Dolly Parton’s Netflix anthology series uses transmedia storytelling to reimagine her earlier music, I argue that it revises narratives about country music history. As Parton reframes songs like “Jolene,” her work underscores how her gender performance challenges gender stereotypes in country music performance history. By turning songs into television stories, Parton adapts to recent trends in transmedia storytelling. Her autobiographical authenticity narratives make her especially well-suited to new media self-branding. As critics such as Nadine Hubbs, Francesca Royster, Diane Pecknold, Kris McCusker, and Jada Watson have argued, we must continue to account for more nuanced readings of gender in country music history, particularly as it intersects with race, class, and sexuality. I demonstrate how Parton’s series speaks to the variety of gender expression and gender critiques in a range of country performances. I also call for more discussion of transmedia storytelling, intertextuality, and affect studies in the field.