This essay explores how gender is constructed through the lyrics of Bob Dylan, across three time periods of his career. Using a mixed-methods approach that combines quantitative analysis with close readings, and thematic interpretation, the study focuses on representations of masculinity, femininity, and power dynamics. Drawing theoretical support from Judith Butler’s theory on gender performativity, Norman Fairclough’s Critical Discourse Analysis, and Deborah Cameron’s critique on gendered language myths, the study examines Dylan’s characters’ shifts over time, from one-dimensional and flat, to multifaceted and complex, all through the eyes of a male narrator. Relational themes such as desire and control - central to this paper - are likely to remain relevant decades from now, and the same can be said for Dylan’s body of work.