The work of American musician and songwriter Bob Dylan is an intriguing theme of research for the social psychology of music because his songs are widely believed to have reflected and influenced social movements. The objective of this mixed-methods study was to analyze the content of Dylan’s song lyrics from his 29 original studio albums (1962–2012), selecting only songs written by him (n = 241) in order to determine whether and how they evolved over the course of 50 years of his career. First, the text analysis software Linguistic Inquiry and Word Count (LIWC2007; Pennebaker, Booth, & Francis, 2007) was used to perform a quantitative analysis of song lyrics. Second, a general inductive method was used to perform a qualitative analysis of Dylan’s work. Quantitative results showed that the most pronounced changes in Dylan’s lyrics throughout his career included an increase in words indicative of cognitive complexity, religious content, and collective focus, but also a decrease in words indicative of social referents. Qualitative analysis revealed that Dylan’s song lyrics gravitated around social themes that primarily consisted of hardships, romance, religion, family, politics and law, as well as oppression. Findings are discussed within Dylan’s musical work and biography, and provide theoretical and empirical directions for future research.