For fifty years, the music, words, story, and fans of Bob Dylan have fascinated David Gaines. As a son, a husband, a father, a teacher, and a passionate lover of the literary in all its guises, he has pursued the poetic fusion of knowledge and emotion all his life. More often than not, Dylan’s lyrics and music have expressed that fusion for him, and so he has encouraged others to acknowledge the musician or writer or painter or director or actor or athlete who matters deeply (perhaps a bit mysteriously) to them, and to deploy that enigmatic passion in service of self-knowledge and social connection. After all, one of the central reasons to be a fan is to compare notes, explore mysteries, and riff with fellow fans in a community of exploration. Gaines’s personal journey toward creating such communities of passionate knowledge encompasses his own coming of age and marriages, fatherhood, and teaching. As a devoted fan who is also a professor of American literature, questions about teaching and learning are central to his experience. When asked, “Why Dylan?” he says, “He’s the writer I care about the most. He’s been the way into the best and longest running conversations I have ever had.” Talking with students, exchanging Dylan trivia with fellow fans, or cheering on fan-musicians doing Dylan covers during the Dylan Days festival, Gaines shows that, for many people, being a fan of popular culture couples serious critical and creative engagement with heartfelt commitment. Here, largely unheralded, the ideal of liberal education is realized every day.