Sheffield recounts his first encounter with Taylor Swift’s music. In 2007, he stumbled upon “Our Song” at home when the CW played it between episodes of the television show he was watching. He writes that he was immediately enraptured by the song’s lyricism, and hoped at the time that Swift’s career would produce “another great song or two” (xiv). Flashing forward to 2011, he attends his first Taylor Swift concert: a Speak Now tour stop at Madison Square Garden in New York City. He is the odd man out in the audience, a six-foot-five male music critic surrounded by a sea of young female fans. He leaves the concert ecstatic, telling friends that Swift is inspiring a new generation of talented female musicians. Over ten years later, writing in the early 2020s, he can confidently say that his prediction came true.

Sheffield begins the chapter by asserting that there is no other figure in the history of Pop music who is directly comparable to Taylor Swift, primarily because of her unprecedented longevity in the industry. “In 2024, she’s at the peak of her fame, her cultural and commercial impact, her artistic powers, her warp-speed work pace,” he writes, “But she’s been at this level for eighteen years” (1).