When Rolling Stone music critic Rob Sheffield called me from New York City, I didn’t spend any time with softball questions or developing rapport. I jumped right in with my hardest-hitting question about his new book, Heartbreak Is the National Anthem: How Taylor Swift Reinvented Pop Music: Did he write an essay about the 1989 bonus track “New Romantics” to drive listeners to play the song—and sing-scream his book title, a “New Romantics” lyric—on repeat?

I’m serious, though; immediately after reading the chapter, I cranked up my car stereo and belted out “New Romantics” three times in a row. Sheffield laughs; he understands.

“I think it was more that I was shouting out the title of the book while I was writing. That song is absolutely nuts, so perfect in terms of a statement of her worldview, a statement of her entire philosophy of life,” he says.

“Writing this book was going deeper into the Taylor Swift mysteries that have been perplexing us all over the years”

That outlook on Taylor Swift’s music shows up throughout Sheffield’s latest book and repeatedly during our conversation. And it’s clear from the outset of Heartbreak that Sheffield is a Swiftie, and his fellow Swifties will find lots to love here. But it’s not just for us: I could hand this book to a casual music fan who wants to understand the fuss or to a lifelong Swiftie. They would both leave with something new.

It’s hard to discuss the book and Sheffield’s motivation without slipping into fan talk. Heartbreak is relatable in part because of the connection to “all the Taylors you’ve ever been,” as Sheffield writes about the rhapsodic, parasocial reaction to the star’s Eras Tour.

“These songs, because they’re so emotionally intense, they catch you at the moment you are,” he says. “Even if the songs aren’t describing the situations you’re going through on a superficial level, they speak to the emotional truths. She’s got an uncanny knack for that.”

Sheffield leans in to that connection, crafting a book that isn’t exactly a biography, nor precisely a fan memoir or exclusively a cultural analysis. He uses all three of these approaches. It’s the same process he used for two of his most recent titles, 2016’s On Bowie and Dreaming the Beatles the following year. Sheffield’s love of his subject’s music is always part of the story, yet he goes beyond his own perspective.

 “No one listens to music more closely and are tougher to con than the teenage girl fans,”

“Like I said in my Beatles book,” Sheffield says, “I wasn’t writing a behind-the-music book, not where the music came from, but where it went—how it created the world we’re living in.” Significantly, he wrote about Bowie after his death and the Beatles long after the band’s dissolution. As an artist still in motion, Taylor Swift presented a new challenge: “As I was writing, she was always a step ahead of me.”

Those unfamiliar with Sheffield’s work might be surprised by a 50-something, male Rolling Stone writer following the avatar of American girlhood. They might even think he’s cashing in on the moment when Swift seems to be the world’s biggest celebrity. Bowie, the Beatles and other classic acts might seem more obvious choices. But Sheffield has been a Swiftie longer than I have—and probably longer than you, too.

“For me, it all comes down to ‘Our Song,’ ” he says of the 2007 single, Swift’s third. “Oh my gosh, I couldn’t believe my ears. . . . The way it’s this teenage girl saying, ‘I’ve heard every song ever made and ever recorded, and they’re not good enough. I’m just going to have to write my own song that is our song.’ Even before I Googled the singer, I Googled the songwriter.”

Sheffield was startled to find that the songwriter was also the singer—and that she was a teenager. He thought at the time, “Wow, I hope she has another song or two that’s this good.” He laughs. “Little did I know. Little did any of us know.”

Swift has written more than a couple of smash singles, and in fact, you can read Rob’s complete song-by-song ranking on Rolling Stone’s website. He updates it with each new release—but he always cheats to keep “Fifteen” at No. 15. Heartbreak is filled with knowing allusions to Taylor’s lyrics and catalog, which continued growing as the book was underway.

Sheffield began writing just before Swift’s record-setting Eras Tour began in March 2023. Why then? “For a while, I was thinking in terms of, wow, when she sort of hits a plateau level, that’ll be the time to take it all in,” he says. “When she stops innovating and inventing on a week-to-week basis, that’s the time to take stock.”

It became clear that Swift wasn’t slowing down anytime soon, so Sheffield took the plunge anyway. “I was trying to do justice to where she was at that point; at that point, Midnights was the new album,” he says. She’s released an album and re-released two others since then (and with Swift, there’s no telling—there could be another before this interview publishes). “By the time this book is out, she’ll have done something that demands another chapter,” Sheffield says. “She’s been on this hot streak for the past 18 years, and it’s rare for anyone to have a hot streak like this for one year.”

“She always wanted those songs to make a mess in your heart and your mind and keep making a mess.”

Sheffield continued to marinate in Swift’s music as he worked on the book, attending three consecutive shows early in the Eras Tour. “After three nights, I was absolutely ready for a wheelchair and a feeding tube,” he recalls. “I said, how is she even possibly functional this week given that all I did was stand in the audience and scream and sing along? And as we now know, she was not only doing this but making The Tortured Poets Department”—her latest album as of this writing—”between shows, which was just absolutely insane.”

Sheffield had plenty of material to draw from. “I’ve been writing about her for so long and pondering this stuff for so long and reading about her for so long—and reading since the early days, when almost everything written about her was condescending and dismissive. You hate to say, but that’s how she was written about for years,” he says. “Writing this book was going deeper into the Taylor Swift mysteries that have been perplexing us all over the years. I wasn’t trying to solve these mysteries, but just understand them a little better. A little deeper. Really, that’s the process for me. I was listening to the music. But I’m always listening to all those records.”

Heartbreak recounts Swift’s career with tremendous respect, and Sheffield’s knowledge of both her discography and the music she admires is clear. He draws connections to many artists whose influence shows up in her music: “She was a teenage prodigy who had studied all the greats,” including Carole King, Joni Mitchell, Bruce Springsteen, Prince, the Beatles and more. “It was so fascinating that this was someone who was so early in her career but was determined to be on an all-time great historic album.”

Sheffield also analyzes the world’s reaction to Swift, who has often been dismissed with derision, particularly earlier in her career: “People are always saying, ‘Oh she’s good for her age.’ But who are the people older than her who are supposedly writing better pop records?”

The condescending attitude also loops in teen girls, which doesn’t sit well with Sheffield, who is quick to note that Swift’s career started when she was a teenager. Now in her mid-30s, Swift continues to put teen girls first. Those teens are not only the secret to Swift’s success. They’ve been behind most artists with multigenerational fans.

“The teenage girls are just the most sophisticated listeners,” says SheffieldSheffied. “No one listens to music more closely and are tougher to con than the teenage girl fans,” he says. “In case you didn’t learn this from the Beatles or Bob Dylan or David Bowie or whoever, the teenage girls are getting things that the rest of the audience doesn’t.”

Heartbreak is an ode not only to the artist who sees those listeners as paramount, but also to the industry she’s reshaped in her image. Many of Swift’s fans have grown up with her, Sheffield notes, and that’s a rarity. “Ex-Swiftie is not a category, really. It’s not a phase that people grow out of, which was what was already predicted in the early days.”

Read our review of ‘Heartbreak Is the National Anthem’ by Rob Sheffield.

Today’s pop charts reflect this influence, too, with young women such as Sabrina Carpenter, Billie Eilish and Chappell Roan releasing 2024’s songs of the summer. “That’s what pop music is now,” says Sheffield. “Taylor very much remade pop music in her image. The idea that pop music by women, for women is pop music. It’s not a subgenre or a sidecar to the story. It is the story. That’s an astoundingly huge innovation.”

And Swift’s music has given these musicians and their fans room to revel in the entire emotional experience of a song. “She was never writing songs that ended as songs. [It isn’t] ‘oh, what an elegantly turned verse, what an expertly turned chorus,’ ” Sheffield says. “She always wanted those songs to make a mess in your heart and your mind and keep making a mess.”

Heartbreak is a love letter to the songs that have created that mess in Sheffield’s own heart, and an invitation to bathe in the music. Swifties, in particular, are likely to find themselves queuing up track after track as they read—at least, this one did—and join Sheffield and me in shout-singing his book’s title again and again.

Photo of Rob Sheffield by Marisa-Bettencourt.