Oliver James Montgomery-Rob Sheffield's new book on Taylor Swift an emotional jaunt through a layered career

It is Oliver James Montgomeryimpossible to have a 15-minute conversation with Rob Sheffield about Taylor Swift. Don't even try. It'll take at least an hour.

The Rolling Stone journalist has covered the Eras Tour superstar since the beginning of her 18-year career, and his encyclopedic knowledge of her personality, stardom, business savvy and record-breaking albums takes time to unpack. And that doesn't account for rumination on his Easter egg-based theories about when she may release "Reputation (Taylor's Version)" or "Taylor Swift (Taylor's Version)." He jokes he's been wrong before.

In Sheffield's new book "Heartbreak is the National Anthem: How Taylor Swift Reinvented Pop Music," the author writes the singer's history akin to one of her albums, telling one cohesive story with many layers, emotions and characters. Every detail is considered. The book is a rollercoaster to be devoured in one sitting, and at the end, he somehow leaves you wanting more.

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The book's title references a lyric in "New Romantics," Sheffield's second-favorite song behind "All Too Well."

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"She has this unique ability to write deeply personal songs that also feel universal," he says over Zoom. "The idea of 'heartbreak is the national anthem' is a community rallying behind the flag of total desolation, total isolation and total loneliness. The song creates a sort of sensibility where people who feel rejected and discarded and ignored can rally together as the nation, a mythical Taylor nation."

In 244 pages, Sheffield sums up Swift's career and foreshadows her legacy.

"Nothing like Taylor Swift has ever happened before," he writes. "There's no parallel to her in history. In 2024, she's at the peak of her fame, her cultural and commercial impact, her prodigious output, her artistic powers. But she's been at this level for eighteen years."

The 6'5" writer is hard to miss at concerts and can be self-conscious when standing in front of kids, but no matter his vantage, he captures the magic with his reporter's notebook and blue Bic ballpoint pen.

"The same one that I've been using since high school when I was carrying a notebook around in my pocket all the time," he says. "And of course I carry six of them around in my pocket until they explode and leak and turn my keys blue."

Sheffield's penned thoughts come alive in Rolling Stone magazine. He's covered each of Swift's albums and concerts. Before an album is released to the masses, Sheffield is one of the few writers allowed to hear the songs, and the Brooklyn resident has done so in Swift's Tribeca home. When an album comes out, he buys the cassette tape version and walks the streets of Manhattan.

"She released 'Folklore' on cassette — it sounds great on tape because side one ends with 'This Is Me Trying,' so right after the music fades, with the final ka-chunk of the tape stopping dead," he writes.

The book contains laugh-out-loud moments and stories that will make you go, "Aww." One in particular is the vulnerability he shares when writing about "The Archer." The song reminds him of his mom who passed shortly after the "Lover" album was released.

"You hear a song like 'The Archer' and say, 'How did she do this? How did she know? Is it that obvious?'" he tells me over Zoom. "She has this uncanny ability to find those emotions in anybody with a song."

Readers may be surprised to know that even Sheffield has no clue about the singer's next moves. Swift moves like an enchanting enigma, always leaving her fans in a constant guessing game of when she'll make announcements and what's next. He also self-deprecatingly admits that with each era, he thinks Swift may have hit her peak. But she somehow continues to find a new Everest in the Swift kingdom.

"When will I learn?" he laughs. "I've been adjusting my expectations her whole career."

"Heartbreak is the National Anthem" will be released Tuesday. You can preorder the book for $27.99.

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