Rob Sheffield, Taylor Swift. Getty Images (2)

The song “All Too Well” has become one of Taylor Swift’s most iconic and beloved hits, but the tune didn’t always feel like a winner to Swift.

In his new book Heartbreak Is the National Anthem: How Taylor Swift Reinvented Pop Music, Rolling Stone journalist Rob Sheffield revealed how his love for the song actually rubbed off on the pop star.

“I’m constantly updating the [Rolling Stone ranking of Swift’s songs], moving songs up or down as they change for me over time, always cheating to keep ‘Fifteen’ at fifteen,” Sheffield, 58, writes in the book. “But two things will never change: ‘All Too Well’ at number one, ‘Bad Blood’ at the bottom.”

He went on to recall a conversation he shared with Swift, 34, backstage on opening night of the Reputation Stadium Tour in Glendale, Arizona, in May 2018. “She warned me backstage she had a surprise. ‘I added ‘All Too Well’ to the set because of you,’ she said. ‘It’s number one on your list,’” he said Swift told him. “’You changed my mind about that song. You convinced me it was more than just a Red Tour song.’”

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Sheffield continues: “My trusty poker face must have failed me, because she looked concerned and asked, ‘Is it okay I told you this?’ She sang a solo acoustic-guitar version that night — it was rare, I was there.”

As Sheffield notes, Swift proceeded to play “All Too Well” during the show’s surprise song set a handful of times throughout the tour, while his least favorite track, the 1989 track “Bad Blood,” got a permanent spot on the tour’s setlist. “Just in case you’ve got her confused with somebody who listens to opinions,” he quips.

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Heartbreak Is the National Anthem: How Taylor Swift Reinvented Pop Music, which hit bookshelves on Tuesday, November 12, serves as Sheffield’s deep-dive into Swift’s decades-long career. The journalist goes into deep detail about his love for “All Too Well,” which is heavily rumored to be about Swift’s brief relationship with ex, Jake Gyllenhaal.

“I’ve kept listening, writing about it, butchering it at karaoke. It goes where I go,” he writes. “When she first announced she was unleashing the long-rumored ten-minute version, I hoped it might add a cool footnote to my favorite song. But now it’s just the song.”

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Swift released “All Too Well” as a part of her fourth studio album, Red, in 2012 and performed it throughout The Red Tour, which ran from 2013 to 2014. Much like the Reputation tour, Swift also pulled out the fan-favorite track for a Los Angeles stop on the 1989 World Tour in 2015.

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The song gained more fame when Swift released her Red (Taylor’s Version) rerecorded album in 2021, which featured the long-awaited 10-minute version of “All Too Well.” She adapted the lengthy song into a 2021 short film starring Sadie Sink and Dylan O’Brien and continues to perform the track in its entirety during the Red set of her record-breaking Eras Tour, which concludes next month in Canada.

“It destroys crowds every night on the Eras Tour. It set a new record as the longest number-one hit in history, dethroning ‘American Pie.’ (The courtroom was adjourned; the scarf was not returned.),” Sheffield writes. “But it only exists because fans called her bluff — after she mentioned the original draft, people kept asking about it, as if she had it hidden in a sock drawer. She must have wished many times that she’d kept her mouth shut. But all this talk inspired her to go back and open up a story she thought was finished. Just imagine, these extra verses were sitting there for years gathering dust, just waiting for their time.”