If you’re writing a book about every song an artist has ever written, you ideally want to publish it during a time when you know that said artist isn’t going to suddenly drop new music and instantly render the information outdated. But when that book is about Taylor Swift, that threat can never really be at zero. 

Enter “Taylor Swift: The Stories Behind The Songs” (out Sept. 24 in the U.S.), a chronology of every single song in Swift’s discography — yes, even her “Saturday Night Live” monologue song.

Author Annie Zaleski, a music journalist and an early fan of Swift, tells Taypedia she wrote the book between November 2023 and January 2024 and was on high alert the whole time in case Reputation (Taylor’s Version) dropped and she needed to suddenly update her writing. 

“I finished the book and we’re like, ‘OK, hopefully we’re in the clear,’ ” Zaleski recalls. “And then the Grammys happened.” 

It was at the 2024 Grammys, held less than a month after Zaleski was supposed to be done with the book, where Swift announced her 11th studio album, The Tortured Poets Department. 

TTPD did end up making it in the book, but instead of an additional 31 pages of song-by-song breakdowns, it’s a four-page analysis of the album as a whole. It’s fitting that the most prolific songwriter of her generation literally out-wrote the pace of the book about the unrelenting pace of her songwriting. 

“People say, ‘wow, that must have been a lot.’ And it was a lot, but it was also such a joy to go back and listen to records I haven’t listened to in a while and look back on where she has been,” Zaleski says. 

And Swift has been many places since her debut album arrived 17 years ago, from country to pop to folk and back again; from singing the National Anthem at hometown sporting events to executing the highest-concert tour of all time; from writing love songs in her high school math class to becoming the first and only artists to win album of the year four times at the Grammys. 

Through all of those stages and changes and eras, one thing remains, Zaleski argues in the book: “More often than not, Swift’s songs bubble with determined optimism. Even in her darkest moments, she’s always maintained that brighter days are ahead.” 

Yes, there are the breakup songs — Zaleski’s manuscript chronicles plenty of torrid affairs, all the way from Joe Jonas to Joe Alwyn and Matt Healy. Even Travis Kelce makes an appearance, with a full-page photo of him and Swift embracing on the field of the 2023 AFC Championship game. It’s alongside the breakdown of the song “Karma,” which Swift has adapted from a song about ex Joe Alwyn to one about her NFL man by replacing the line “Karma is the guy on the screen / coming straight home to me” to “Karma is the guy on the Chiefs.” 

But Taylor Swift: The Stories Behind The Songs isn’t about assigning each of Swift’s songs to the love affairs that inspired them. It’s about appreciating an enormous (and still growing) body of work and the artist’s storytelling abilities that continue to captivate and inspire a generation of listeners. 

‘She’s so resilient’, Zaleski says. ‘That’s the one thing that stood out to me as I was looking at everything. Even at the lowest moments of songs… there’s always a sense that maybe around the corner, something good will happen. There’s always that hope that life is going to turn around.’

“She’s so resilient,” Zaleski says. “That’s the one thing that stood out to me as I was looking at everything. Even at the lowest moments of songs… there’s always a sense that maybe around the corner, something good will happen. There’s always that hope that life is going to turn around.” 

Listening back to the earlier albums, Zaleski was reminded of “how sophisticated” and “perceptive” Swift’s writing was.  

“For newer fans, I think people might be surprised at how prolific she was as a teenager,” Zaleski says. “She had such a distinctive and defined voice and knew so much about what she wanted to write about and who she wanted to be from very early on. I think people forget that now just because she’s been in the business for so long.”

Take “Fifteen,” from Fearless, which dropped in 2008, when Swift was just 18. It chronicles her first day of high school, with all the hope, heartbreak and honesty that fans have come to expect from her songwriting. 

“The way her perspective in that song changes from the contemporary perspective of the teenager walking through the door on the first day of school, but then having the ability to look back and tell her younger self, ‘hey, this isn’t the end-all, be-all.’ What an unbelievably complicated and emotionally rich song to be writing at such a young age,” Zaleski says.

Fast forward through nearly two decades of music, Swift’s candor and creativity continues to produce songs that are “masterclasses in storytelling, chronicling the ups and downs of growing up and trying to find yourself,” Zaleski writes.

What’s next for Swift? The Eras Tour is scheduled to wrap up in December. Zaleski hopes she takes some time to “decompress” afterward. But knowing Swift, she must have eyes on the next project, be it releasing a re-record or dropping TS 12. Zaleski wonders if a rock or stripped-down acoustic record might be in her future — and if producer Jack Antonoff will continue to be Swift’s main collaborator, given how they “really bring out the best in each other and (are) just really on the same creative wavelength.” 

“The Eras Tour is such a cherry on top of her career sundae. It’s such a big achievement,” Zaleski says. “It’ll be very interesting to see where she goes, because the sky’s the limit now.”

Buy Annie’s book, Taylor Swift: The Stories Behind the Songs or follow her on Twitter (X).