Author Talk – Taylor Swift: The Stories Behind The Songs
Award-winning music journalist Annie Zaleski returned to 360°Sound to talk about her new book Taylor Swift: The Stories Behind The Songs, a comprehensive review of the Swift songbook. The 240-page book covers Swift’s 11 studio albums and more than 200 songs, beginning with her debut single “Tim McGraw” from 2006 and ending with last year’s The Tortured Poets Department. Zaleski is also the author of illustrated biographies on Lady Gaga and P!nk, as well as Duran Duran’s Rio for the 33 1/3 series.
Editor’s Note: This interview has been edited for length and clarity. Scroll to the bottom to view the full video interview.

360°Sound: Please start by telling us how Taylor Swift: The Stories Behind the Songs came to be.
Annie Zaleski: A couple years ago, I got approached by a publisher who was looking for someone to write a book on Taylor Swift. I had written about Swift fairly extensively. They somehow found me, and I ended up talking to them, and I was like, “You want me to do a book on Taylor Swift? Okay, how soon do you need it?” I am such a fan of her work, and so it was just a real joy to dig into everything she’s ever done.
What would be an example of a Swift song that you thought had a particularly interesting backstory?
One of my favorite Swift songs is the “Last Great American Dynasty” from Folklore. There’s a whole bunch of different stories to it. She bought a house in Rhode Island, and it happened to be owned by this really fascinating woman named Rebekah Harkness. She was married to different people, and she was an aspiring musician. When Taylor bought the house, she learned all about Rebekah, and ended up becoming an expert on her life. She wrote this song, lightly fictionalizing some details about Rebecca having this marvelous time ruining everything, and just having these amazing parties. And then she twists the song and talks about herself because she bought the house.
I had the opportunity to research Rebekah’s real life, and I dug up some amazing stuff. You could see why Taylor gravitated toward her. She was just a real character. Reading about that illustrated the detail that goes into Taylor’s songwriting and just what a brilliant song that is.
What are some ways in which Swift’s songwriting has evolved over the years?
First, on just a surface level, musically, she was pretty straight up country at the start. And then over time, she has really come to embrace a lot of different genres, mainstream pop music but also a little bit more folk music, electronic music, and rock music. In recent times, I think she’s settled into this modern pop groove that has folk flourishes, electronic flourishes, indie rock, and all sorts of different things.
From a writing standpoint, the sophistication was really evident. When she started, she was so young. She was writing about what she knew, which was a lot about her life as a teenager and the things she was going through. And you really see her start to deepen as a songwriter. In some of the songs she wrote, she was almost having conversations with herself about them. She uses a lot of the same imagery throughout, so there’s a real cohesion to it. She has dabbled in fiction a little bit and brought in more storytelling in terms of making these rich characters. There are some wonderful story songs on Folklore and Evermore.
I think of a song like “Anti Hero,” which is one of her newer era songs. She’s talking a lot about depression and insecurity and self-loathing and anxiety. Those are very adult, sophisticated things that you don’t necessarily hear in a lot of pop songs, and she’s really embracing that vulnerability. It was just so striking seeing her growth, and when you listen to her entire catalog from front to back, you really see the progression. It’s just a real delight to see.
“Anti-Hero” was one of her biggest hits, spending eight weeks at No. 1. What do you think resonated with people about that song?
I think the whole chorus – “It’s me, I’m the problem, It’s me” – first off, that’s exceedingly catchy. But second off, I think it’s really relatable to a lot of people. When you’re at your lowest moments and you’re feeling like you can’t get anything done, or you’re having a hard time, you really get stuck on, “It’s my problem, it’s not the world’s problem,” like, “something is wrong with me.” That’s a deceptively cheery thing. If you see it live, she’s waving to the audience. But there’s a real layer of sadness, and it’s very interesting, it’s a lot more layers than you might think. She’s talking about it being in the middle of the night and having these doubts.
In recent years, the song “I Can Do It With a Broken Heart,” is another one where she’s talking about these really sad, difficult moments in her life, and it’s this really upbeat pop song. There’s such a tradition of that. I think of the Smiths, and obviously, Taylor’s music is nothing like the Smiths, but they wrote all these really upbeat songs with these really morose lyrics. She’s dabbling in a little bit of that as well.
If you were able to interview her about her newer music, what song would you like to ask her about?
I love the song “Clara Bow.” That’s another one with a really rich backstory. Clara was an actress, and she mentioned Stevie Nicks in the song. And that was another one where she’s mentioning all of these women throughout history and then brings it back to herself. How did you come up with that? How did you land on Clara? What was your inspiration? Who introduced you to her? And how did you come on with the Stevie Nicks bit?
“You’re On Your Own Kid” really became such a phenomenon because of the line about friendship bracelets. For the Eras tour, people started making friendship bracelets and trading them, and that just became a phenomenon. Where did you come up with that? How did that song come together? Because that’s another really heartbreaking song in terms of trying to find your place in the world and figure out what you want to be and what you have to do to get there.
Also, “So High School,” I just love the sound of that. If she could make a record that sounds like Soccer Mommy and modern indie rock, I would love an entire record of that. I think a lot of people have wanted her to indulge her not-so-inner emo fan. She’s a big fan of the mid-2000s emo movement, and just her doing a rock album like that, I think would go over really well because I think she’s really natural at that.
What would be your final pitch for the Swifties who may be interested in picking up the book?
I guarantee you that you will probably learn something you didn’t know, even if you think you know everything. It’s a real celebration of her catalog. It mentions the tabloids a little bit, but it’s absolutely about her music and how she wrote the songs, why she wrote the songs, and how they came together. It really honors that. It’s definitely trying to give her respect as a songwriter and underscore why she is such a generational talent. It’s illustrated with lots of full-color, high-quality photos as well.
Learn more about Cleveland’s favorite music freelancer on her website: anniez.com
