Rolling Stone contributing editor and longtime local resident Rob Sheffield has written tomes on David Bowie and the Beatles, but his latest subject might be his most daunting yet—and she’s still relatively early in her career.
Since Taylor Swift first burst onto the scene with a mop of curly hair and teardrops on her guitar, she has consistently upped the ante for all of pop music (not to mention, the music industry at large) with her wise-beyond-her-years confessional songwriting and fluid movement between genres and styles. Sheffield, a Swiftie to the core, has been covering her stratospheric rise since 2007. His latest book, Heartbreak Is the National Anthem: How Taylor Swift Reinvented Pop Music, cements Swift’s legacy as one of the all-time greats.
Greenpoint’s preeminent Swift expert (and arguably, the world’s) spoke to Greenpointers about his new book, which you can preorder from WORD Bookstore here and get tickets to a November 12 book release event here.
This interview has been condensed and edited for clarity.
Your book comes out on November 12, and you’re kicking it off with an event at Brooklyn Brewery (79 N 11th St.) with WORD. How does it feel to be doing this event in Greenpoint?
Oh my gosh, I love it. I wouldn’t want to start it anywhere else. It’s basically where I’ve started all my books, ever since WORD (126 Franklin St.) opened. I remember before there was WORD, there was nothing like WORD before, there was no English language bookshop, there were a few Polish bookshops.
For a long time, our Greenpoint ritual was we’d go to the Greenpoint Coffee House, way up on Franklin, on Saturday afternoons for omelets, and on the way there, I’d just stop at WORD and buy books to read while we ate our omelets. It was like a miracle for WORD to suddenly land in our neighborhood. I just love that place. That’s where I do all my book shopping.
Take us through your journey into becoming a Swiftie. When did you first encounter Taylor Swift, and what turned you into a mega fan?
It was the song “Our Song.” That was my origin story. I wasn’t even consciously listening to music, I was making myself a grilled cheese sandwich. And I had the TV on, because I would eat lunch and watch reruns on the CW network. And they would play pop songs sometimes between shows, and I heard this song coming out of the TV, and it was “Our Song,” and I had no idea who this singer was. But the song completely blew my mind. I love that she spends the whole song talking about, there isn’t a song that does justice to the depth of my feelings. Me as a teenage girl, I have so many hopes and emotions, and no song does justice to them, and I’ve heard every album, listened to the radio, but this song doesn’t exist, so I have to write it myself, and the song ends with her sitting down in her room and writing her song. I just thought “This is totally genius!”
I loved the chorus, I loved her voice, I loved the banjo, and I immediately googled to see where did the song come from—I was more interested in the songwriter than the singer—and thought, how bizarre, the singer and the songwriter are the same person! That just doesn’t happen in country music, at the time. I also couldn’t believe, wow, this person is just starting out, this is her first album, and she’s only a teenager, and I remember thinking, I hope this isn’t the only song she’s got, I hope she has one or two more. Little did I know…
I was a raving Taylor Swift fan from hearing that song for the first time.
There’s certainly no shortage of lyrics that could have made a good book title. Did you always envision “Heartbreak Is the National Anthem” or did you consider other options?
I loved that title from the beginning. It’s funny, I had one other title that I was thinking about, which is from another song, “Holy Ground.” The title I was thinking of was “never looking down,” and yet, “heartbreak is the national anthem” just had to be the title. “New Romantics” is a song I love so much and “heartbreak is the national anthem,” something about that line, the way it goes from heartbreak and loneliness and isolation to this community that forms around that. That is a song that sort of rallies people together, a heartbroken national anthem, to me that captures all the grand and weird contradictions of Taylor Swift in one line. So I always wanted that to be the title.
What are some of the challenges writing about someone in the prime of their career versus a legacy artist like the Beatles or Bowie? Books take a long time to put together, but there’s news about Taylor Swift every day, so I was wondering if you at any point had to sort of establish parameters like, ok I can’t even get into the Travis Kelce of it all.
Oh my gosh, it is so much harder. Unbelievable. I had friends often say, “This is the last time I write a book about somebody who’s still alive!” Especially when people write a lot of biographies, they sometimes say that. I always assumed they were joking, but oh my gosh, it’s so much harder! I love writing about really long complicated stories with long afterlives. I wrote [On Bowie] after he passed away, but in many ways, the afterlife is the star of that book. For the Beatles, even though they’ve been broken up for 50 years, I was writing about their afterlife as much as their existence but still, these were stories that were, on some level, closed.
With Taylor, there is new, crazy stuff every single day! She just announced her book. Part of the experience of writing this book was the madness of knowing constantly that I was telling stories, writing things that were going to be totally transformed by the time the book came out. She’s always been just impossible to pin down. I’ve always known that as a journalist writing about her day to day over the past 18 years, and yet, for a book, every time I think, yes, this is a great theme in her career or a great character in her career, there’s always more chapters that she adds to it. Honestly, I could have kept writing this book forever, and I still haven’t caught up, because she’s constantly changing.
There’s one part where I was writing about her relationship with Stevie Nicks, which is such a long and fascinating artistic sisterhood. I honestly thought I had reached the end of that arc, was very happy to have that part of the story done. I sent that to my editor, and then two days later, Stevie Nicks shows up to the Eras tour, and Taylor gives this whole speech about how Stevie gave creative freedom to all the female artists out there, including her. And I just thought, unbelievable, this is obsolete already [laughs]! But that’s part of the excitement about writing about the kind of pop star that Taylor Swift is, who is someone who never slows down, never settles down, doesn’t repeat herself.
Famously, you’ve ranked and reranked every Taylor Swift song for Rolling Stone. “august” in the top 5 is, in my eyes, inspired and correct. In doing that exercise, which songs surprised you the most, whether that be where they ended up being placed or a song that you might have previously underestimated?
Well, that happens all the time. Songs move around a lot for me, as with, I think 99% of people who listen to Taylor Swift’s music, because there’s a song that jumps you at this moment or that moment and says “No, me actually, I’m the best song ever written in the history of music!” And then a few hours later, it’ll be the same feeling with a totally different song. For her, it’s a thing where these songs are always rising, always falling. Some of them, I’ll go years at a time without appreciating, until some other song sort of updates the story. I used to think that “You’re Losing Me” was a really nice song. I thought it was good. I didn’t think it was mediocre, I thought it was good, I didn’t think it was great, I thought it was good. And then Tortured Poets comes out and suddenly it puts that song in such a dramatic context. That song’s not on the album, but that album sort of gives a whole new perspective to the song that she did a year earlier, now that’s one of the songs I’ve played the most this year.
Sometimes a song, you hear it for years, and you like it, and then one day, it goes from like to love. I had that with “You Are in Love.” For years, my niece would rage against my Taylor Swift rankings because I always had “You Are in Love” too low. My nieces are always very successfully changing my mind about Taylor’s music and her contributions to culture. It was funny for me that one night about a year ago, the switch just flipped for me, and “You Are in Love” became a song that I needed to hear all the time, constantly. It’s not like that song was new to me, but these songs, they’re so unpredictable, they are mischievous, and they are exhausting. You think you’re finished with a song, and she’s never finished with a song, so why should you be?
She’s always revisting and adding to the lore.
For which songs are most surprising, to me, “All Too Well” is the heart of her music, which is why it’s the song at the heart of the book. It’s really the song that the rest of the book rotates back. I had a chapter about “All Too Well” that I put at chapter 5, because it needed to be track 5 in the book, even though it’s chronologically not necessarily where that chapter begins, but it had to be track 5. For me, that is the ultimate Taylor Swift song. It was already the ultimate Taylor Swift song when she released it, and yet, that song has just taken on so many lives since then. She thought she was finished telling the story. She didn’t particularly like singing that song—she stopped doing it live for years at a time. It was a song that she said was just too personal and too painful for her, and she didn’t talk about it, and she didn’t revive it live, and she treated it like it was a song she was done with.
People just wouldn’t let it go, because she told the story of how that was originally a ten-minute song that got edited down to the version we know, and of course, she must have regretted saying that so many times because people just kept asking about it, and she eventually had to break down and admit that the song was in charge of the story, she didn’t own the song anymore, the song was the one calling the shots. She had to go back and see what more there was to the story and sort of let the song tell its own story…To me, that’s the entire Taylor Swift story in that one song.
I’ve been a fan of yours since your days as a VH1 talking head. I’m not sure if you ever see how often my fellow millennial/zillennials reminisce about those “Greatest” or “I Love” shows and how educational they were, and it kind of got me thinking about this idea of monoculture and how it’s kind of not really a thing anymore.
So this is a two part question—is there anything you miss from your earlier days as a music journalist, working within the context of a monoculture? And why is Taylor Swift sort of the last remaining vestige of monoculture?
I don’t know. Monoculture is interesting because there are so many Taylor cultures, and she is so many different kinds of pop stars to so many different people. There are lots of casual fans who know three or four songs. There are people who absolutely loathe Taylor Swift, like, it’s key to their identity. And then there’s people who don’t make it part of their identity, but they just aren’t a fan, and they pray that she would just take a vacation or something. And there’s people that like her a lot, and then there’s people like you or me who are just obsessive about her and obsessive about the details. There’s so many different ways, so many different roles that she can play in a music fan’s life. So it’s almost funny to me that there are all these different Taylor Swifts who are sort of competing with each other. I don’t know if monoculture is the word I’d use, but definitely the idea of a star affects everything else in pop music. Everything else around her is kind of affected by her gravitational force.
That’s just not music at the present, but also, music of the past. She has so changed how people hear music of the past. I don’t think that it’s a coincidence at all that Stevie Nicks is more famous and popular right now than she’s ever been. Stevie Nicks has been around for 60 years at this point making music, and yet, she’s never been heard more clearly by more people and loved more deeply than more people than she is right now, and I think so much because of how Taylor Swift has taught people to hear music, and especially to hear female voices from the past. Joni Mitchell has never been more popular or more revered than honestly by people of your generation—the zillennials, the Gen Z listeners. They get Joni Mitchell on a level that previous generations just didn’t get, not even her own generation—least of all her own generation. That’s very much the Taylor Swift effect. Kate Bush, same way. People hear Kate Bush in a different way now, in large part because of how Taylor has taught people to listen to these female voices from the past, from all over history, as well as all different types of music. Definitely, like, Prince, Bowie, the Beatles, all these major artists that she’s engaged with in her music, partly by using their tricks, partly maybe by doing self-conscious tips of her cap to them. But she’s the kind of artist that transforms the past as well as the present.
Now it seems like things are so siloed and there’s not as many universals for everybody, but Taylor Swift does sort of seem to be one of the few pop culture universals at the moment.
It’s a thing where it always seemed like that was a thing of the past though. In the seventies, people said, yeah it’s a shame that it’s not unified like it was in the sixties. In the eighties, people said, yeah it’s a shame that it’s not unified like it was in the seventies. I’m just naturally very undisposed to that kind of nostalgic sentiment, but I know what you mean by the universals that we used to take for granted. The fact that something like VH1 existed, where it was this nationwide music channel, and it was full of music content—it wasn’t just showing Catfish and Teen Mom on a 24-hour day loop. There was a sense that it would open up history, and in a way, you could turn on MTV or VH1 and sort of hang out with it and pick up music details.
Taylor was a big VH1 fan when she was growing up. She used to watch all the Behind the Music(s). I quote a funny story in the book but there’s a part where she’s doing an interview and she’s maybe like 18 at the time, and she starts explaining to the interviewer, “You know, Bon Jovi was the first 80s rock star who smiled a lot. I learned that from ‘Behind the Music!’” This interviewer is clearly weirded out, like, why is she out here trying to teach me 1980s rock history? But that’s something deep in her personality, that she is the most hardcore music geek, and she really geeks out over the tiniest details.
It’s always changing, how you hear music, how you perceive it, where it comes from, what your source is—that’s always changing. And you can say “Ah, it was better when I was fourteen” or “it was better when I was twenty four!” or “it was better when I was forty four!” but the thing is, it’s always changing, and you can choose to change with it, and to adapt with it. For me, that’s part of where the fun is.
Similar to the death of the monoculture, there’s also been talk of the death of the bridge within pop music. Which, if anyone is keeping the bridge alive, it’s Taylor Swift. What makes a good Taylor Swift bridge? Why is that such a hallmark of her songwriting?
It absolutely is. I think it’s not just because she was good at bridges, but she had such weird bridges. They became very eccentric and very full of her personality, especially around the time of Speak Now, where she’s got so much clout, she’s like “Hey, I could write the entire album myself.” Which is still the only album she’s ever done that. That’s when her bridges start getting really idiosyncratic and sometimes just downright bizarre, where she’ll have the bridge, and then she’ll just start a new song in the bridge. So you’ll get something like “Enchanted,” where there’s already been a bridge to the song. She’s at the end of the song. She’s already got a bridge that she’s sung twice, she doesn’t need to do the bridge again, and yet she takes off into another bridge, just changes it into a whole song with the “Please don’t be in love with someone else” part. It’s like, oh my gosh, she is willing to make a mess out of these!
Some of my favorite Taylor bridges, they’re the ones that go on forever and you’re like, how the hell is she gonna get to the other side of this one? I love the bridge in “Lover,” that’s one where she’s like, I’m just gonna launch into and basically write three or four new songs in the bridge before I get back to the main one.
Right, and I think bridges are so dramatic in a way that really suits her songwriting, and there’s a certain emotional quality that gets heightened.
Yes, so true. The bridge is where she’s like, ok, I’ve established clearly defined emotional parameters, and now I’m just gonna completely trash them and go absolutely wild with my imagination. The bridges really are, often, mini songs of their own. I love the moment in the Eras tour where she’s doing “illicit affairs” and she only does the bridge. She doesn’t even do the rest of the song, she just does that bridge over and over. Everybody’s into it, everybody’s singing along, nobody needs to be guided into it with the verse or the chorus. And then she moves on to another song, but that’s the only part of the song she does, and it makes me think “Oh, wow, maybe she’ll do an entire tour that’s just the Bridges Tour!”
That’s why I wanted there to be a bridge in the book. That’s why I have a whole chapter that’s just “The Bridge,” because that’s how Taylor structures a song. She wouldn’t neglect a bridge, so I told my editor, “I just need a bridge for the book.” And that’s where I talked about lots of her connections to music history, but to me, it was a tribute to her songwriting technique that this bridge just needed to be in the book. The book was just screaming out that it needed a bridge.
What do you hope people take away from the book?
Looking at her just as somebody who has transformed music. She’s transformed the way people hear music. She’s transformed the way people experience music. She’s definitely changed the ways artists make music and release music and think about music. Teenage girl fans who are the hero of this book, and the hero of the Taylor Swift story and the audience that she has always prioritized first above everybody else—she has created a new vision of pop music where the fangirl is the center of it. The fangirl isn’t the footnote to the story of music or a side dish to the story of music. The fangirl, that is the story of music as Taylor has defined it.
It’s so wild to think that when she came along, in the 2000s, when she was a teenager, the whole idea that she was a teenage girl writing her own songs, playing her guitar, singing about her life, her feelings—that was almost like a novelty that she was a young female artist with a guitar just singing her life. And now that’s what pop music is. Look at what’s popular now, from Sabrina to Charli to Chappell to Tinashe to Billie to Olivia. You look at what pop music is in 2024, and it’s largely pop music the way Taylor envisioned it. Taylor committed herself so very early to a vision of pop music and pop music history where fangirl is the hero of the story. She has not just succeeded with that in her art, but she has made that kind of artist the main thing going on in pop music. It’s kind of astounding when you look at the most popular music of 2024 and think just how much of it would have seemed completely unthinkable, especially in commercial terms, before Taylor Swift came along to prove that it was not just feasible, but absolutely going to triumph.
I’m sure the answer is always changing, but at the moment, which Era do you identify as or gravitate toward the most?
My controversial answer is Evermore is my current favorite era. And that comes straight out of the Eras tour. It was such a revelation to me that Evermore was the era that came alive the most in the stadium setting since I think of Evermore as a bunch of lonely-ass acoustic songs about sitting in the woods feeling sad. Yet she does those songs in stadiums and it’s shocking how well they translate to a live stadium setting. It is so surreal to be in a crowd of 80,000 people and the song that she’s dropping on our heads is “marjorie,” and that becomes a stadium singalong? I think of “marjorie” as a super weird, super solitary song. Evermore has always been a favorite of mine. I think my three favorites—Folklore is at the top, Red, Evermore, and maybe Speak Now at number four. But for me, Evermore was the most “era” of the Eras, so I’m completely obsessed with the idea that Evermore is the one.