Are Taylor Swift fans masochists? This author believes so — and says that’s part of the fun

Rob Sheffield, a writer and contributing editor at Rolling Stone, has chronicled Taylor Swift since the breathless first few years of her career. In his upcoming book, “Heartbreak Is the National Anthem: How Taylor Swift Reinvented Pop Music,” he recalls the first Swift track he ever heard: “Our Song,” which in 2007 played through his kitchen radio while he prepared a grilled cheese sandwich.
“That song is my origin story,” Sheffield told the Star. “That was my conversion experience. I was shocked by how great the song was, and how clever it was. I remember thinking, ‘I hope she has some other good songs besides this one,’ and I remember thinking that if this was her only good song, it was something to be proud of.”
Of course, history has proven repeatedly that Swift can write songs as good as — and much better than — the earnestly bubbly closing track from her debut album. As a journalist, Sheffield has been there to document Swift’s rise to the top of the pop heap, along with the missed opportunities and stumbles along the way.
The Star sat down with Sheffield for a wide-ranging interview. What follows is a lightly edited transcript of that nerd-out, er, conversation.
It’s exciting. I mean, (Swift) is always doing stuff. Every time I think I might know what’s happening in her world or for the foreseeable future, she does something amazing. She just announced she’s releasing a book about the Eras Tour yesterday.
My last book was about the Beatles, and the one before that was about David Bowie. I’m used to writing these stories about these long careers that have definite endings. With her, it’s 18 years of constant activity. She’s always throwing new stuff into the mix.
Well, there’s no end to the story. You can’t predict what it’s going to be like in a month if there’s so much chaos and turmoil involved. One of her album releases is always going on — we’re still hanging on for an announcement of her rerecording of “Reputation” after all this time. For nobody else is there so much torture and exhaustion and trauma to be a fan. That’s part of what we love about her.
That was crazy. For “The Tortured Poets Department,” I got the album a few days early, so I wrote my review after listening to it non-stop for three days. My review went live at midnight on the night it came out.
But then a couple hours later, this new album dropped — I had a 10-minute warning that it was about to happen, and I was like, “You’ve got to be kidding me.” And sure enough, 10 minutes later, new music dropped at 2 a.m. I’d already had a long, full day, but I put on a pot of coffee and listened to these 15 new songs. And I absolutely loved it.
Right? What a song. It’s exactly like “New Year’s Day” on (2017’s) “Reputation.” It ends the album so perfectly. There’s a complete beginning, middle and end on the album, but those songs on the second half (of the bonus “Tortured Poets Department” album) are just … wow. “The Prophecy” is the one that destroys me. I love “Peter” and “I Look in People’s Windows.” I absolutely love the second half of that album, and again, I was so unprepared for it. I got a text at 1:50 a.m. asking if I was still awake.
I love that she rolled out that album in the most difficult possible way for us, the way designed to make us most miserable. She just loves to do it that way.
Yeah, nobody else in the history of pop music has ever had more fun making it so miserable to be a fan.
Swift has always gone for such elaborate coding in her music — this isn’t something she picked up as an adult. It’s nuts that from the very beginning she was hiding secret messages in her CD booklets. She was a brand-new country singer when she started doing that. She was hiding these elaborate, Beatles-inspired mysteries right there in her first album. I just love that she was already that kind of music geek when she was 16.
I wanted to do justice to her as a culture hero, but also as a musical genius. Something I always found really strange, and sometimes very frustrating, was that when people wrote about her, they wrote about the image and the celebrity life and the boyfriends and the fashion. But her actual music was easier for people to overlook. Even now, if you go back and read what people were writing about her early work, even when their thoughts are positive, there’s a sort of condescension to it, where they’re not really reckoning with the artistry.
Oh my god, the Eras Tour. That show could have been half as long, and everybody would have been perfectly happy. There was no need for her to make it as epic as she made it; one of my favourite moments is when she does the 10-minute version of “All Too Well” and everyone is wiped out from shock, but it’s only halfway through the show. There’s almost another two hours to go after that song.
It’s an extraordinarily long show, and an extraordinarily varied show. It’s so full of tiny details, and it’s just fascinating to me that she’s driven on this almost Captain Ahab level to overdo absolutely everything. I love that about her. (It’s) what makes her so incredibly weird and scary and mysterious. She’ll never settle for good enough.
Yes, I had to go to her house. Normally, you get a watermarked download to preview new music. Normally no one’s watching me with binoculars to make sure I’m not making a copy of it. It’s hilarious — I’ve never had another experience like that, where I’ve had to go to the artist’s home to hear the album, just to make sure there’s no breaches in security. That’s just absolutely nuts.
It’s such a wonderful challenge writing about her all the time. She’s never going to give you a chance to repeat what you thought about her before. No artist has been more fun to write about, because it’s impossible to predict what her next move might be, or even when it might be. When you write about her, you come in with a certain idea of the things you want to say, and they just change the deeper you get into the music, because there’s so many surprises embedded in it.
When I began the book, she was in her “Folklore” and “Evermore” era. She was still with (British actor Joe Alwyn). I thought that was the context of the book. It’s funny how many things have changed — how many decisions and realignments she’s made since then. There are always surprises, and her songs from the past are constantly changing, too. With each passing album, you see her in new ways.