In all my years in the business, there have been two subjects that could boost your page views like nothing else: Game of Thrones and Taylor Swift. One of them is a massive, multimillion-dollar enterprise filled with violence and betrayal, and the other aired on HBO. For more than a decade, a 31-year-old woman from Wyomissing, Pennsylvania, has found herself at the center of our national conversations about race, gender, celebrity, victimhood, and even the intricacies of recording contract law. And, outside the legions of fans who eat up everything she puts out, no take on her ever stays solid for long. She was a precocious teenager, and the ultimate embodiment of white privilege. She’s been feminism’s worst nightmare, and an advocate for victims of sexual assault. The world’s most famous serial dater, now settled into a long-term relationship with the guy from The Favourite. Some people say she’s a goddess of the alt-right. Other people say she’s Jewish.
And yet, if the word on her has shifted since her debut, it’s because we’ve changed, not her. Swift — or at least the version of Swift on her albums — has remained largely the same person since her debut: a thin-skinned, bighearted obsessive, with a penchant for huge romantic moments. On her first five albums, her characters never eased into a relationship. Instead, they showed up at each other’s doors late at night and they kissed in the rain. An unworthy suitor wouldn’t just say something thoughtless; he’d skip a birthday party, or leave a teenage girl crying alone in a hotel room. (This aspect of her songwriting matured somewhat with the coming of the Joe Alwyn era, as the love stories got slightly more quotidian, but even those were filled with secret affairs begun in dark bars — a mite more dramatic than Netflix and chill.) Listen to her songs and you’ll ache at the resemblance to the most dramatic moments in your own private history. Listen to too many and you might ache again at the nagging feeling that those stories of yours have all been a bit uneventful and drab by comparison. What sort of real life can stand up against fantasies like these?
So, uh, I don’t recommend you listen to this list top to bottom.
But I do recommend sampling as many of these songs as you see fit. Even with the widespread critical embrace of poptimism — a development I suspect has as much to do with the economics of online media as it does with the shifting winds of taste — there are still those who see Swift as just another industry widget, a Miley or Katy with the tuner set to “girl with a guitar.” If this list does anything, I hope it convinces you that, underneath all the think pieces, exes, and feuds, she is one of our era’s great singer-songwriters. She may not have the raw vocal power of some of her competitors, but what she lacks in Mariah-level range she makes up for in versatility and personality. (A carpetbagger from the Pennsylvania suburbs, she became an expert code-switcher early in her career and never looked back.) And when it comes to writing instantly memorable pop songs, her only peers are a few anonymous Swedish guys, none of whom perform their own stuff. I count at least ten stone-cold classics in her discography. Others might see more. No matter how high your defenses, I guarantee you’ll find at least one that breaks them down.
Some ground rules: We’re ranking every Taylor Swift song that’s ever been released with her name on it — which means we must sadly leave out the unreleased 9/11 song “Didn’t They” as well as Nils Sjöberg’s “This Is What You Came For” — excluding tracks where Swift is merely “featured” (no one’s reading this list for B.o.B.’s “Both of Us”) but including a few duets where she gets an “and” credit. Songwriting is an important part of Swift’s spell book, so covers are treated more harshly than originals. Because Swift’s career began so young, we’re left in the awkward position of judging work done by a literal high schooler, which can feel at times like punching down. I’ll try to make slight allowances for age, reserving the harshest criticism for the songs written when Swift was an adult millionaire.
*This list was originally published in November 2017. It has been updated to include Swift’s subsequent releases. Additionally, some rankings have changed to reflect the author’s evolving taste. Like another famous Pennsylvanian, this is a living document.
“There’s a mistake that I see artists make when they’re on their fourth or fifth record, and they think innovation is more important than solid songwriting,” Swift told New York back in 2013. “The most terrible letdown as a listener for me is when I’m listening to a song and I see what they were trying to do.” To Swift’s credit, it took her six records to get to this point. On a conceptual level, the mission here is clear: After the Kim-Kanye feud made her the thinking person’s least-favorite pop star, this comeback single would be her grand heel turn. But the villain costume sits uneasily on Swift’s shoulders, and even worse, the songwriting just isn’t there. The verses are vacuous, the insults have no teeth, and just when the whole thing seems to be leading up to a gigantic redemptive chorus, suddenly pop! The air goes out of it and we’re left with a taunting Right Said Fred reference — the musical equivalent of pulling a Looney Tunes gag on the listener. Other Swift songs have clunkier rhymes, or worse production values, but none of them have such a gaping hole at the center. (I do dig the gleeful “Cuz she’s dead!” though.)
Swift has recorded plenty of covers in her career, and none are less essential than this 90-second rendition of the Rihanna hit recorded at the peak of the song’s popularity. It’s pure college-campus coffeehouse.
One of two originals on Swift’s early-career Christmas album, “Something More” is a plea to put the Christ back in Christmas. Or as she puts it: “What if happiness came in a cardboard box? / Then I think there is something we all forgot.” In the future, Swift would get better at holding onto some empathy when she was casting a critical eye at the silly things people care about; here, the vibe is judgmental in a way that will be familiar to anyone who’s ever reread their teenage diary.
A nasty little song that has not aged well. Whether a straightforward imitation of Avril Lavigne’s style or an early attempt at “Blank Space”–style self-satirization, the barbs never go beyond bratty. (As in “Look What You Made Me Do,” the revenge turns out to be the song itself, which feels hollow.) Best known now for the line about “the things she does on the mattress,” which I suspect has been cited in blog posts more times than the song itself has been listened to lately.