Here are the results of Round 1.
Let’s being Round 2!
Round 2, Match 1: “Shake It Off” (#1, from 1989) vs. “Style” (#9, also from 1989)
Twenty years from now, when Teen Jeopardy! needs a $400 answer in “Finish the Lyrics,” that sucker’s going to read: “This 2014 song cautions that ‘The haters gonna hate, hate hate/And the fakers are gonna fake, fake, fake’” and some nervous kid with too much hair is gonna say “What is ‘Shake It Off’?” while sucking spit out of their retainer. “Shake It Off” is guaranteed to be at least one of Swift’s two most enduring songs, and for an artist as careerist as she is, that gives it no small amount of weight. I remember seeing the video for the first time, and recognizing how it grabbed from different aesthetics, uniting them all under Swift. The intent was clear: Taylor Swift was making pop, and she was making pop for everyone.
And yet, “Shake It Off” is limited in its pull for everyone; it’s a song that could be sung by anyone. “Style” keeps all the pop trappings in that pulsating beat, the synthetic kick drum, and that soaring chorus, but there’s also real poignancy in the lyrics, too. It’s both a pop creation and a Taylor Swift creation. I realize that I’m talking about a single from what’ll be a defining mainstream pop album of the 2010s, but it feels like this song didn’t chart high enough. “Style” prevails in the upset to go to the Final Four.
Round 2, Match 2: “Love Story” (#4, from Fearless) vs. “Teardrops on My Guitar” (#11, from Taylor Swift)
Even though it’s only an 11th seed here, “Teardrops” is Swift’s biggest hit from her self-titled, making this the oldest possible Country Taylor match. And “Teardrops” handily wins, because “Love Story,” while a great radio single, retrospectively lives all the way under “You Belong With Me.” Plus, not that my opinion sways a lot here, but “Teardrops on My Guitar” kicked off my favorite Taylor Swift sub-genre: helplessly watching everything pass you by (see also: “The Story of Us,” “I Wish You Would”). “Teardrops” makes the Final Four.
Round 2, Match 3: “You Belong With Me” (#2, from Fearless) vs. “Mine” (#10, from Speak Now)
A few paragraphs ago, I said that “Shake It Off” was guaranteed to be one of Swift’s two most enduring songs. Its counterpart is “You Belong With Me,” an absolute monster of a song that has serious pathos in addition to being one of Swift’s catchiest hits (just try not to singalong to “So why can’t you see-eeeee-eee?”). “Mine” could maybe chase down a win against any of the other Fearless singles, but “You Belong With Me” is just too solid and quintessentially Swift to lose. To invoke another March Madness archetype, this is that game where the unassuming low-seed that clawed its way this far gets tossed into the sun. “You Belong With Me” belongs in the Final Four.
Round 2, Match 4: “I Knew You Were Trouble.” (#5, from Red) vs. “Blank Space” (#3, from 1989)
The second round ends with a clash of the titans. Both “I Knew You Were Trouble.” and “Blank Space” were their respective albums’ flagship singles: not the leads, but the ones that eventually defined the era. “I Knew You Were Trouble.” proved that Swift could hijack a contemporary trend for her own end. This marked a departure from “We Are Never Ever Getting Back Together,” which was fairly down the middle as far as radio sounds went; the only risk involved was that it wasn’t even country in passing. But CMA sweetheart Taylor Swift throwing dubstep drops into a single? That easily could have backfired.
Okay, so as I’ve mentioned before, I don’t really like “Blank Space,” but even I remember thinking, “Yeah, this is happening” when it started taking off in late 2014. “Shake It Off” might have broken the ice for Swift’s “first official documented pop album,” but “Blank Space” was what proved that she had pop staying power. It quickly eclipsed “Shake It Off”’s stint at the top of the charts, and solidified her arrival at pop’s center. “Blank Space” also marked, somehow, a new high in Swift’s popularity since it and its whip-smart video didn’t just look at Taylor Swift, Actual Person, but confronted Taylor Swift, Media Construction, blurring the two into one, self-aware reflection (if you squint, this is also where the road to Reputation begins). A few dubstep drops ain’t got nothing on that, as “Blank Space” rounds out the Final Four.
Final Four: “Style” (#9), “Teardrops On My Guitar” (#11), “You Belong With Me” (#2), “Blank Space” (#3)
Round 3, Match 1: “Style” (#9, from 1989) vs. “Teardrops On My Guitar” (#11)
And so one Cinderella run has to come to an end, but which?
“Teardrops On My Guitar” got here by being one of Swift’s best bedrock songs, while “Style” is exemplary of her, well, style. It’s a match of potential vs. actualization. “Teardrops” is great, but it’s limited by the fact that Swift is still figuring things out; it has all the right pieces, but isn’t quite realized. “Style” has a confidence and grace that’s missing from “Teardrops,” and just about every aspect of the former lives in bolder color than the latter. The instrumentation is richer, the lyrics are more complex, and it’s like night and day with Swift’s vocals between the two (it’s those swells at the end that really put it over the edge); in terms of composition, it’s hard to argue against “Style.” And the pair almost exist on a continuum: “Style” might be the cooler, older version of who she was on “Teardrops,” but both get denied because of some impossible to know other girl who almost pushes them into breaking. I think that kind of continuity is neat. “Style” is one of Taylor Swift’s best hits.
Round 3, Match 2: “You Belong With Me” (#2, from Fearless) vs. “Blank Space” (#3, from 1989)
Our first round 3 match was a battle of the underdogs, so of course, the other match is a tussle between dominant 2nd and 3rd seeds.
Let’s change our approach for a second and consider a hypothetical. Let’s say Taylor Swift isn’t Taylor Swift. Let’s say her career’s the same through Fearless or Speak Now, but the whole VMA debacle never happens, so she’s never thrown into a national pop culture controversy, so she remains a very successful country artist, but not someone whose profile reaches the point where Taylor Lautner tries spin-kicking the head off of Kanye West mannequin twice while defending her honor in an SNL monologue before settling for a measly punch (this is one of those sentences that sounds made up, but I swear to God it isn’t). And, let’s say that she never tries the pivot on Red, more or less sticking to country. She’s still noteworthy, but falls into a holding pattern after Speak Now where she notches a mid-tier crossover hit or two per album that gets bounced by the newest Selena Gomez or Imagine Dragons single.
In this hypothetical, “You Belong With Me” remains her commercial high-point, and eventually gets a “We Need to Talk About Taylor Swift’s ‘You Belong With Me’” gif-heavy piece in Buzzfeed in 2018 because that song’s a success no matter where you place it. Even if Swift never did anything else, “You Belong With Me” endures because it immediately zaps everyone who hears it back to some personal memory they have with either the song or the situation described therein.
On the other side, “Blank Space” is still a creative and commercial achievement, but everything great about it hinges on Taylor Swift being Taylor Swift. It’s too dependent on context to reach that topmost level, and truth be told, Swift is at her most hit and miss when the songwriting relies too much on Max Martin’s melodic math. “You Belong With Me” is less sculpted, but more enthusiastic, altogether better, and in fact, “You Belong With Me” is one of Taylor Swift’s best songs.
FINAL ROUND: “Style” (#9, from 1989) vs. “You Belong With Me” (#2, from Fearless)
Alright, main event time. In one corner, we have a quietly impeccable synth-pop tune from 1989 which has toppled that record’s biggest single, and KO’d one of Swift’s earliest hits to get to the final. Against that is a song that could be said encapsulates Swift’s artistic essence during her country days, and quite possibly her most famous creation.
“Style” is the sturdier of the two, but “You Belong With Me” is Swift’s best earworm, so it’s musically a draw, and “You Belong With Me” runs laps around 1989’s least successful hit on every commercial and impactful level. That gives it an edge going into the final question: which song just does more?
And that’s where “Style” shines. “You Belong With Me” is universal, yes, but that’s because daydreams are. The phrase “you belong with me” is a thing you say when there is exactly a 0% chance of you two getting together, and the song cops to that; the lyric “Dreaming about the day” is arguably the quietest part of the song, but it’s still there. It’s a daydream content to be a daydream. Meanwhile, “Style” describes a complicated “will it work, or won’t it?” Swift has with a guy where everything they do gets tangled up–both sides admit they’ve been with someone else, but they keep coming back for each other because they just feel so good together.
But it’s not that simple, right? No one gets as invested as Swift is on “Style” over something that just works because it’s fun: it could be that you two stay together because it’s easy, or because you like the rush, or way you make each other feel in spite of all the baggage that comes along. Yet the song chooses to believe that it all works because of James Dean eyes and classic red lips. That’s every bit as fictional as “You Belong With Me,” but “Style” knows that. It knows that it’s grasping onto superficial reasons to avoid hard questions and the fallout of crashing down, and because of that, “Style” wants itself to be real more than anyone else. It knows what longing and–this is important–loss feel like, but it also knows that picturesque love stories don’t always work, which is why it desperately wants to believe that this supercut of romance can be true just once. “Style” goes in several directions, and is compelling in each one, so “Style” is Taylor Swift’s best song.
Ranting Research Notes
-That “with some indie record that’s much cooler than mine” lyric in “We Are Never Ever Getting Back Together” lands a whole lot different now, considering how concerned with “cool” Swift’s next two records would be.
-It took doing this tournament for me to realize that “Our Song” and “Love Story” aren’t just the same song.
-Did anyone lose in the Twilight series as hard as Taylor Lautner?
-Speaking of Lautner: could you imagine what would happen if Swift ever got “Kanye in ’09” level backlash? She made Reputation after like, half a week of Twitter jokes; I think she just kills everybody if the backlash ever goes that far.
-A note on the pros and cons of song selection/seeding methodology: I wanted to use something objective, and considered a few different methods to keep things equal, but any number-based system was going to favor “22” at the expense of like, “Tim McGraw.” I went with Billboard in the end because their chart contains the least amount of weirdness–there’s no differentiating between pop versions and deluxe versions and such, nor would the earlier songs be at disadvantage because of being uploaded to Vevo years after their release. That said, Billboard still wasn’t perfect, since video performance was included and likely boosted some songs (looking at you, “Bad Blood”), and wasn’t present for others (“You Belong With Me”). Still, though, for someone as invested in cultural dominance as Swift, it got the job done.
-Yes, I’m reviewing Reputation, and soon.