Let’s look at the closing chunk of Taylor Swift’s “Look What You Made Me Do” video. When all of the Old Taylors were falling like Valkyries, it made me realize how many different eras Swift has, and how each is its own self-contained thing. And from there, I had a thought: if you pitted all of Taylor Swift’s biggest songs against each other, which one comes out on top? What would a March Madness-style tournament of Swift’s biggest pre-Reputation hits look like? So, that’s what we’re going to find out today, but we need some parameters before we begin.
Qualifications: Only songs that are on Taylor Swift albums can participate, and since the Reputation era is ongoing, songs from it do not qualify. If “I Don’t Want to Live Forever” couldn’t hack it on a T.Swift record, it can’t hang with “Love Story” here. Nor do Taylor Swift features count, so we’re also nixing that song she did with B.o.B.
Metrics: Each match is going to be decided by which song has the stronger argument for it being better, and the impact of each song at the time, plus and its impact going forward. My personal taste matters, but it only as far as an argument can take it. And to keep things objective…
Seeding: Seeding and selection were done using Billboard’s list of Taylor Swift’s biggest hits. This way, I have zero input into the matches and seeding, but it also means we’re robbed of deeper cuts like “All Too Well,” “The Story of Us,” “Mean,” “I Wish You Would,” and “Haunted” that will have to play in the NIT of my heart. Going off Billboard’s list, here are our seedings.
- “Shake It Off”
- “You Belong With Me”
- “Blank Space
- “Love Story”
- “I Knew You Were Trouble.”
- “We Are Never Ever Getting Back Together”
- “Bad Blood (remix)”
- “Wildest Dreams”
- “Teardrops On My Guitar”
- “Our Song”
- “Back to December”
- “White Horse”
Round 1, Match 1: “Shake It Off” (#1, from 1989) vs. “Fifteen” (#16, from Fearless)
We’re off to a fiery Pop Taylor vs. Country Taylor start here in the first match. “Fifteen” is an almost storybook tale of what being in your freshman year of high school feels like, complete with making new friends and experiencing crushes. “Shake It Off,” meanwhile, is about Taylor Swift not just crossing over to pop, but leaving country in the dirt.
As far as song quality goes, it’s about a tie. “Shake It Off” has always been mindless but catchy, and “Fifteen” is the least essential of the Fearless singles because it feels like a rehash of what Swift did on her debut. It comes down to impact. “Fifteen” was a hit, but one that’s always existed in “Love Story” and “You Belong With Me”’s shadow, while “Shake It Off” still stands as Swift’s pop music coronation. It set the stage for her world dominating 1989 cycle, was the culmination of four albums’ worth of planning, and stuck the landing. “Shake It Off” advances in a blow out.
Round 1, Match 2: “Wildest Dreams” (#8, from 1989) vs. “Style” (#9, also from 1989)
After leading with one of our most lopsided pairings, the second match is probably the tournament’s most even coupling. “Style” and “Wildest Dreams” were 1989’s 3rd and 5th singles, and were the ones that were just kind of there, relatively speaking. Neither went to number 1 on the Hot 100 (“Style” peaked at 6, “Wildest Dreams” at 5), nor were their videos Earth-shattering events like “Shake It Off,” “Bad Blood,” or “Blank Space.”
These songs are both The Sexy One, so this match gets decided by which does that better. “Wildest Dreams” has more risque lyrics (“His hands are in my hair/his clothes are in the room”), but that pulsating beat and Swift’s delivery nail what being enraptured with someone is like, plus that “he’s got ____/I’m ____” chorus is Swiftian to its core. Were this tournament actual March Madness, this would be that game where no one expects much from either team, and then the winner hangs like, 35 extra points on the loser. “Style” advances in a rout.
Round 1, Match 3: “Love Story” (#4, from Fearless) vs. “Back to December” (#13, from Speak Now)
And so we come to our first county vs country throwdown of the tournament with “Love Story” from Swift’s 2008 breakout record Fearless squaring off against “Back to December” from its 2010 follow-up, Speak Now. The most interesting aspect of this match is that “Love Story” is one of Swift’s most mercenary singles, while “Back to December” comes from her least radio-friendly album. Not that Speak Now is radio-unfriendly–Lady Gaga’s Joanne was more obtuse–but within Taylor Swift’s oeuvre, it’s not artisan synth-pop, a country-pop smart-bomb, or a genre-hopper where every song could be The Single. Instead, Speak Now is her most writerly record; the one where she wrote almost everything solo and handled coproduction with longtime collaboration Nathan Chapman while refining what made a song a Taylor Swift song. You can hear her tease an idea out, play around with it, and move on once everything’s lyrically come full circle.
All this is to say that Speak Now makes for as solid as any Swift record as a whole, but tends to come up short on a song to song basis, let alone going against a song that goes for the pop jugular like “Love Story.” You could make an “artistry vs. commerce” argument here, but it’d rely on an even match. As is, “Love Story” is ruthlessly efficient, while “Back to December” just reminds me of Speak Now‘s lesser qualities: it’s overworked and too long. “Love Story” handily wins it.
Round 1, Match 4: “We Are Never Ever Getting Back Together” (#6, from Red) vs. “Teardrops on My Guitar” (#11, from Taylor Swift)
Here’s our first landmark match up! “We (eee!) Are Never Ever Getting Back Together” is, as I’m sure you know, Swift’s first overt move toward the CMA side door, while “Teardrops on My Guitar” was her first Top 20 hit. “WANEGBT” puts a lot on the board: it went platinum six times, was her first collaboration with pop braniac Max Martin, and was her first number 1 hit in America. The timely impact of this thing was damn high.
And yet, it’s going against “Teardrops On My Guitar,” which was the first song where all the parts of Taylor Swift clicked into place. The hyper-detailed lyrics, the melodramatic choruses, the feeling of being impossibly close to something and yet so far; these are the things that make up Swift’s best songs, and “Teardrops” is the first time they synergize. If we want to talk about impact, there’s little topping what’s essentially the flashpoint of her career.
Plus, “WANEGBT” hasn’t aged well. It made sense as a stopgap between country-pop Taylor and pop-pop Taylor, but seems contrived now that we’re through the looking glass. That, and it marks the birth of the “Taylor Swift Lead Single Obnoxious Spoken Word Bridge.” “Teardrops on My Guitar” advances.
Round 1, Match 5: “You Belong With Me” (#2, from Fearless) vs. “22” (#15, from Red)
A kind of quick aside: Red is Taylor Swift’s best record! It’s her most varied and overall strongest work: a 65 minute long player that has a little bit of everything, from pop collaborations to vintage Taylor Swift to her rockin’est songs. It’s solid enough that not even “featuring Ed Sheeran” showing up in the tracklist is an automatic KO. The hits outweigh the misses, and when things hit like they do on “All Too Well,” hooo boy, do they hit.
I praise Red because it gets bodied back to back in this tournament. Not that much would stand against “You Belong With Me,” which is still probably the Taylor Swift song in some circles for good reason, but “22” is especially not going to step to it. “You Belong With Me” is focused, catchy in a memorable way, and detailed while being relatable, while “22” has the focus-grouped blandness of a Disney Channel show that doesn’t get renewed after the first season. Swift gets called basic, sometimes to the point of unfairness, but “22” is fucking basic. “You Belong With Me” lights it up to advance.
Round 1, Match 6: “Bad Blood (Remix) feat. Kendrick Lamar” (#7, from 1989) vs. “Mine” (#10, from Speak Now)
If you listen to all the songs from Round 1 in one sitting, hearing Kendrick’s voice on “Bad Blood” is a blast of fresh air. Beyond that, “Bad Blood”’s remix has always felt secondary to its video, where Taylor Swift assembles a squad of impossibly beautiful women/pop stars whose sole purpose is to vanquish not-Katy Perry in a show of female solidarity and empowerment. The remix itself has always felt like it was slapped together by someone who knew what a remix was, but not how to make one; it’s just kind of dumb and loud.
In the other corner is “Mine,” Speak Now’s lead single. “Mine” is, in a word, deft: that opening “oh-oh-ooh-oh” and twangy guitar is surprisingly effective without clubbing you over the head with its own hookiness, and the pre-chorus is a great “Falling in slow motion” Taylor Swift moment (during the second time around, she laments “But we’ve got bills to pay” and her delivery always stuck with me). The song overall feels like a demilitarized zone between the picturesque stories of Fearless and the Here’s What Dating Famous People Is Like mindset of her immediately following work. “Bad Blood” might be bigger and get the assist, but “Mine” has the depth to win it.
Round 1, Match 7: “I Knew You Were Trouble.” (#5, from Red) vs. “Our Song” (#12, from Taylor Swift)
No disrespect to high school fairytale “Our Song,” but “I Knew You Were Trouble.” is 1. still a banger, 2. Red’s defining single, and 3. the literal GOAT.
“IKYWT” practically gets a bye.
Round 1, Match 8: “Blank Space” (#3, from 1989) vs. “White Horse” (#14, from Fearless)
Our final first rounder is a battle of deconstructions. “White Horse” functions as a grounding rod to Fearless’ fantastical highs, and reminds Swift that she’s not in Hollywood, but lives in a small town, and that the guy feeding her lines won’t be able to save her on his, well, on his white horse. The song counters the other Fearless singles, showing that for all the tiaras and stolen glances in school hallways, Swift understood that things didn’t always work out.
“Blank Space” is like that, but for Swift’s entire career. It takes the two most popular tropes of her songs: “Ours is a romance that will span centuries” and “I will salt your fucking fields after you wronged me” and sends them toward each other at ramming speed while claiming that yes, Taylor Swift will be that “crazy bitch.” It handily owns what people reduce Swift to, which goes far beyond “Maybe life isn’t a fairytale.” “Blank Space” goes to the next round.
Round 1 Winners: “Shake It Off,” “Style,” Love Story,” “Teardrops on My Guitar,” “You Belong With Me,” “Mine,” “I Knew You Were Trouble” “Blank Space”
Come back tomorrow to see how the tournament ends!