Frankly, I expected to publish my top 100 albums of the 2010s feature on this website and then mostly leave it alone for a while. But boredom during this pandemic has given way to a few additional features. There’s my top 50 albums of the ’90s, ’00s, and ’10s, but mostly it’s been a love for Twitter polls giving way to an urge to inject my own opinion. My top 25 Kanye West songs, my top 25 Beatles songs, yadda yadda. It’s not the most thrilling content, but whatever gets me writing.
Taylor Swift’s bracket came third, and wouldn’t you know it, “Blank Space” torched through all competition, and now it’s time for me to make my own list. Moreso than with Kanye West and The Beatles, 25 proved to be an uncomfortable cutoff, not necessarily because she has more great songs than The Beatles, but because the quality of so many of them bunches up around number twenty-five. So with specific apologies to “Clean” and “Getaway Car,” these were the 25 that I felt married to, and I wouldn’t want to leave a single one off a playlist of Taylor Swift essentials.
I got on the train later than I’d like, but since falling in love with Red, I’ve grown to regard Taylor Swift as one of the very most important recording artists of the past fifteen years. In that short time, she’s built an incredibly formidable library that can rival that of nearly anyone. Here’s the cream of the crop.
25. “Paper Rings”
Taylor has several indulgently “fun” songs, but “Paper Rings” is by far the most successful.
Shout outs to the guy absolutely losing himself in the “ONE, TWO, ONE TWO THREE FOU–“
This isn’t exactly my wheelhouse, but no song is as emblematic of why Taylor Swift caught fire, which is that her music was absolutely indispensable to young girls. “Fifteen” is an unflinching look into young womanhood, the forces that wish to do it harm, and – “we both cried!” – the importance of camaraderie therein.
23. “Love Story”
But she was just as important to five-year-olds as she was to fifteen-year-olds. This song might not be on this list if it wasn’t for its key change selling its narrative’s dramatic finish.
Her breakthrough album’s most expert production serves one of its most expert uses of dramatic imagery.
21. “The Story Of Us”
“The Story Of Us” is rather minor writing-wise, but the frantic drums, the urgent guitars, and the tumbling piano result in one of the finest productions of her career.
20. “All You Had To Do Was Stay”
The way that repeated, falsetto “stay” beams through and through is just gorgeous.
19. “State Of Grace”
It was unreal to hear a Taylor Swift album open with those booming drums. She was no stranger to grandeur by this time, but still, “State Of Grace” gestured toward something more eternal.
18. “I Wish You Would”
1989 had a flawless blueprint for pop most notable for its layered use of Taylor’s voice, never more apparent than in the distant, booming “I WISH YOU WOULD!” or the little, “I, I, I, I, I, I wish I wish I.”
17. “I Knew You Were Trouble”
Yes, the drop. By this point, Taylor’s pop turn felt inevitable, and on paper this sounds like it’s forcing things. But despite 2012’s attitudes towards dubstep, this is one of her most flawlessly executed refrains. Now freed of its baggage, it sounds natural.
16. “Picture To Burn”
No Taylor song feels as kinetic and chaotic as “Picture To Burn.” It’s haunted by an uncertainty about where exactly her rage will be directed.
The way “Red” echoes and the voice – “reh-eh-eh-ed” – reverberates is stunning, and she gives this song one of her best vocal performances.
14. “Begin Again”
Taylor Swift’s most narratively satisfying moment puts a bow on the pre-pop portion of her career. And then we watched it begin again.
13. “Hey Stephen”
Every single time I listen to this, I’m in awe of how meticulously handled the rhythm of each syllable is.
12. “Forever & Always”
Her most underheralded song? “Forever & Always” is not Taylor Swift’s best breakup song, but it’s her most forceful and focused. She’s released many songs with the intent of humiliating its subject, but here she’s so surgical, so methodical. Target destroyed.
11. “Cruel Summer”
Produced and co-written by Annie Clark, “Cruel Summer” is a peculiar entry in the Swift canon, but it’s perfect pop, especially the bridge. I would very much have liked Lover‘s rollout to start with this.
Had “All Too Well” not happened, it’s very possible that “Enchanted” would be discussed as the sorta-secret masterpiece in Taylor Swift’s discography, the apotheosis of the fairy tale themes from her earlier work that would mostly vanish hereafter.
Man, when she gets to “please don’t be in love with someone else.”
Not many songs on this list could be called understated, but despite coming from her brashest album, here’s “Delicate,” the moment where Taylor Swift best meshed with Reputation‘s aggressive embrace of 2017’s popular music. On it, she hesitates, anxious and worried: “Is it too soon to do this yet?/Cuz I know that it’s delicate.” Then: metronomic isn’t its.
8. “Holy Ground”
It chugs along as her most efficient composition and builds to something wonderful, but what really sells it are the narrative turns. That was the first day? It fell apart in the usual way, you guess?
7. “We Are Never Ever Getting Back Together”
The moment she turned from household name to planet eater.
Around 2014, the final stragglers were rounded up to accept Taylor Swift’s canonization, and songs as cool as “Style” – its badass riff accompanying the verse – went a long way in finally closing the book on that case.
5. “The Best Day”
Absolute tear-jerker. Please go read Keith Harris’ article about how Taylor Swift and Kanye West wrote the 21st century’s two greatest songs about mothers.
4. “Sparks Fly”
Speak Now‘s infatuation with electric guitar comes out best in this immortal guitar riff. Musically, her career’s strongest moment.
3. “Blank Space”
The success of this treatise on her public image felt so good that she felt emboldened to make the “Bad Blood” music video.
2. “All Too Well”
Her epic. “All Too Well” never lets up, suffocating you with a sense of true romantic loss, through tee ball teams, refrigerator light, and, yes, Chekhov’s scarf.
1. “You Belong With Me”
Her breakthrough. Musically so light on its feet, spiritually closer to Simple Plan than the nearest country artist. Not a song valorizing unrequited love so much as a tragedy about the folly of believing that anybody “belongs” with anyone.