Top Ten Taylor Swift Songs (2019 Update)

On the eve of a new Taylor Swift album, I thought I would make an updated list of my top ten Taylor songs. My last list was made right before Red, which turned out to be her best album, so it was a list that desperately needed updating. It’s crazy to think how long I’ve been listening to Taylor . . . it was twelve years ago and she’s been a part of my daily rotation ever since. I remember going to Borders early in the morning to buy Fearless on release day. Counting down the minutes to midnight to buy Red on iTunes. Watching the DVD of the Speak Now tour on Christmas day. It seems like just the other day she made a song about being 15 and now she’s about to turn 30. As long as she’s creating new music, I know I’m in. I have little doubt she’ll continue to make music I find valuable, as evidenced by this list, which contains songs from every era of her career. Here’s to another twelve years and more, Taylor. And now the list:

10. Today Was a Fairytale

As far as I’m concerned, this is the apotheosis of her “storybook love” phase, even more than “Love Story,” which is a little too fanciful to hit home. This is a more down-to-earth version of that youthful sentiment, and we real fans will always chose down-to-earth Taylor over her other personas.

9. Holy Ground

The closest she got to something resembling the “indie band” music she playfully derided in the lead single off Red, showing off her ability to make different kinds of music in her inimitably listenable style. (See also “I’m Only Me When I’m With You”)

8. Delicate

I thought this song was the best thing on Reputation after one or two listens of the album and I was so glad it turned into a massive hit. The song is (dare I say) really delicate, a highwire act in terms of both Taylor’s voice (which is at her most ethereal) and having the beats coming in at just the right time and intensity, so as not to disrupt the fragile mood she sets at the beginning of the song.

7. Shake It Off

The best lead single of any Taylor album by far. Instantly infectious, it will continue to shake butts for decades to come.

6. Last Kiss

Still a masterclass in pop lyricism. “How you kissed me when I was in the middle of saying something, there’s not a day I don’t miss those rude interruptions”; “All that I know is I don’t know how to be something you miss”—she wouldn’t top these lines until the number one song on this list.

5. Enchanted

If she has a “November Rain,” this is it. A nearly 6-minute ode to that love-at-first-sight yearning, it features a stylistically shifting interlude 75% in that just amps up the emotion to another level. Grand and sweeping, hopelessly romantic, a classic.

4. State of Grace

Taylor lyrics cascading over a big arena rock sound is something to behold. One of the best album openers of all time.

3. Our Song

The original. I’ll always have a fondness for this song, the song that made me fall in love with her music, the song I listened to over and over, my pop song “Infinite Jest.”

2. Begin Again

A perfectly written song. A perfect blend of story and emotion. Every beat is delivered at just the right time in just the right way. Deceptively simple, but powerful and hopeful.

1. All Too Well

Her songwriting masterpiece. She takes you through a relationship from beginning to end, using the most exquisite lines she’s ever come up with. “You call me up again just to break me like a promise, so casually cruel in the name of being honest.” Jaw-droppingly good. The song feels big, important. It crescendos in a way that soars, delivering you to that blissful place that all great songs take you. It’s amazing art, there’s no other way to put it.