Top Twenty Taylor Swift Songs

What is it about Taylor Swift that has made her become arguably the biggest pop star of our time? Having watched a couple of her live shows I realized what made her stand out the most among her contemporaries. Taylor Swift is an artist that truly cares for and loves her fans and that love bleeds into her work. I hate using the word “real” to describe an artist’s approach to their craft but I honestly feel it’s an accurate way to describe her music. I’ll always say the best artists are those who are able to make a meaningful connection with their audience, no matter how famous they become. If there’s a beating heart behind the music there’ll always be something worth remembering.

But let’s put all of this sentimental talk aside and focus on the music itself because it is some of the best pop music has to offer. To celebrate the release of Swift’s latest record, the sweetly titled Lover, let’s look at the songs I’ve personally come to treasure from her.

20. “Starlight” – Red (2012)

This deep cut from Red is a sadly, near tragically underappreciated pop gem on a record that can be a little hit and miss on occasion. Beautifully catchy melodies that come hand in hand with romantic lyrics are just what Swift does best and why she’s one of my favourite pop artists of the decade.

19. “All You Had To Do Was Stay” – 1989 (2014)

I can remember the night I heard 1989 for the first time. At the time I was a self-labelled “hater” who went into the record expecting to hear something gross (if you were a teenager who loved punk and metalcore you couldn’t like something uncool like pop music, of course), however, “Out of the Woods” and this deep cut hit me in a way I never expected. This young emo had to swallow his pride and admit that I was thoroughly enjoying it. It was probably the best shameful moment I’ve ever had in my music fandom.

18. “Gorgeous” – Reputation (2017)

The cynicism by fans and non-fans alike towards this album, thanks to its still rather obnoxious lead single, was justified at the time. On the other hand, “Gorgeous” was a fun, peppy tune that gave me some reignited hope for the album. I didn’t realize it at the time but I think it came through on the promise.

17. “A Place In This World” – Taylor Swift (2006)

Swift’s eponymous debut is a record I’m still not awfully familiar with. During my initial listen the only song that stood out to me in any significant way is this one. I will give the record a more careful listen, I promise, but for now, I’m going to have this one on repeat.

16. “The Last Time” – Red (who am I kidding, you all know when these albums came out)

Another stunning deep cut from Red. I’m beginning to see a pattern here and I’m sure it’s only going to continue as we move along. “The Last Time” is the best duet Swift has ever performed. Gary Lightbody’s vocals are a perfect fit for its melancholic character.

15. “New Romantics” – 1989

A simple, endlessly fun bop of a song. What more can you ask of a pop song?

14. “Untouchable” – Fearless

I’ve recently come to believe that Fearless might just be Swift’s best album. It’s all so sweet, so endearing, so lovely. This song is a fine example of why this album deserves to be heard (and why the b-sides need more love).

13. “Getaway Car” – Reputation

Jack Antonoff has such a unique style in the songs he produces and “Getaway Car” is absolutely no exception. It’s a free-spirited, driving, and carefree gem of a song. This is what I love in pop music.

12. “We Are Never Getting Back Together” – Red

We’re out of Red’s deep end now and into the tunes everyone recognizes whether they’re fans of her or not. How can I complain about this track’s popularity when it’s just so ridiculously fun? “You go talk to your friends, talk to my friends, talk to me!” 

11. “You Belong With Me” – Fearless

Why not mention another notable hit? I never paid much attention to this song, thinking it was a generically simple, cheesy love song. It is that, but once again, Swift knows how to write a brilliant chorus. And that twist at the end of the music vid gets me every time. I love it.

10. “Sparks Fly” – Speak Now

The first song from Speak Now lands at number ten. That not only speaks to the quality of that record but also of its numerous highlights. Speak Now was the second record I heard from Swift after loving 1989 and this song clicked immediately. But unlike many other songs that do so, this hasn’t grown off of me in the least.

9. “22” – Red

Some of the best pop songs are those that have more sugar than a krispy-cream doughnut. I say some because not everyone can pull it off well. Swift is one of the artists that do. “22” is a jam ripe for summer.

8. “The Way I Loved You” – Fearless

If there has been one thing apparent from this list it’s that Swift is in no way a “singles” artist. Her records harbour so many superb deep cuts and “The Way I Loved You” might be the best of them. I cannot say enough good things about the chorus here. It just rocks.

7. “Delicate” – Reputation

This pulsating, beautiful, and earnest pop song is Reputation’s best moment and an undeniable top ten song in Swift’s discography. I can picture the lit-up skyscrapers passing by the car window as this plays in the background.

6. “Long Live” – Speak Now

Speak Now closes in the best way possible. I won’t pretend that this doesn’t play out like a signature classic from a Disney film because in what world would that ever be considered a bad thing?

5. “Enchanted” – Speak Now

Speak Now is home to so many of Swift’s best songs and “Enchanted” is nothing short of lovely. Absolutely lovely.

4. “Out of the Woods” – 1989

The song that turned me from a hater to a lover (pun intended!). This is an obvious top five-song, there’s no dispute. The chorus is one of the best uses of a repetitive hook I’ve ever heard and the choral vocals that rise up in the mix during the bridge and its final moments are euphoric.

3. “All Too Well” – Red

The consensus would probably argue that “All Too Well” is the best song Swift has ever written. I would honestly agree, even if it’s not my personal pick for the number one slot (and these lists are always personal). It’s among the saddest songs she’s written to date and the emotion is definitely palatable. It’s the definition of a perfect ballad.

2. “Style” – 1989

All of my rough drafts had this song at the top spot but then my heart got in the way and we had a bit of a debate. Eventually, the heart won. If “All Too Well” was the perfect ballad, this is the perfect pop song. Everything about it is what I love in pop music, the romantic and somewhat sensual lyrics and pulsating, driving synths and nightlife aesthetic.

And now A Diverse Sound’s personal pick for the best Taylor Swift song is….

1. “Love Song” – Fearless

If the video for “You Belong To Me” made me tear up a little you can imagine how I felt for this one. This song became my biggest fantasy for the longest time. Meeting a girl at a ball, getting to dance with her, and falling in love? That was the dream. I had a couple of chances where this could have become a reality but alas those times were not to be (and probably for the better because I was not ready for a relationship at all back then). I still listen to this and dream about what could be in the future because when it comes down to it I’m a guy with a mushy heart who lives for this stuff. The song is a pop classic and I think we would all agree.

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