The Most Underrated Taylor Swift Songs

The Most Underrated

The Most Underrated is a meme in which I discuss the most underrated songs by an artist or band. Occasionally I may branch out, but this is the main theme. Today’s artist spotlight is on Taylor Swift!

I’ve been pretty open about my tumultuous relationship with Taylor Swift. We’ve been on the outs and on the ins. Or something. But one thing that has never changed is my appreciation for her music. The girl has got skills.

And, given Swift’s giant and far-reaching fanbase, I’ve become privy to which of her songs are the most popular. Therefore, I know which songs aren’t but should be. Today I’d like to talk about those songs. From throughout her decade-plus career, these are the Taylor Swift songs that deserve better.


  1. The Outside

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I wasn’t totally sure which song to pick from Swift’s debut, so I turned to the Swifties. The answer I kept getting was “The Outside” and so here we are. A song from Swift’s country-est of country days, it’s a difficult look inwards towards deep insecurities. We’ve all felt like outsiders at some point, and sometimes this feeling comes from people we used to trust.

Despite sounding fairly upbeat, this is a raw exposé of a lonely teenager. And, when I was a lonely teenager, this song meant a lot to me. I’m sure a lot of lonely teenagers could relate to this song, so it’s strange that it doesn’t get much love. Maybe instead it’s everyone’s secret vulnerability. Because we’ve all been on the outside looking in.


  1. Hey Stephen

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Even way back in 2009 when Fearless was released, I knew this song was the resident underrated gem. It’s so chill and mellow, Swift’s little “mmm, mmm, mmmms” like floating away on a cloud. What’s more, the song is just really cute.

It almost sounds nonchalant in how Swift proclaims her crush on Stephen. She “can’t help [herself],” but also doesn’t seem to mind if nothing comes of this. Yeah, she’s written a song about someone she doesn’t even know, but it’s more of an open flirtation than anything overwrought. And hey, that’s great in my book.


  1. Enchanted

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“Ren, are you just using this as an excuse to talk about this song?” How dare you ask me that. That is incredibly presumptuous of you.

But yeah, I am. “Enchanted” isn’t the most underrated song off Speak Now, but it still doesn’t get its due as Swift’s best song to date. It’s the other side of the “Hey Stephen” coin, an almost symphonic plea that this crush becomes something more. The bridge betrays Swift’s desperation as she pleas, “Please don’t be in love with someone else./Please don’t have somebody waiting on you.” And also, she wrote this masterpiece by herself. If that isn’t enchanting, I don’t know what is.


  1. Sad Beautiful Tragic

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Red as an album is sonically a mess, but it has some great songs. Many of those songs are lauded to this day, but strangely not this Lana Del Rey-esque track. It’s a haunting reflection on a doomed relationship, one that really gets under your skin.

This wasn’t a relationship where one party screwed over the other. They both were to blame for its inevitable collapse. It also contains this amazing lyric, “You’ve got your demons, and darling they all look like me.” Sad, beautiful, and tragic indeed.


  1. I Know Places

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I’m actually kind of baffled this 1989 track isn’t more popular. It manages to be both ominous and hopeful in the same song. However, the hopeful part (i.e. the chorus) is all about hiding and is in a minor key. This signifies that the hope really isn’t all that hopeful.

The thing that will inevitably doom the relationship is outside interference. People will judge and speculate, forgetting that Taylor and her lover are people too. “Loose lips sink ships all the damn time,” after all. Even though the relationship didn’t work out, this song has a special place in my heart.


  1. Dancing With Our Hands Tied

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This reputation track is basically a modern-day power ballad. Instead of guitars and drums, it uses synths and beat drops. It also describes a relationship as doomed as the ones in “Sad Beautiful Tragic” and “I Know Places.”

“I’m a mess, but I’m the mess that you wanted,” Swift proclaims on the second verse. Both Swift and her partner knew what they were getting into when they started a relationship, willfully ignoring all their misgivings. It really makes for an almost ambivalent regret. And so, I have no choice but to love this song. My hands are tied.


  1. Death by a Thousand Cuts

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I hesitate to call any song from Lover underrated, as the album just came out. But I really haven’t seen anyone talking about this song. That makes no sense to me, as this song is so catchy. It’s also inexplicable in the best way.

I mean, why else would I love the line, “I ask the traffic lights if it’ll be alright/They say, ‘I don’t know’”? And why does it make a strange sort of sense? I think it’s because of the sad acceptance Swift exudes in her voice. The relationship is over and it hurts. For that, this song gets a thousand applause.


Do you agree with my choices? What Taylor Swift songs do you think are underrated? Let me know in the comments!

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