Wednesday Listicles: Top Ten Taylor Swift Songs

Guys, we need to talk about Taylor Swift. It’s hard to believe, but she’s been with us for ten years now. Starting off as a country singer, she first found acclaim for albums like Taylor Swift and Fearless, before moving on to the pop genre with albums like Speak Now, Red and the world-conquering 1989. Since then, she’s been everywhere, inspiring debate amongst her most loyal fans and most staunch opponents. Some think she is God’s gift to the music industry. Some think she is a plague that has doomed us entirely. And some started out loving her ironically before they got in too deep and now they don’t know if their feelings for her are still ironic or have become genuine, like the ending to Inception. I’m firmly in that last category.

Look, Swift has made a fortune either singing hokey, terrible songs or blatantly copying the style of greater artists like Madonna (seriously, 1989 is just a more recent Madonna album. Listen to peak Madonna and that album back to back). However, she does, on occasion, display a gift for storytelling, and when she teams up with someone who actually understands music (looking at you, Jack Antonoff), then she can really get something going. So, in honor of Ten Years With T. Swizzie, here are the Top Ten Taylor Swift Songs.

As per usual, the ground rules: these are songs that are unequivocally, undeniably good. So basically, she has to actually be reaching for something with her lyrics, instead of just shouting “SHAKE SHAKE SHAKE SHAKE SHAKE” at the audience for four godless minutes. It also has to have something resembling musicality. So you won’t see too many of her earlier works on this list, where her voice is terrible and her guitar skills are mediocre. Examples of songs that don’t meet these requirements (i.e. bad songs we’ve been tricked into thinking are good) are “Love Story” (Good God, woman, your singing about how you’ll live forever like Romeo and Juliet do you not understand the stupidity of that sentence?), “Our Song” (everything wrong with Young Love songs or stories), and “Welcome to New York” (one of the worst songs I’ve ever heard). Meanwhile, there are some songs that aren’t necessarily masterpieces, but are entertaining nonetheless. So the cheesy Honorable Mentions include “Style,” “Mean,” “Enchanted,” and “Shake It Off.” Finally, a quick note. “You Belong With Me” is her most infamous song. It’s the one that won her acclaim, and also earned her the wrath of Kanyé West. It’s also the song that makes me wonder about my love for her. It’s not very good, and is overly simplistic, and yet I know most of the words by heart (ok, I know all the words by heart). However, despite my personal feelings, this song just isn’t good enough to make a list of legitimate talent. Therefore, it misses the cut. Now that that’s settled, let’s look at the list of songs proving that Ms. Swift just might have some talent after all.

10. “Mine”

Speak Now was Taylor’s first experiment at walking the line between pop and country. It is simultaneously her last country album and first pop album. And the best song on it was unequivocally “Mine.” Look, Taylor has better songs, and “Mine” can be kind of simplistic. But at its best, it’s just storytelling, like what Carrie Underwood became famous for. It’s a basic love story between a guarded young girl and her rebellious boyfriend. It shows that, despite a current trend of just writing poems about her ex-boyfriends, Tay-Tay also knows how to imagine a good relationship song. It’s a vast improvement over many of her earlier works (“Our Song” and “Love Story” spring to mind), and while it isn’t anything special, it does have a simple joy to it that makes it stand out amongst the first phase of her life.

9. “We Are Never Ever Getting Back Together”

Ok, I’ll admit it: this song was the beginning of the Taylor Swift that exists today-lovably awkward, always singing about some ex-boyfriend, and super poppy. However, there’s also one thing that stands out about this song: it’s something she has never done before, and hasn’t done since. The electronic-inspirations in the music, combined with Taylor’s angry release of emotions are mature in a way her other songs hadn’t been up to this point. She’s no longer the sweet, innocent lovelorn girl-she’s a woman who’s had her heart broken (way to go, Jake Gyllenhaal). And the spoken rant breakdown halfway through the song is brilliant, there’s no denying it. While Taylor has done better work since, this was the beginning of a new chapter, and it was impressive. Side note: this song would qualify for the top ten just for the line: “Listening to some indie record that’s much cooler than mine.”

8. “Wildest Dreams”

Look, 1989 is Swift’s greatest accomplishment to date. Combining talents with the man who wrote Britney Spears’ greatest hits, as well as some of the greatest working musicians, Taylor managed to turn the album into a musical achievement (before you chew my head off, no, it wasn’t better than To Pimp a Butterfly). Expect a lot of songs from it to make the list. Like this one, “Wildest Dreams.” Taylor tries out a bunch of different offshoots of pop on 1989, and one of them was to bring her voice down to a Lana Del Ray-esque key and belt out a dream pop masterpiece. Serving as a love ballad, it refers not to one of her past lovers, but a fictional (I assume) current lover, who she knows it won’t work out with, but she hopes will make for a memorable, if torrential, fling. It’s a bit out of her element, even if there’s nothing “new” about it (the themes themselves aren’t even unique to this album, as you’ll see further down the list), and that’s what makes it a unique and enjoyable experience. It’s not the best song off the album, but it is one of the more impressive hits in Swift’s repertoire.

7. “Tim McGraw”

Why does “Tim McGraw,” Taylor’s first song, work? Well, it’s because it isn’t necessarily a breakup song, even though it is. It’s a ballad about love the moment you realize it’s doomed. It’s like the teenage girl’s version of “I Will Always Love You” (which is actually a country song, despite Whitney Houston owning it always and forever). The fact the lyrics are young and yearning allow you to overlook the weakness in her young voice. And while it’s the most simplistic country melody you can get, it’s elevated by a unique balance of traditional country storytelling and the modern country twelve-string format, and combined with some very powerful lyrics for someone who wrote it as a seventeen year old. It has a specificity in its references that makes it stand out above your average pop or country song about love, making it feel unique, potent and even beautiful. It was an excellent sign of the best works that were yet to come.

6. “Clean”

This one is bound to be a little controversial. I mean, it’s not even one of the best-known songs on the album, let alone in her entire songbook. However, there’s something interesting about the idea of a Taylor Swift-Imogen Heap crossover. I mean, I can’t think of two different artists to team up. That’s like a crossover between the Marvel Cinematic Universe and Before Sunrise. But there’s something eerily poetic about Heap’s hypnotic beats and Taylor’s lyrics of love lost. Sure, it’s the most basic version of both of their works; however, the fact they made something like this actually work, and work well, is one of the most impressive accomplishments of not only this song, but the entirety of 1989.

Note: No version of “Clean” exists legally online, because Taylor is stingy about her music being shared. Listen to it on iTunes. Or don’t. That’s on her.

5. “I Knew You Were Trouble”

Similar to “We Are Never Getting Back Together,” “Trouble” is a musical experiment for Taylor. As Red served as her first foray into pop, she spent some time trying to find the style that suited her best. One of these styles she tried out was dubstep. Yep, dubstep. Written with Martin and Shellback (who are now members of her official team), it properly portrays the chaotic mood of Swift, who has been dated and left by yet another man in her quest for happiness, with the music jumping all over the place before finally erupting in her passionate, emotional release in the chorus. Unlike her previous songs about her ex-lovers, she focuses less on the actual details than she does on the emotional state of the relationship. Combined with the relatively fast pace of 154 beats per minute, the song is a unique, explosive experience that stands as one of Taylor’s best. Oh, and I’ll include the Goat version, Cage version, and Howard Dean version, because damn are those funny.

4. “Teardrops On My Guitar”

Yes, you knew it was coming. This was the song that made Taylor famous, and somewhat understandably. While I’ve been critical of Taylor’s whole “unrequited love” shtick that she had towards the beginning of the career (once a trope becomes that well-worn, it becomes a crutch). However, it actually works in “Teardrops,” and works well. Maybe it’s the fact she blatantly says “Drew” in the very first line of the song. Maybe it’s the fact that the simple acoustic guitar tune strips it of all pretense of falseness. Maybe it’s the fact that she never actually “gets” this Drew, and the ending of the song is the beginning, meaning her cycle of self-torture will continue to repeat itself. But there’s something beautiful about this honest, painful look at what cynics call the “friend zone.” While I can see people criticizing the simplicity of that guitar melody, or pointing out some of her worst traits that appear later in life, looked at as simply a standalone song, “Teardrops On My Guitar” is an excellent song. As a side note, why the hell do you stare at a picture of Drew all night, Taylor? That’s just unhealthy, girl.

3. “Out Of The Woods”

This is my favorite song on 1989. And had that god-awful music video not come along to forever taint it, it probably could have been #2 (I literally had to calm myself down that video made me so mad). However, as a stand-alone song, “Out Of The Woods” is one of Taylor’s best outings to date. Written with Jack Antonoff of fun., it’s a brilliant work of synthpop. It’s got this weird, catchy beat, as well as some of the best “this is secretly about my ex-boyfriend” work of her entire career. Drawing on her experiences dating Harry Styles, the song has a very ethereal feel, combining the instruments and beats of a 1980s song with the modern feel of a 2014 song (maybe even later…was Taylor Swift actually ahead of her time here?), and features some of Taylor’s best vocals to date. It’s also an emotional look at a relationship that may not have had the life it should have due to fears and anxieties making you rethink every decision you make. That’s actually a theme not often explored in the music industry, and I applaud Taylor for this level of honesty and foresight. Honestly, it’s such a brilliant song, it’s a shame that she made that music video and ruined everything. But that does open the door for the most famous song off that album…

Note: This music video is unwatchable. Just close your eyes and listen to the music.

2. “Blank Space”

Yet another song where I may actually know every word, there’s a good reason for that. This is such a brilliantly written song, you can’t help but remember it. Taylor made a name criticizing the men who have wronged her throughout her life, and I’m sure that some of them were scumbags. However, in “Blank Space,” she explores a concept that she hasn’t touched upon in any of her songs to date: that she herself may also have some blame in the breakup. She admits to her own jealousy, and her own self-sabotaging ways, in a way many artists never do in their songs. However, despite admitting that there’s a good chance that her next relationship may not work out, and he may treat her terribly, and she may overreact to things, she’s still open to love, and willing to give love a chance time and time again. Combined with an electropop beat that’s catchy and unique, this song proves Taylor’s talent at introspection, songwriting and storytelling. In other words, “Darling, [she’s] a nightmare dressed like a daydream.” (Such a great, great lyric)

1. “Fifteen”

I had no idea what songs would end up on this list starting out, but I knew one thing from the very beginning: “Fifteen” would be the #1 pick. By far, it is Taylor’s best song. In terms of lyrical writing, it’s her strongest outing. At its peak, country was about writing the truth of one’s life. Glenn Campbell, Merle Haggard, Kris Kristofferson and others made their name by singing the hard truths about their lives. That’s exactly what Swift does with “Fifteen,” except instead of the farm, or life on the road, or their battles with alcohol or drugs, Swift sings about being a fifteen year old girl in high school. And while that sounds simple or childish, it’s brutally and painfully honest, including tales of friendship, heartbreak, and the act of losing one’s virginity, as told from the point of view of both Taylor and her best friend Abigail. It is also elevated by the best work she has done musically and vocally. There’s something charming to the simple guitar strumming, harkening back to the days of the peak of country, before things became a cesspool of pandering and “Country boys and girls gettin’ down on the farm.” And while her voice still hasn’t matured by the time this song was released, it lends an air of honesty to the song that is desperately needed. Whether you love or hate Taylor Swift, this is the song that no one can deny, at least not honestly or intelligently, is a truly impressive piece of music.

At this point, I’m sure I’ve pissed enough people to start an argument by both Swifties and the anti-Taylor crowd, so I’ll sit back and let you express your own opinions. And if you have any mean things to say to me, know that I’m just gonna Shake It Off.


  • Anonymous Posted 11/02/2016 10:14 pm

    thumbs up, dude.

  • amo Posted 11/03/2016 7:05 pm


  • smart Posted 11/06/2016 12:21 am

    You did not just compare taylor swift to merle haggard

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