Guest Post: A Ranking of Taylor Swift’s Best Songs, Part 1

My friend Jon asked to guest post at Accidental Shelf-Browsing as his own blog is basically defunct; what he wanted to publish was his Top 10 ranking of Taylor Swift songs. This is considerably off-brand for this space (perhaps I am a fool for worrying about such things, but I do), so I said I would be interested in something that was very reflective about the aesthetic standards by which he made his judgements; I keep meaning to write a post about aesthetic standards and choosing between them, which his piece would then complement. The following is what he gave me. The usual disclaimers apply: Jon’s opinions do not represent my own, nor do I take responsibility for them. The only changes I have made are in converting formatting to something compatible with WordPress and in light copy editing.

Taylor Swift Speak Now - Pittsburgh

“Taylor Swift Speak Now – Pittsburgh,” by Ronald Woan. Source:

Because of its length, his post will come in two parts, which I have split arbitrarily in the approximate middle. This is Part 1.

An Objective and Unbiased Ranking of Taylor Swift’s Best Songs

Jon Wong

A Primer:

In 2009, when I first began listening to Taylor Swift (to the extent that listened to all pop music), I felt a certain reluctance towards calling myself a “fan” of hers. Part of this was, I admit, due to my own musical bias/elitism regarding pop music—I enjoyed pop music as a collective, but I believed that pop music, by nature of its appeal to the masses, was inherently vapid, certainly in production and delivery, if not in actual content. Taylor Swift, along with Katy Perry, Lady Gaga, Rihanna, and the rest of the biggest and best of the late 2000s, felt very much like guilty pleasures. They were guilty pleasures I embraced and talked about openly, but guilty pleasures nonetheless. I felt the same way about Sum 41, Green Day, Avril Lavigne, Simple Plan, Linkin Park, and the rest of the pop-punk bands that came before them in the mid-2000s. I was also an idiot.

Which is not to say that I was wrong about pop music consisting primarily of pre-packaged production and delivery. But I was perhaps wrong about my indictment of those qualities as being (a) inherently bad, and (b) an indicator of artistic dishonesty. Either way, Taylor Swift came up in discussion back then primarily as a point of contention between my friends who disliked country music and my friends who were country music fans. Oddly enough, she was hated by the former for being too country, and hated by the latter for not being country enough. Haters gonna hate, as Taylor Swift herself would say in future years.

Then Kanye West did his whole shtick at the VMAs (you know, the one where he interrupts her acceptance speech for winning the Best Female Video award), and I immediately felt a very strong sympathy towards Taylor Swift. It wasn’t just about Kanye West being a jackass, which, of course he was (and still is? I don’t know what he’s like these days). That incident resonated with me on a fundamental level because it sort of summarized the general sentiment around what it was like to be successful as a female artist. You couldn’t just be a great artist and be recognized/celebrated as such. If you weren’t a controversy, the world would find a reason to turn you into one. And if you didn’t give them enough ammunition to do that, some guy would do it for you (to you?) like a half-cocked gun (if you’ll excuse the pun).

So, almost as a protest against how the world was treating her, I insisted on treating Taylor Swift like a “real artist”. It helped that I began to realize that her music was good. And the more I listened to her music, the more I realized how good of a lyricist she is. And how much I enjoyed the sentiments behind many of her songs. Her struggle with her relationship to the term “feminism” (due, I’m relatively sure, to her background as a country singer) mirrored my own struggle with the term as we both seemed to come to the understanding that whatever hang-ups we had about what the term represented, not identifying as one did far more harm than good.

More than anything, this post was inspired by the simple realization I had the other day that there are very few pop artists who have written more than ten songs that I genuinely enjoy. Off the top of my head, I rattled off at least 15 songs that could be consideration for a top 10 list, and by the time I went through her discography and made a list, I was 18 songs deep. So I began to consider a methodology for whittling them down.

In baseball, scouting grades exist on a 20-80 scale, 20 being bottom of the barrel, and 80 being top-shelf. Position players are rated using 5 tools: hitting, power, speed, fielding, and throwing. I’ve always thought this kind of methodology might translate, in some capacity, to grading music, so when looking at Taylor Swift’s best songs, I will rate them according to 5 tools: song catchiness, show-stopping capabilities, lyrical content, lyrical quality, and je-ne-sais-quois.

Song Catchiness: Perhaps the most subjective, but easiest to rate, song catchiness is kind of self explanatory. Pop music as a category tends to fare pretty well on this scale by nature. Most things that make it to top 40 radio are at least a 50 (average) on the 20-80 scale. I kinda feel like Mirrors by Justin Timberlake is maybe a 40? It’s hard to think of examples of a 20 in pop music. I mean, I think most of Drake’s stuff fares pretty poorly on the song catchiness scale, but he’s still uber popular so what do I know? On the flip side, Carly Rae Jepsen’s Call Me Maybe is an 80.

Show-stopping capabilities: The other scale (on a musical level) that separates catchy songs from great songs. Show-stopping capabilities (for lack of a better term), refers to a song’s ability to really make you “feel” the music, if you know what I mean. Songs at the top end of the range tend to be songs that are either openers or closers at concerts, or they’re the first or last track of an album. Lady Gaga’s Paparazzi is an example of a song that I’ve always thought rated highly on the song catchiness scale (like a 65/70), but is like a 35/40 on the show-stopping scale. It’s hard to picture anyone choosing to end a Gaga concert with Paprazzi. I would put most of Coldplay’s discography on the low end of the show-stopping scale, with the exception of Fix You, which is probably why it’s their best song.

Lyrical content: What the theme or message of the song is. Not all songs that aren’t about love score poorly on this scale, but I mean, have you listened to the Owl City song about going to the dentist (I think it’s called Dental Care)? No? Maybe it’s because no one thinks going to the dentist is something remotely worth writing a song about. That’s like a 20 on the 20-80 scale. On a related note, though, not all songs about love score high on the lyrical content. I’ve talked once with a friend about how Bruno Mars’s song Grenade is like a 35. Songs that tell stories tend to rate pretty well on the scale. Songs that score below 50 tend to make me roll my eyes. Sometimes, I have a hard time deciding how I feel about songs that are like a 70/80 on song catchiness and show-stopping capabilities, but are a 50/55 on the lyrical content scale (looking at you, Camilla Cabello’s Never Be the Same).

Lyrical quality: You can write lyrics that tell a story/message that is totally worth writing (70/80 on the lyrical content scale), but if you aren’t a particularly good lyricist, you might fall flat here. Conversely, you can write a really good line, i.e. Young Money’s Bedrock: “Call me Mr. Flintstone, I can make your bed rock” (which come on, that’s hilarious), buried within a song that’s like a 40 on the lyrical content scale (see again: Bedrock). Nickleback famously penned the song that always comes to mind when I think of scoring a 20 in this category: “I like your pants around your feet,” is the first line of Figured You Out, and it only gets worse from there. Come to think of it, that song might be a 20 on the lyrical content scale too. Good job Chad Kroeger.

Je ne sais quoi: This last category encompasses everything else, like age of the artist (which sometimes matters), the song’s place in the album (which sometimes matters), whether or not the song title is also the title of the album (which sometimes matters), etc. Basically, it’s all the stuff that doesn’t always matter until it does. I originally thought of calling this category “brownie points,” but I feel like that devalues the contributions of some of these factors when they’re sometimes quite significant. Either way, I’ll mention this category as it becomes relevant in the rankings.

Finally, it is worth noting that not all these categories are weighted the same. In baseball, the “hit” tool is more important than the “speed” tool because inasmuch as they are discrete categories that contribute to a player’s value, it is more important to be able to hit a baseball than it is to run fast. Running fast helps, but running slow won’t kill you. But you can’t not hit and still play baseball. By the same token, lyrical content is more important than show-stopping capabilities, for example. It helps if a song can bring down the house, but it doesn’t have to do so to be good. It’s much harder for a song to be good if the contents of its lyrics aren’t worth hearing. That being said, let’s begin with some honorable mentions.

Songs that are stupidly catchy: 22, You Belong With Me, Shake it Off, Forever and Always

These songs made the short list because they’re like an 80 on the catchiness scale and at least a 45/50 everywhere else. 22 makes me chuckle because you can hear the Max Martin influence (if you’re not sure what that is, you can hear it in All You Had To Do Was Stay and How You Get the Girl too). Taylor Swift has written a number of other you’re-with-some-other-girl-but-you-should-really-be-with-me songs, but You Belong With Me was the first of that category that really became a big hit (due in large part to the aforementioned catchiness). It’s hard to know what Taylor Swift’s most famous single will be when all is done, but I suspect that Shake It Off might end up being the one single that she’s remembered by. Finally, Forever and Always never ended up being released as a single, but aside from being super catchy, I’ve always appreciated how it simultaneously underscores and undermines the idea of great songs being a vehicle through which we are allowed to express sentiments that would otherwise scare us a little if it weren’t for the fact that they were song lyrics.

The weird one with no category: Never Grow Up

I don’t know why I didn’t hesitate to put this song the short list. I guess it’s because it’s well written, and there’s a certain sentimentality to remembering what it’s like to grow up? I don’t know. I don’t usually go for songs written by adults about how they wished their kids could remain kids forever. Aside from being impractical, it also sounds like the kind of thing you would say if you were a parent and wanted to make your kid’s childhood all about you. I mean, that’s not the impression I get from this particular song, but I guess from a grading perspective, it’s like a 65 in lyrical quality, a 45 on the lyrical content, and probably a solid 60 in song catchiness. Maybe there’s something in the je-ne-sais-quoi category that I’m missing, but there it is.

Contenders for the last spot in the top 10: All Too Well, Innocent, Wonderland

So here we’re down to the most honorable of honorable mentions. These three songs are significant because they were the ones that I had the most reservations about cutting. They could all probably stake a fairly reasonable claim to be ranked above the song I have at #10. But you know, it was either that or give in like a sucker and make it a top 13 list. The best thing about All Too Well is that Taylor Swift’s lyrical chops are on full display here as she weaves a story about looking back in the aftermath of a great love that didn’t last. It’s at least a 70 in lyrical quality, and probably a solid 60 in lyrical content to boot. It’s super sad, though—probably the most realistically sad song in her discography, and I’ve become increasingly conscious of painting things with the “beauty in sadness” brushstroke that can sometimes glorify suffering as if pain is worth the art it produces.

Innocent gained some internet notoriety when it was released for supposedly being a song TS wrote (in response) to Kanye West. I mean, the text supports that interpretation so there’s that. Even removed from that context though, I think this is a song that better expresses the kind of sentiment that Never Grow Up probably should have been about, i.e. growing up is hard, and we would all like to have the kind of support and chances we had as a kid, but in the absence of that, it can be enough for someone to believe in us. It also has way more show-stopping qualities to boot. 55 for song catchiness, 65 for show-stopping abilities, 65 for lyrical content and 55 for lyrical quality? I’m ballparking. 65 for the je-ne-sais-quoi category if you buy into the whole song being a response to Kanye and TS saying, “I think a lot of people expected me to write a song about [West]. But, for me, it was important to write a song to him.”

Wonderland is a song that probably scores a 70/75 on the je-ne-sais-quoi scale as the very last song on the album, 1989, and is exactly what you hope a “last track of an album” song sounds like. In the days of digital music, we lose a little bit of our sense of track arrangement, but I still like the idea of an album being written as a start-to-finish journey. Wonderland scores high for show-stopping capabilities and catchiness. It’s high energy, frenzied, and in its allusions to Alice in Wonderland, presents us with a simple message: believe in the magic, even if it drives you crazy in the end. But I will admit, this is a song that pushed for a spot in the top 10 because of its je-ne-sais-quoi-ness. There’s just something about this song.

  1. Our Song
Song Catchiness:


Show-stopping Capabilities:


Lyrical Content:


Lyrical Quality:




I would say that the strongest point in Our Song’s favor is that it’s the most commercially successful song released that was firmly within the country genre. As much as Taylor Swift has distanced herself from her country roots, I think part of her legacy will always be that she started off in that genre before becoming a pop superstar. It’s the reason she was such a polarizing figure back in the late 2000s, with Our Song being the most often cited example of “good” Taylor Swift by country music lovers. It’s what ultimately pushed this song into the 10th spot on this list.

Not that Our Song doesn’t stand out on its own merits. I mean, it’s catchy as hell, and I can see it being a pretty good opener for a concert. And the sentiment is rather adorable; Taylor Swift would have been pretty young when she wrote/recorded the lyrics—early teens by my estimate—and the idea of young couples having “their song” is a timeless sentiment that I don’t think has gotten any less popular. Even at this point, you can see the beginnings of Taylor Swift’s lyrical chops with lines like, “He’s got a one-hand feel on the steering wheel, the other on my heart.”

  1. Red
Song Catchiness:


Show-stopping Capabilities:


Lyrical Content:


Lyrical Quality:




Red is an example of a song whose title is also used as the title for the album. Whenever artists do this, I always sort of expect the song to be good, which unfortunately doesn’t always turn out to be the case. Fortunately, Red justifies its selection as an album title song, and I can see how it’s a better choice than some of the other titles that would be rather heavy-handed in their implications; it doesn’t demand that Taylor Swift “explain herself,” that way she would have had to if she had named the album State of Grace or Begin Again.

The first verse of Red sets up the rest of the song incredibly well, with its attention to meter, rhyme, and, frankly, its use of similes. Mention “simile” to the general public, and most people come up with grade school stuff like, “She was white as snow,” or “It was fast like a race car.” And considering how… unsophisticated pop artists can sometimes be with their use of poetic devices (looking at you, Katy Perry and your “She’s as sweet as pie, but if you break her heart, she’ll turn cold as a freezer.”), Taylor Swift practically comes off as a poet laureate: “Loving him is like driving a new Maserati down a dead end street; faster than the wind, passionate as sin, ended so suddenly.”

I also sometimes criticize Taylor Swift for pandering to the “she only writes songs about heartbreak” crowd by insisting on releasing heartbreak songs as singles (see: We Are Never Ever Getting Back Together, I Knew You Were Trouble, Blank Space etc.), but this is actually one song about heartbreak that I think she did particularly well, not only because it eschews the “angry ex-girlfriend” sentiment, but also because I think it does a better job at writing about how hard it is to get someone out of your head post-breakup.

But like many of the other songs on this list, it’s also worth noting that it’s also just catchy as hell and great to belt out in the car.

  1. Long Live
Song Catchiness:


Show-stopping Capabilities:


Lyrical Content:


Lyrical Quality:




The closing track to the Speak Now album, Long Live has a similar kind of appeal to it as Wonderland, in the sense that it *feels* like a closing track. There’s a sort of reckless abandon in the music that drives up its show-stopping capabilities, and you can imagine someone (Taylor Swift, perhaps) belting out the lyrics, “Long live the walls we crashed through / All the kingdom lights shine down on me and you,” at the end of a concert.

Long Live is about recognizing the seminal moments in our lives for their significance at the times they occur, regardless of how our feelings about those sorts of moments change with time and perspective. It’s one of the reasons why the triumphs of our past shouldn’t be things about which we feel embarrassed. I’ve noticed that there are times when people’s reactions to the victories of their childhood and young adulthood seem almost indistinguishable from the way they react to recalling their mistakes and follies. It’s curious that we consider that awkward first kiss in junior high as cringeworthy as breaking up with that same person over text a mere few weeks (or months) later—it’s as if we’re relieved to have gained as much distance from our best and worst selves because those versions of our selves were incomplete. But given that, at the time, our best and worst selves were equally incomplete, should we not be far prouder of the things we managed to do as that half-baked-best-version? I happen to think so. And I think Taylor Swift does too: “And the cynics were outraged, screaming ‘This is absurd!’ / Cause for a moment a band of thieves in ripped up jeans got to rule the world.”

The best thing about this song, though, is that it’s not like Taylor Swift doesn’t recognize that time changes all things. In her final stanza, she sings about how we can carry those victories with us, even as the results from those victories aren’t as “forever and always” as we had hoped they’d be when they happened:

Can you take a moment
Promise me this
That you’ll stand by me forever
But if god forbid, fate should step in
And force us into a goodbye
If you have children someday
When they point to the picture
Please tell them my name
Tell them how the crowds went wild
Tell them how I hope they shine

Consider that this is probably the only song on the top 10 that isn’t strictly about love (I mean, it can be, but it doesn’t have to be). So about this whole sentiment that all Taylor Swift does is write angry breakup songs…

Part 2 will follow tomorrow.

One thought on “Guest Post: A Ranking of Taylor Swift’s Best Songs, Part 1

  1. Pingback: Guest Post: A Ranking of Taylor Swift’s Best Songs, Part 2 | Accidental Shelf-Browsing

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