Note: This article was written on December 2, before the announcement and release of Swift’s most recent album Evermore, so it does not mention any songs from the album.

As we near the end of 2020, the annual trend of people posting their “Spotify: Wrapped” lists on social media continues. If you don’t know what “Spotify: Wrapped” is, it’s essentially a personal look-back or review of all the music a Spotify user listened to for the past year, including a ‘top 5’ list of the user’s most-played artists and songs. And once again, I saw Taylor Swift dominate many top-played artists lists just as she appears to dominate the Billboard charts year after year. 

Most of the songs by Swift that I saw on top-played songs lists were from her most recent album, folklore (released in July 2020, so understandably so), but as a fan who prefers her older stuff, I find myself listening to more of her throwback hits on a regular basis than her newer released music (don’t get me wrong though, I still really enjoyed folklore). With the increased amount of Swift that I was seeing on my timeline in addition to the recent news of Swift finally beginning to re-record all of her old tracks, I decided it’d be a fun idea to go back through the years and try to choose five of my favorite all-time tracks by Swift.

That being said, I’m terrible when it comes to ranking favorite songs and I especially struggled with trying to narrow down my favorites to a mere five tracks. Additionally, my list of favorite songs by any artist—or in general—is prone to change every couple of months depending on my mood or how much I overplay a song. But without further ado, here’s my personal list of my top five favorite Taylor Swift songs, in no particular order (with honorable mentions at the end!):

THE LIST

Love Story (from Fearless)

This might honestly be my number one favorite Taylor Swift song of them all. I normally get tired of songs for periods of time after I overplay them for a while, but Love Story, for how iconic it is as one of Swift’s most popular tracks of her career, has consistently been one of my most favorite songs that I have not worn out. Most of my most-played songs belong to the rap or R&B genre, so this song does admittedly feel out of place among them, but that’s just how much of a banger it truly is. 

It tells the age-old romance tale of Romeo and Juliet but with the twist of a happy ending rather than the tragic ending we’re all familiar with. The instrumental—consisting of banjo, acoustic and bass guitar, drums, violin, and more—paired with the country twang of Swift’s voice is just perfection; the build-up from a light country-pop track during the beginning to a more percussion-heavy chorus and climax at the end really adds to the overall feeling of the song. And that isn’t to mention how amazingly catchy the lyrics are without sounding repetitive. I’m sorry, but if this timeless song doesn’t have you singing along to “It’s a love story, baby, just say yes,” then no song ever will.

You Are In Love (from 1989)

Alright, this one isn’t nearly as catchy or popular as some of her other tracks but it’s still a bop regardless. It’s a bonus track for her album 1989, and if you had never heard of Taylor Swift before 1989 then you would’ve never guessed that she was once a country-pop singer. Swift’s slight country accent is noticeably gone for this record but her songwriting and singing talents are still very much present.

You Are In Love is a tranquil and soothing track that really captures the essence of a late-night drive. And it’s not just the lyrics, “small talk, he drives, coffee at midnight,” that give it that feel either—it’s the song’s entire sound. From the harmony and echoed lyrics in the chorus to the soft, whisper-ish tone of her voice in the verses in between, Swift puts together a beautifully crafted track that I personally think goes underappreciated in comparison to the rest of her discography. 

Enchanted (from Speak Now)

This track is particularly special to me because it’s the song that got me back into Taylor Swift after an extended break of not listening to her. You know those songs in your library that are just there and that you typically skip when they come up on shuffle? Enchanted was one of them until it came up on shuffle for me one day and I decided to listen all the way through just for the hell of it. I was pleasantly surprised; it had been a while since I heard it and it sounded a lot better than what I remembered.

I used to be embarrassed by some of the kinds of music that I listened to, especially when it came to artists like Taylor Swift because it wasn’t the type of music other guys my age were listening to. Eventually, I learned to just not care about what other people thought and came to embrace all different types of music, and Enchanted was one of those first steps in the right direction for me.

It’s an excellent showcase of Swift’s songwriting and storytelling abilities as well as her versatility as an artist. The song blends pop-rock, ballad, and country elements together to tell the story of her interaction with Owl City’s Adam Young and how she was “enchanted” to meet him. The build-up from the light, acoustic verses to the heavier, pop rock-inspired chorus dominated by percussion to the eventual electric guitar solo and then the ending “please don’t be in love with someone else, please don’t have somebody waiting on you,” is just perfection.

Hey Stephen (from Fearless)

There’s something about this song I can’t exactly put a finger on that just really appeals to me. It’s not a gut-wrenching emotional ballad or a particularly stand-out piece of songwriting relative to the rest of Swift’s discography or anything of that sort; it’s just a simple, catchy, and cheery song about a crush. And yet, there’s something about it that makes it sound really special.

I think this song is a perfect representation of Taylor Swift’s older music, when she was younger and writing simple catchy country-pop love songs with her acoustic guitar being the other star of the show (think: Teardrops On My Guitar, Our Song, Fifteen, etc.) Hey Stephen is just that; it’s not lyrically complex and doesn’t intimately explore themes, such as heartbreak or retrospection or anything like that, but it’s a charming, innocent love song that feels authentic and just sounds good.

Crazier (from Hannah Montana: The Movie Soundtrack)

I admit this one might be a little (or very) controversial—which is why I saved it for last—but just hear me out. You won’t find this song on any of Swift’s albums or even singles and that’s because it was written for a movie soundtrack—the Hannah Montana: The Movie soundtrack, to be exact. Now, I might be misjudging the popularity of this song but to me, Crazier is crazily underrated (pun intended, unfortunately).

It’s a slower, softer country-pop ballad that really showcases Swift’s soulful vocals and allows her country drawl to shine through. This song to me is the dictionary definition of nostalgia comfort; for all the flaws that Hannah Montana: The Movie had, the scene where this song played was definitely the highlight of the movie. What’s crazy is that she originally wrote the song when she was just 13, but it feels genuine and full of youthful innocence and emotion.

It might not be one of her more iconic tracks or even one that especially showcases her talents, but it’s a personal favorite that holds a special place in my childhood and currently shares the top spot on my nostalgic pop playlist alongside the Jonas Brothers’ Lovebug. If I’m being real though, it can easily (and probably should) be replaced by any of the honorable mentions.

Honorable Mentions:

You Belong With Me (from Fearless)

Come on now, you didn’t think I’d leave this song completely off the list without at least an honorable mention, did you? After Love Story, this is probably the most quintessential Taylor Swift song. If you’re old enough to remember the pop era around 2009, chances are you probably know the lyrics to most if not all of this song by heart. Now trust me, I’m no singer by any means, but if this song doesn’t have you belting, “she wears short skirts, I wear t-shirts; she’s cheer captain and I’m on the bleachers,” in the shower or in the car, then there must be something wrong with you.

And if those lyrics don’t ring a bell, you’re just missing out on the masterpiece that is this song—and the entire Fearless album for that matter. At the very least, you should recognize the iconic music video that features Taylor Swift exchanging messages through the window with her next-door neighbor/crush. Fun fact: the actor (Lucas Till) who plays Miley Cyrus’s love interest in Hannah Montana: The Movie, in which the track Crazier is featured, is actually the same actor who plays Taylor Swift’s love interest in her iconic You Belong With Me music video.

Mirrorball (from folklore)

If I’m being honest, this song could’ve probably made the top five along with a couple of other songs on the honorable mentions list; the difference in my preference for the songs in my top five versus my honorable mentions is marginal and can honestly switch day-to-day. The biggest thing that caused me to hesitate with putting it in my top five is that it’s still a relatively new song and so it hasn’t stood the test of time yet for me. 

I mentioned that I can get tired of some songs pretty easily especially if I overplay them, but I’ve known and loved each of the songs in the top five for a while now and I can’t say the same for this track quite yet. It’s definitely my favorite song off of folklore though and it might just end up cracking my top five later on. I mean, it truly is a beautiful and catchy song that gives off a serene, winter vibe.

All Too Well (from Red)

It’s five-and-a-half minutes of heartbreaking, raw emotion in the form of a ballad. (Are you starting to see a pattern on this list?) One of Taylor Swift’s infamous track fives on her (arguably) most masterfully written album, it’s widely regarded as one of her greatest songs—what more has to be said?

I actually struggled choosing between this song and Enchanted for the top five because they’re pretty similar to me—not sound-wise but in regards to the fact that they’re both eloquent, emotional ballads (despite one being about heartbreak and the other being about meeting somebody for the first time)—but I ultimately ended up choosing Enchanted because it just sounded better to me personally. 

However, the verse into which the guitar solo leads with the lyrics: “and maybe we got lost in translation, maybe I asked for too much, but maybe this thing was a masterpiece ‘til you tore it all apart,” is honestly one of my favorite parts/verses of any Taylor Swift song ever. All Too Well really is beautifully written and looking back, it definitely deserves to be put in the top-five list over Crazier, but I couldn’t help but let the nostalgia of Crazier get the best of me.

The Last Time (feat. Gary Lightbody) (from Red)

I personally consider this Swift’s best duet/collab song, even better than folklore’s exile featuring Bon Iver. Lightbody’s (better known as the lead singer for alt-rock band Snow Patrol) and Swift’s voices blend together beautifully on this track about forgiveness, apologies, and an ultimately failing relationship. Like many of Swift’s emotional ballads, it starts off soft and has a gradual build-up to an intense climax. 

At the end of the song, the two repeat each others’ lines: “This is the last time I’m asking you this (this is the last time I’m asking you this), put my name at the top of your list (put my name at the top of your list), this is the last time I’m asking you why (this is the last time I’m asking you why)…” which is one of the parts of the song that really stand out to me because of how cleverly written it was—despite Swift and Lightbody singing the exact same lyrics, the meanings behind them are respectively different. And oh man, don’t let me get started on the brief back and forth that the two share in the bridge of the song. Do yourself a favor and listen to this gem of a song if you haven’t already, you won’t regret it.

Fifteen (from Fearless)

I’m not going to go too in-depth about this song because I like it for more or less the same reasons as Hey Stephen (but obviously less so because otherwise, it would be in the top-five), but I know what you’re thinking right now. Another song from Fearless? Yes, another one; after all, it is the album that earned Swift her first Grammy award as well as her best album and—and that’s a hill I’m willing to die on.