Despite her young age (twenty-five years old!), Swift has a substantial discography: five albums and countless singles and guest appearances. Needless to say, sorting through her songs is a slightly grueling task. This was particularly true for me, a dedicated Swiftie since 2006. I have followed her evolution from spunky country teen to sophisticated chanteuse, and my emotional investment in her music is high. Goodness knows it took a million years longer than I wanted it to, but I actually managed to finish this list, in spite of my compulsion to change it daily.
So on to the good stuff...
You'll notice a "Best Moment" for each song. Taylor Swift is all about moments -- from the casually beautiful to the monumentally tragic -- and it shows in her craftsmanship. Whether with a clever couplet or expressive delivery, she knows how to take listeners by surprise and turn a good song into a great one or a great one into a classic in a matter of seconds.
One last thing before I get started! I left out the following:
- Songs where Taylor is a featured artist (e.g. Half of My Heart)
- Live covers (e.g. Drops of Jupiter)
- Holiday songs (e.g. Last Christmas)
- Acoustic or remixed versions of her songs
- Songs not available on iTunes
Love her or hate her (for shame!), check out the list and tell me your own Swiftian faves!
The Kinda Sorta Definitive Ranking of Taylor Swift's Songs
83-71
This is a pleasant enough song, but it's too generic to rank with the best of Taylor's wistful breakup pleas. She'll cover this territory better on later songs.
Best Moment: When she lets her then-thin voice glide skyward at the end of "How do I get it back the way it was before?" It's a nice mix of melancholy and sweetness.
82. "Superstar" - Fearless (Platinum Edition)
I like the idea of this song, and I like a lot of the lyrics, but the musical structure is dull. Snore.
Best Moment: Probably the descriptive first verse, which paints the anomalous picture of Taylor as just a face in the crowd, summing up the song's conceit.
81. "Sweeter Than Fiction" - One Chance Motion Picture Soundtrack
This cinematic theme song feels like a precursor to 1989, all candy-coated synths and drum machines. That's no surprise, as it is a collaboration with fun.'s Jack Antonoff. I just wish the lyrics were more interesting. Vaguely triumphant Taylor is never my favorite Taylor. It's her least flattering look, always missing her signature slice-of-life details.
Best Moment: The '80s instrumental intro, which sounds like it should play at the start of a John Hughes movie.
80. "Change" - Fearless
Vaguely Triumphant Taylor returns, this time for the 2008 Olympics! At least the production is better here than on the frustratingly muddled "Sweeter Than Fiction." And the anthemic chorus is an earworm.
Best Moment: I suppose when she wails "Hallelujah!" It's the kind of stock phrase that you can inject a lot of feeling into, and Taylor gives it her best shot.
This cinematic theme song feels like a precursor to 1989, all candy-coated synths and drum machines. That's no surprise, as it is a collaboration with fun.'s Jack Antonoff. I just wish the lyrics were more interesting. Vaguely triumphant Taylor is never my favorite Taylor. It's her least flattering look, always missing her signature slice-of-life details.
Best Moment: The '80s instrumental intro, which sounds like it should play at the start of a John Hughes movie.
80. "Change" - Fearless
Vaguely Triumphant Taylor returns, this time for the 2008 Olympics! At least the production is better here than on the frustratingly muddled "Sweeter Than Fiction." And the anthemic chorus is an earworm.
Best Moment: I suppose when she wails "Hallelujah!" It's the kind of stock phrase that you can inject a lot of feeling into, and Taylor gives it her best shot.
79. "The Other Side of the Door" - Fearless (Platinum Edition)
This is a catchy song with some compelling imagery, but it also kind of sounds like a country-fied Hilary Duff song. I love me some Hilary Duff, but she hasn't exactly established herself as a formidable artist the way Taylor Swift has. In other words: I want and expect more from Taylor Swift.
Best Moment: The singalong chorus? The mysterious last verse? Those stand out, but I'm going with
This is a catchy song with some compelling imagery, but it also kind of sounds like a country-fied Hilary Duff song. I love me some Hilary Duff, but she hasn't exactly established herself as a formidable artist the way Taylor Swift has. In other words: I want and expect more from Taylor Swift.
Best Moment: The singalong chorus? The mysterious last verse? Those stand out, but I'm going with
Me and my stupid pride are sitting here aloneIt's a rare early acknowledgement of her faults, basically a unicorn on her first two albums.
Going through the photographs, staring at the phone
I keep going back over things we both said
And I remember the slamming door and all the things that I misread
This song would rank higher if it didn't repeat itself ad nauseam. But the beginning is arresting, like Swift is performing with a small band in the middle of the desert at midnight.
Best Moment: The stripped down instrumentals are dreamy, so any part where those are featured (e.g. the first verse or last lines).
Classic Taylor, in which she admires a boy who likes someone else from afar. It's dramatic and immature and features a serious case of tunnel vision, but it's also very real because teens are often dramatic and immature and only see what they want to see. Capturing youth has always been one of Taylor Swift's strong points, and that's on display here, in all of its embarrassing glory. But it's also kind of a musical bore and lacks the lyrical fervor of other songs with the same subject matter.
Best Moment: "We could be a beautiful miracle, unbelievable, instead of just invisible." I love this because it's so over the top but sounds like she really means it. I hope this is a line Taylor looks back on now and laughs at, but not without a hint a nostalgia.
76. "The Outside" - Taylor Swift
If this sounds like it's about an angsty adolescent feeling like she doesn't fit in, that's because it is. Taylor Swift wrote this song when she was twelve years old. Surely it was tweaked before her debut was released four years later, but it is still impressive that someone so young could produce such a polished piece of country-pop. There's nothing groundbreaking here, but it's a bit like iced tea -- sweet and slides down easy. A catchy little tune.
Best Moment: "I've been a lot of lonely places/I've never been on the outside." Aw, poor baby Swift. She's not angry, just disappointed and confused.
I've always liked this girl power anthem, even if it's a little melodramatic. I'm sure many young people can relate to the notion of just "trying to find a place in this world." And the big chorus demands you sing along.
74. "Never Grow Up" - Speak Now
A melancholy cousin to "The Best Day." Taylor sleepily walks listeners through childhood and adolescence, imploring them to "never grow up." The lyrics feature colorful snapshots of youth, like being dropped off at the movies and dancing your pajamas. But it is perhaps a little too drowsy, more likely to induce nap time than catharsis.
Best Moment: When Taylor whimpers a regretful "I wish I'd never grown up." It most clearly illustrates how personal this is for her.
A lot of fans love this one, and it is indeed a touching tribute to her mother, but the arrangement is just too cutesy. I love adorable Taylor, cute Taylor, but occasionally she crosses a fine line and verges on cloying. The combination of the sentimental lyrics (which I like), the simple instrumentals (which I don't like), and Taylor's childlike delivery (meh) makes "The Best Day" one of her twee songs.
But the music video is lovely, and you should watch it.
Best Moment: "I know you were on my side/Even when I was wrong" With more grown-up eyes, Taylor realizes just how much her mother has done for her and stood by her. She's more than just the lady who took her to pumpkin patches and let her paint in the kitchen; she's a faithful guardian who would never leave. Swift's emotional utterance of these lines drives the point home.
72. "Come in With the Rain" - Fearless (Platinum Edition)
I am a sucker for potent imagery. This song has it. You can easily picture a hopeful but weary Swift sitting alone in her room, plaintively watching a storm rage. Suddenly inspired, she pulls out a notebook and writes this song.
Beyond that, I like the overall lyrical structure. She starts by telling her love interest all the things she could do to make things better. Then she pushes the responsibility into his hands because she's tired of doing all the work. Finally, she lays everything on the table with the chorus. It's sophisticated songwriting, textbook Taylor.
Best Moment: "I’ll leave my window open/‘Cause I’m too tired at night to call your name." Perfectly captures her exhaustion with trying to keep a fading relationship alive.
71. "Innocent" - Speak Now
This song is supposedly about Kanye West and consequently feels really hokey. It doesn't help that Kanye's take on the VMA controversy is so much better. But "Innocent" has some absolutely beautiful moments. I'm torn. How about we keep the mystical verses and get rid of the clumsy chorus? Except for the "string of lights" line. Pretty gorgeous.
Best Moment: The aforementioned line. It's a fresh take on one of music's favorite motifs, and it flows in a way the rest of the chorus doesn't.
72. "Come in With the Rain" - Fearless (Platinum Edition)
I am a sucker for potent imagery. This song has it. You can easily picture a hopeful but weary Swift sitting alone in her room, plaintively watching a storm rage. Suddenly inspired, she pulls out a notebook and writes this song.
Beyond that, I like the overall lyrical structure. She starts by telling her love interest all the things she could do to make things better. Then she pushes the responsibility into his hands because she's tired of doing all the work. Finally, she lays everything on the table with the chorus. It's sophisticated songwriting, textbook Taylor.
Best Moment: "I’ll leave my window open/‘Cause I’m too tired at night to call your name." Perfectly captures her exhaustion with trying to keep a fading relationship alive.
71. "Innocent" - Speak Now
This song is supposedly about Kanye West and consequently feels really hokey. It doesn't help that Kanye's take on the VMA controversy is so much better. But "Innocent" has some absolutely beautiful moments. I'm torn. How about we keep the mystical verses and get rid of the clumsy chorus? Except for the "string of lights" line. Pretty gorgeous.Best Moment: The aforementioned line. It's a fresh take on one of music's favorite motifs, and it flows in a way the rest of the chorus doesn't.
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