The Ten Best Taylor Swift Songs

The definitive rankings for Taylor Swift’s international best-selling, Grammy-award winning anthology once, and for all.

This story has been sitting in the “Drafts” section of my Medium account ever since Reputation was released last year. It’s not easy choosing only ten songs from the immortal blonde’s repertoire of chart-topping hits, and even harder to choose which of those songs to start this story with. Taylor Swift is easily a once-in-a-lifetime, generation-defining kind of talent. The overall excellence of her complete works can be compared side-by-side to the giants of any age, the Beethoven’s, the Michael Jackson’s, the Rolling Stones’s.

I was first introduced to her music in college but it wasn’t until 2013 that Taylor truly found me. I was a lonely boy walking up and down Capitol Hill in Seattle when the sounds of Taylor’s friendly G chords found me to keep my time. Since then, I’ve followed her meteoric rise to the Queen of Pop and over the years found myself in all different kinds of ruts to her music. Some days were “Sparks Fly”, followed by “Superman”, and other days were “This Love” and “I Know Places”. I’ve somehow listened to her every song without ever even knowing or talking to her. She must be a fun girl to be around.

The following ten songs represent what I think is the best of the very best from Taylor’s aforementioned exceptional catalogue. Through this list, I hope to both introduce her less obsessive fans to some of her unquestionably best songs, and at the same time, for her more hardcore fans, offer up my own opinions on what I think are her best songs. Furthermore, I wish to share with the world how I see Taylor; she’s a tabloid baby and a star-crossed pop icon, that’s of course a given. But shes also the archetypal Upstate girl wrapped in North Face, princess with a heart of gold, party girl, housewife in a green checkered apron, laughing tomboy riding shotgun, loving daughter, and misunderstood, but undeniably classic, artist.

I walked through the door with you, the air was cold

10. All Too Well

Taylor Swift is very beautiful, but her looks were niche to say the best when she first started. She has a serviceable, but not particularly good, voice. Her guitar playing can be considered novice-level. So what makes her the multi-platinum level artist we now know her as? The answer lies in her songwriting. Taylor’s ability to translate her abstract feelings and thoughts onto paper and then accompany it with compelling music is unparalleled, and on full display in “All Too Well”. At 5:28 in length, “All Too Well” is the longest song on “Red”, and it flows like poetry from start to finish. In this song, Taylor fits the simplest of words together like pieces of a puzzle and paints a grand picture of a perfectly normal relationship, something that seems to woefully escape her in reality. It’s the first song to make the cut.

’Cause we were both young when I first saw you

9. Love Story

It’s easy to forget that Taylor is just like any other girl. She too had to work hard, persevere, and have a little luck to earn her shining star in the sky. And it’s a universal truth that all little girls keep to themselves a dream of courtly love and being a princess. So whether if you’re listening to it in the shower, or simply singing it together with the good ol’ boys, “Love Story” proves that dreams don’t ever have to grow up. I don’t think either Taylor Lautner or John Mayer was quite what she was picturing for “Romeo”, but you can’t fault her for having at least having tried. “Love Story”, the breakthrough hit song that firmly established her in the mainstream and won her the hearts of millions across America, comes in our number 9 slot.

Now I’m in a cab, I tell him where your place is

8. I Don’t Wanna Live Forever (Fifty Shades Darker)

For some reason, it’s hard to imagine Taylor Swift having sex. Maybe it’s her height, or maybe it’s her complete lack of fully developed woman parts. But more likely it’s a job well done by her publicity team. It was incredibly difficult to find a respectable photo of Taylor where she is highly sexualized, so I settled on the one above. She firmly establishes herself as a sex symbol with “I Don’t Wanna Live Forever” for the S&M movie “Fifty Shades Darker”, as in now she looks like she’s actually done it before. As a work of art, there are plenty of other songs that could have taken this one’s place, but as a symbol of change in her career, and as it’s her most played song on Spotify, her collaboration “I Don’t Wanna Live Forever” slides in on our list at #8.

I dared you to kiss me, and ran when you tried

7. “Mary’s Song (Oh My My My)”

I don’t think Taylor ever planned to be simply a country star. She was just 16 when she released that first album and her talent has grown by leaps and bounds since. However, this list would have been desperately incomplete without drawing at least one song from where the flower of T-Swift bloomed, her country roots. It was difficult to pick between “Our Song” (the closest contender), “Should’ve Said No”, and “Tim McGraw”, all of which could have easily taken this slot, but eventually I decided on “Mary’s Song (Oh My My My)”. It evokes an enduring image of love in the South, of two kids growing up dancing around a peach tree, chasing sunsets and fireflies, meant to be. It’s incredibly catchy and among my favorites on the album because its so fresh. It has many of the same sounds as her other more famous songs from her self-titled debut album “Taylor Swift”, but it somehow means more, perhaps because I know less people appreciate it. “Mary’s Song (Oh My My My)” is our lucky number seven.

Long live all the mountains we moved,
I had the time of my life fighting dragons with you

6. Long Live

Taylor’s understandably took a step back for “Speak Now”, the follow-up album to her previous Album of the Year. But she left nothing on the table for this closing track. Flights of high fantasy reign atop the marching chords of this ballad. In “Long Live”, she demonstrates that she knows just why writing is so fun; holding the pen means knowing you can write the story however you imagine. And Taylor has her full share of make-believe fun in what I believe is the best song on her “Speak Now” album. “Long Live” is #6 on this list of Taylor Swift’s best songs.

We’ve reached the halfway point now on our drive down Taylor Swift Lane. The previous five songs can be shuffled back and forth depending on the day, the weather, your mood, perhaps even substituted. But for the songs that reside above, they are taken from Mt. Sinai. There can be no mistake that the following five songs stand tall as the giants among Taylor’s works. They are feats of musicianship, golden opportunities of zeitgeist, and personal stories told for the world to see, all in one. Forth!

You don’t know about me,
But I’ll bet you want to

5. 22

It’s hard to find a good and proper song where ol’ Tay Tay is happy. Seems like she finally found bliss in “22”, her no-holds-barred anthem to having fun and being the life of a party. To those of us observing from the sidelines, we’ll forever stare in amazement at the kind of lively energy she was able to effortlessly bottle into this song. To Taylor, oblivious, she will never fully realize just how much joy she brings to everyone watching when she’s on. And that’s the only way to do it. “22” is the first step up to Taylor Swift nirvana.

My baby’s fly like a jet stream,
High above the whole scene,
Loves me like I’m brand new

4. Call It What You Want

Taylor’s latest album “Reputation” is ambitious but overall a miss musically. Hearing “Call It What You Want” however is proof that her already deep well of songwriting goes even deeper still. She explores more complex rhythm structures and plays with different accents than her listeners are used to, but always ends up tying it together with her trademark potent simplicity. Taylor Swift rap god. “Call It What You Want” brings us yet another step closer to the end, rounding up the top 4 Taylor Swift songs. Can you feel the wind picking up?

And you know I wanna ask you to dance right there,
In the middle of the parking lot,
Yeah

3. Fearless

The world was a place full of fear before 2008. And then there was “Fearless”. World, please meet Taylor Alison Swift. The title track off that momentous album is a classic in every sense of the word. It’s not too long, not too short, not too noisy, and not too quiet. Listen with half an ear and it sounds meaningless, listen closely and feel chills. It appeals to the teenage girl just as much as it appeals to her mother. It’s just the right beginning to what is still Taylor’s most complete album. It’s “Fearless”, and it’s our bronze.

You got that long hair, slicked back, white t-shirt
And I got that good girl faith, and a tight little skirt

2. Style

This song was surely inspired by Taylor’s ease of navigating down the cobblestones South of Houston in heels. A twisting riff at the start drives the listener forward immediately, and the head-banging chorus in answer is a promise kept. “Style” somehow manages to both evoke images of Americana and cyberpunk simultaneously. This is at once a night drive song, a walk to work song, a break-up in the bedroom song. It’s a song about a relationship. It’s a song about love. It’s the centuries-old play between a female on full display and a male with every one of his cards laid out on the table. The speed at which “Style” moves without a hitch showcases her mastery of pop, and the lyrics themselves contain a wealth of deep archetypal work, symbolism and damn good songwriting. “Style”, the lone representative on this list from Taylor’s second Album Of The Year “1989”, cements the enduring image of a modern Taylor Swift, and is our runner-up.

And I love you for giving me your eyes,
For staying back and watching me shine, and

1. The Best Day

Being a Taylor Swift fan as a guy is strange. It’s always a bit embarrassing whenever I’m playing her music in front of my friends; they always seem to think that I just have a silly boy crush on her. Sure, I came for the looks, but I stayed for the music. I always wordlessly queue this song after my friends have had their fill of her crowd-pleasing pop hits, and as the first chords of “The Best Day” start, they always grow silent to listen.

Thank you for reading and coming along on this journey of Taylor Swift-o-mania with me. I’d imagine that if one were to play all of Taylor Swift’s 129 songs back to back, never to be played again, “The Best Day” would the last to be played. And that’s why Taylor’s gloriously simple ode to childhood, family and growing up is number one. It evokes the rolling credits and the golden setting sun of a entire woman’s life put to work, still, ten years after its writing. It don’t get any more classic than that.

The story of my relationship with Taylor ends here. When I started writing this, I thought it would simply be a top 10 list, but slowly I realized it had turned into a eulogy. Not tragic, but perhaps bittersweet, as most endings tend to be. To her fans, I am curious as to what you have to say about this list; do you share my perspective? If not, how have you come to appreciate her music? And of course, to Taylor, thank you. Don’t make us wait too long for what comes next!