In which Mattie conveniently lists out the best 15 songs Miss Swift has ever released since her debut album.
Being on the cusp of a new Taylor Swift era, I thought it would be fun to take a look at Taylor’s past work and perhaps help other people decide which songs they should start with when beginning to listen to Taylor Swift’s music. Although my list is completely subjective, keep in mind that I have now been a Swift super-fan for 10+ years and I probably know what I’m talking about. Without further ado…
15. Hey Stephan
Beginning with a sweet hum, Hey Stephan is an adorable ode to a crush who doesn’t know he’s being crushed on — otherwise known as a classic Taylor Swift theme. Although it masquerades as a simple song, lyrically this song inspired tween girls all over the world in 2008 to begin their attempts at writing songs and to perfect their humming.
Favorite lyric: “Hey Stephan, I could give you fifty reasons why I should be the one you choose/ All those other girls, well they’re beautiful, but would they write a song for you?”
After the infamous incident at the 2008 VMAs where Kanye West took the mic from then-19 years old Taylor Swift, who could’ve predicted the wreckage that would come from it? Innocent was young Swift’s way of telling Kayne (and anyone else who listened to this song) that she forgave him for embarrassing her in front of the entire world. Mature and moving, Innocent is worded just vaguely enough so any teenager can apply the lyrics to their own life.
Favorite lyric: “Time turns flames to embers/You’ll have new Septembers/Every one of us has messed up too/Minds change like the weather/I hope you remember/Today is never too late to be brand new”
13. Love Story
The quintessential Taylor Swift song that everyone enjoys when it’s play — this song was inescapable back in 2008 when it was released. Becoming one of Swift’s most successful songs to date, this song was the perfect pop-country crossover that became Swift’s brand at the start of her career. This song is also important to note as it is the first song in her discography that uses the “mention something at the beginning of the song and then refer to said thing at the very end to tie the whole song together” scheme that Swift has employed in countless songs since.
Favorite lyric: “You’ll be the prince and I’ll be the princess/It’s a love story, baby just say ‘Yes'”
12. The Best Day
A personal favorite of mine, The Best Day is the song Swift wrote for her mother, Andrea Swift. Not only is this song incredibly touching and intimate, it showed how much Swift’s songwriting grew in between 2006 and 2008 (when the song was released). The way the verses are set up and how they seamlessly flow into the chorus is something that professional songwriters envy from afar; The Best Day showcases how Swift is truly a writer at heart.
Favorite lyric: “I have an excellent father, his strength is making me stronger/God smiles on my little brother, inside and out, he’s better than I am/ I grew up in a pretty house and I had space to run/And I had the best days with you”
11. Our Song
Another classic Taylor Swift song, Our Song was one of Swift’s first singles off of her debut album. This song struck me back in the day when I heard Swift’s twangy voice sing “He’s got a one-hand feel on the steering wheel and the other on my heart.” I remember looking it up on Google and finding that she was only 15 when she wrote those lines — 15! If I could write a lyric half as well at 21 as she wrote that one when she was 15, I would consider myself set for life.
Favorite lyric: “I was riding shotgun with my hair undone in the front seat of his car/I grabbed a pen and an old napkin/And I wrote down our song”
10. Sad Beautiful Tragic
A dismal, but remarkably beautiful song, Sad Beautiful Tragic haunts its listeners long after the song is over. One of Swift’s best songs lyrically to date, it reminisces over a long gone relationship where neither person seemed to win after the breakup. It’s a song to experience rather than to read about.
Favorite lyric: “And time, is taking its sweet time erasing you/And you’ve got your demons, and darling they all look like me”
9. Dear John
Fighting for its deserved spot to be Swift’s best written song, Dear John is a powerful and desperately sad song written with famous ex John Mayer in mind. Swift really honed in all of her songwriting expertise to piece together this masterpiece — depicting strong emotions in every single line, this song is best listened to after a breakup with a glass of wine in hand.
Favorite lyric: “And you’ll add my name to your long list of traitors who don’t understand/And I’ll look back and regret how I ignored when they said/’Run as fast as you can'”
8. Tim McGraw
The song that started it all, Tim McGraw was Swift’s debut single off her very first album released in 2006. This song brings to mind summer nights, starry skies, and a short-lived fling who you secretly wished had stayed with you longer. After reading the lyrics, I was amazed that a 15 year old wrote this song… HOW does she do it? I guess that’s why she became famous — no one else at the time could write songs about teenage summer romance quite like Taylor Swift could.
Favorite lyric: “September saw a month of tears/And thankin’ God you weren’t here to see me like that”
7. State of Grace
A booming entrance to Swift’s fourth album, Red, State of Grace sets the tone for the rest of the album. Set against noisy drums and guitars, Swift does not struggle to be heard against her rowdy background. Another winner in terms of lyrics, Swift does not hold back in her usual way of being extremely intimate with her lyrics.
Favorite lyric: “So you were never a saint/And I’ve loved in shades of wrong/We learned to live with the pain/Mosaic broken hearts/But this love is brave and wild”
6. All Too Well
A favorite among Swift’s fan base, All Too Well is praised as being Swift’s best song of all time. Obviously, opinions can’t be shared by all seeing that it made #6 on my list, but I’m not going to deny that it is a fantastic song. Arguably her most confessional song ever released, Swift bares all in her remembrance of a relationship turned sour.
Favorite lyric: “Hey, you call me up again just to break me like a promise/So casually cruel in the name of being honest/I’m a crumpled up piece of paper lying here/Because I remember it all, all, all too well”
The original favorite of the Swift fandom before All Too Well came along, Enchanted was the song every Swiftie looked forward to at the Speak Now tour. One could call this just another Taylor Swift song about longing after a crush, or you could say what it really is: a striking and startlingly honest tribute to a person Swift made a deep connection with after only meeting once. I think we’ve all had the experience of clicking with someone immediately even if we don’t know and Swift perfectly depicts every moment of how that feels.
Favorite lyric: “This night is sparkling, don’t you let it go/I’m wonderstruck, blushing all the way home/I’ll spend forever wondering if you knew/I was enchanted to meet you”
4. New Romantics
Hiding on the deluxe edition of 1989, New Romantics is perhaps the best kept secret among the Swift fandom. Glittery, exciting, and extremely sarcastic, New Romantics somehow embodies Swift’s personality all under 4 minutes. This song shows Swift has overcome all of the negativity surrounding her career and has made an empire to show off her happiness.
Favorite lyric: “Please take my hand and/Please take me dancing and/Please leave me stranded, it’s so romantic”
3. You Are In Love
Another song lurking on the deluxe edition of 1989, You Are In Love deserved to be on the regular edition of the album. Gorgeous imagery and full of emotion, this song has been taken for grated for too long. You Are In Love is Swift’s song dedicated to her friends whom she observed as their relationship flourished right before her. And being Taylor Swift, how could she not write a song about a love that was happening right before her eyes?
Favorite lyric: “One night he wakes, strange look on his face/Pauses, then says, ‘You’re my best friend’/And you knew what it was/He is in love”
2. Blank Space
I love Blank Space solely because it shows how Swift truly will always have the upper hand over everyone who makes fun of her. Media makes up stories about her being a crazy boy-obsessed ex-girlfriend? Fine, Swift thought, that would make a hilarious and witty background for a song. No matter what is thrown at her, Swift is always able to turn the tables back around and laugh at herself. And having this ability, Swift will always end up on top. A satirical song with a bite, Swift nods her head at all her critics while still keeping her poise.
Favorite line: “Darling I’m a nightmare dressed like a daydream”
The winner of my list!! Style stood out to me immediately when I heard 1989 sitting on Taylor Swift’s living room floor. It opens up with a cool 80’s synth-pop beat that is unheard of today’s music, but Swift’s voice remains cool and unbothered as she explains to her listeners the story of her and a former lover. Cheekily named Style after Harry Styles, the subject of the song, Swift calls both herself and Styles out for the downfall of their relationship. There is more than what what meets the eye with Style, and much of the song’s message lies in between the lyrics.
Favorite lyric: “I should just tell you to leave ’cause I/Know exactly where it leads but I/Watch it go round and round each time”