Revisiting Taylor Swift’s Best Songs: My Top 20

Once this post goes live, we will be less than 48 hours away from Taylor Swift releasing her 7th studio album and you better believe I am FLIPPING OUT!

As I type this blog post, we’re just in the beginning stages of the album release week. With that being said, I wanted to share an updated version of a post I did around this time two years ago a couple months before reputation was released. Obviously this one is much closer to the release date since we’re in the thick of it! I wanted to do a Taylor-related post since this is obviously the main thing I will be thinking about for the next couple weeks in regards to music and new releases. I am not sure if I will listen to anything else that is released this Friday, to be honest.

Like I mentioned above, I did a post on this two years ago with my top 10 Taylor songs and a podcast earlier this year on my five favorite songs across each album. I think that this list is overall similar but since I’ve had some time for reputation to sink in, it’s changed a bit since the first post went live on August 23, 2017. You can check it out here.

This time around I want to include my top 20 songs but won’t be going as in-depth with each one. As I compared my list from today vs. two years ago, it’s crazy to see how different it actually became. A lot of the songs in general are still in the top but the order has definitely changed!

Key
Taylor Swift – blue
Fearless – green
Speak Nowpink
Redred
1989purple
reputation – black

1. “All Too Well”

There are actually Taylor Swift fans out in the world who believe that this song is overrated and boy do I have to laugh. Not only was this Taylor’s personal favorite song she’s ever written (apparently she’s told a fan that her new favorite is on Lover), but “All Too Well” was arguably the track that helped Taylor gain critical acclaim for her songwriting capabilities. This song has continued to change and grow in meaning for me as I grow older and that’s an unparalleled feeling to me.

Favorite Moment: “You call me up again just to break me like a promise. So casually cruel in the name of being honest” and “Time won’t fly, it’s like I’m paralyzed by it, I’d like to be my old self again, but I’m still trying to find it”

2. “Out Of The Woods”

This song and ATW constantly battle for my favorite song because they mean so much to me. I think I’ve shared this before, but this song came out in a time of my life where I really needed to hear it, and for that reason specifically is why it means so much to me. I love the lyrics, the production and the bridge and their ability to tell a story of feeling anxious, uneasy and battling conflicting feelings in a relationship. I think it’s the perfect example of Taylor as a musician and it also helps that Jack Antonoff was involved in its creation.

Favorite Moment: Remember when we couldn’t take the heat / I walked out, I said, I’m setting you free / But the monsters turned out to be just trees / When the sun came up you were looking at me”

3. “State Of Grace” 

I’ve said it once and I’ll say it again – this song is the epitome of my favorite Taylor Swift sound. I love the production, the indie pop vibes, all of it. It’s a beautiful song about having just the perfect amount of bliss with someone in the beginning stages and being able to think about all of the potential without being jaded about it. And I find it interesting and goofy that so much of Taylor’s career has been poked at for her songwriting about heartbreaks when this one is so clearly NOT about a heartbreak.

Favorite Moment: “Love is a ruthless game / Unless you play it good and right / These are the hands of fate / You’re my Achilles heel / This is the golden age of something good and right and real”

4. “Holy Ground”

Similar to what I said about the song above, this song also paints a picture of a newly formed relationship and the excitement of those first moments with someone. There is something so unbelievably beautiful about Taylor’s ability to write songs reminiscing about the past – good and bad. I have a really prominent habit (not sure if it’s good or bad) of associating places with people, and this song reminds me of that tendency a lot.

Favorite Moment: “We blocked the noise with the sound of ‘I need you’ / And for the first time I had something to lose / And I guess we fell apart in the usual way / And the story’s got dust on every page / But sometimes I wonder how you think about it now / And I see your face in every crowd”

5. “Treacherous”

Ladies and gents…here we have it. The most underrated T.Swift song ever. I SAID WHAT I SAID. I am still so absolutely in love with this song and how understated and beautiful it is. From the guitar, production, melody and lyrics, “Treacherous” delves deep into the concept of going for something in spite of it completely terrifying you. I think this song is one of Taylor’s best examples of songwriting and I wish it would stop getting swept under the rug!

Favorite Moment: “I can’t decide if it’s a choice / Getting swept away / I hear the sound of my own voice / Asking you to stay / And all we are is skin and bone / Trained to get along / Forever going with the flow, / But you’re friction”

6. “Fearless”

Nothing quite encapsulates the way a 16-year-old girl feels crushing on a boy in the 2000s like this song does. Romance (for most people that age) is unchartered territory and taking a leap with someone for the FIRST TIME ever (this is at least how I interpret it) is a huge deal that is perfectly and flawlessly described in this song. I think I hold it in my heart so heavily because I just love the message of being scared and choosing to continue in spite of that fear. And that can be applicable to anything!

Favorite Moment: “Well you stood there with me in the doorway / My hands shake / I’m not usually this way but / You pull me in and I’m a little more brave / It’s the first kiss, it’s flawless, really something / it’s fearless”

7. “Clean”

I’ll admit that “Clean” wasn’t initially one of my favorite songs off of 1989 but it grew on me a lot, specifically after I saw Taylor perform in live on tour. My favorite types of songs are ones where the message can be universally understood with different meanings for each person who listens to it and I think “Clean” encapsulates that concept perfectly. It’s coming to terms with being okay with something that has caused you damage – whether that’s a person, a concept, whatever, and that’s a really beautiful and vulnerable message.

Favorite Moment: When the butterflies turned to dust, they covered my whole room / So I punched a hole in the roof / Let the flood carry away all my pictures of you / The water filled my lungs, I screamed so loud but no one heard a thing”

8. “The Story Of Us”

I strongly believe that the feeling of running into someone you were once romantically involved with and not saying a word to them is to me, one of the saddest experiences that any human can go through with another human. This concept rings very true in this track, and it was inspired by Taylor running into John Mayer at an awards show pretty soon after they had broken up (cough cough, their break-up was messy). I can always go back to this song because of how much I relate to it. Chicago’s a big city, but not that big… 

Favorite Moment: “This is looking like a contest / Of who can act like they care less / But I liked it better when you were on my side / The battle’s in your hands now / But I would lay my armor down / If you’d say you’d rather love than fight”

9. “Blank Space”

We love when Taylor writes in character! This was truly the big moment for T.Swizzle’s pop career IMO and the music video is my favorite of hers – ever. I absolutely love the role playing idea she brings to life with this song and how satirical it is but still brilliantly written – “Me!” is shaking! What a song. A true example of Taylor’s exemplary songwriting craft. Who can write such a song and still make it sound catchy? I don’t think anyone else on earth can as well as she does.

Favorite Moment: “Oh my God, look at that face / You look like my next mistake / Love’s a game, want to play?”

10. “Breathe”

I still have yet to hear Taylor sing this song live despite seeing her live ELEVEN times. This is another example of Taylor’s phenomenal songwriting that ISN’T about a boy! This is actually about the death of a friendship and how you feel like there isn’t really an “ending” when something like that fails. It’s unfortunate because for a lot of situations, relationships – platonic or not, may end for no good reason at all. People simply grow apart and grow up, and it’s an extremely mature topic for then 17-18 year old Taylor to be writing about (the album came out just a couple months before she turned 19).

Favorite Moment:People are people and sometimes it doesn’t work out / Nothing we say is gonna save us from the fall out”

11. “New Romantics”

For an album that was supposed to be heavily influenced by 80s music, there really isn’t THAT much in this realm minus a few songs & “New Romantics” is one of them. I love this synthy, super care free & sassy side we see from Taylor in this song and I think she really could have taken this aesthetic by storm to another level for this album. But she didn’t and I think that’s odd and also very odd that this song was a bonus track. BUT I DIGRESS.

Favorite Moment: We need love, but all we want is danger / We team up, then switch sides like a record changer / the rumors are terrible and cruel/ but honey most of them are true”

12. “Getaway Car”

Let me say one thing first – I can’t believe how many people have asked me about the origin of this song in the past week! The short version is that Taylor went to the Met Gala – I believe alone but still supposedly seeing her then-boyfriend, Calvin Harris, but met Tom Hiddleston and hit it off with him. She also met Joe Alwyn (current boyfriend) the same evening…and eventually ended things with Tom to pursue Joe. The entire song is her admitting to these mistakes..or whatever you want to call them..but describing it in a beautiful 3 minute track of METAPHORS. Your favorite could never! **Think about the place where you first MET me** – get it?

Favorite Moment: It was the great escape, the prison break / The light of freedom on my face, but you weren’t thinkin’ / And I was just drinkin’ / While he was runnin’ after us
/ I was screamin’, “Go, go, go!” / But with three of us, honey, it’s a side show / And a circus ain’t a love story / And now we’re both sorry”

13. “The Lucky One”

I sit here and wonder why all of these songs seem so underrated in the fandom and this one hits me hard too!!!! This track is so specific to Taylor and what I would assume is NOT what she wants her life and legacy to pan out to be…the idea of being forgotten and pushed aside for the next big superstar who’s 20 years younger than you and ready to take your place…it just makes me sad to think Taylor would ever feel that way. I hope she doesn’t just yet.

Favorite Moment: “It was a few years later, I showed up here / And they still tell the legend of how you disappeared, / How you took the money and your dignity, and got the hell out / They say you bought a bunch of land somewhere, / Chose the Rose Garden over Madison Square, / And it took some time, but I understand it now”

14. “Call It What You Want”

I cannot believe there are Taylor Swift fans walking around the earth thinking that Taylor has a better love song than CIWYW. This song is simultaneously about learning to love yourself and loving someone else and that is the most beautiful sentiment ever. It’s about learning to rebuild yourself for yourself and from the support other people giving you and no matter what else happens, that’s completely enough. I can’t think of anything I would want more out of a relationship. I love this song so much!

Favorite Moment: “And I know I make the same mistakes every time /  Bridges burn, I never learn, at least I did one thing right”

15. “Long Live”

I don’t think you can find a Taylor Swift fan who doesn’t love this song and doesn’t have a reason why it means something to them. For me it’s not only such a lovely song about Taylor’s transition into stardom and finding comfort in her family and her band, but it’s also a reminder of all the memories I’ve had in my own life thanks to Taylor and her music. It’s super cheesy but so true! She’s been the soundtrack to my life for over ten years at this point and it means a lot to me.

Favorite Moment: “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 pictures / Please tell them my name”

16. “Forever & Always”

I’m very curious to see if anything on Lover can come to close to Taylor’s best BREAKUP SONG EVER because this one still holds the title for me. I love the pettiness of this track and Taylor’s demand to put it on Fearless just days before the release. There’s something so cathartic about calling out someone’s BS that they spewed to you when you were in a relationship and realizing how messy it was after it ends, and to do it on a public scale…we stan.

Favorite Moment: So here’s to everything coming down to nothing / Here’s to silence, that cuts me to the core / Where is this going? Thought I knew for a minute, but I don’t anymore”

17. “Mine”

Another one that could be considered one of Taylor’s best love songs…I absolutely love how much of a story this song tells and how lovely it was to hear Taylor tell a positive, happy story about love actually working out with someone! I have mixed feelings about Speak Now as an album in its entirety but this song is phenomenal.

Favorite Moment: “You made a rebel of a careless man’s careful daughter” is probably one of my favorite lines she’s ever written.

18. “White Horse”

There comes a time where someone realizes they deserve better and vow to never let someone treat them poorly ever again. This is Taylor’s “White Horse” moment. Such a powerful track from her young age that has stuck with me ever since I heard it for the first time on Fearless. I love how empowering this song makes me feel and now that I think about it – it’s feminist AF!

Favorite Moment: I’m gonna find someone someday who might actually treat me well / This is a big world, that was a small town / There in my rear view mirror disappearing now”

19. “Last Kiss”

If you listened to my podcast episode about my 5 favorite TS songs across each album,  you may remember specifically how EMO I was when I was talking about this song. I personally think this song is on the sad level equivalent to “All Too Well” but isn’t as lyrically striking, which is why it’s lower on my list. It still belongs by the way: not much else makes me more sad than looking back at my “last” moments with someone – whether it’s a friend, romantic interest, event, etc. Looking back and yearning for the past is a feeling of sadness that is often unparalleled to anything else I experience and that’s why I love this song so much.

Favorite Moment: “So I’ll watch your life in pictures like I used to watch you sleep / And I feel you forget me like I used to feel you breathe / And I’ll keep up with our old friends just to ask them how you are / Hope it’s nice where you are”

20. “Wildest Dreams”

I can’t be the only person who constantly wonders what the other person is thinking when a relationship ends, right? While I’m definitely one for overthinking and wondering how things could have ended up differently, or better, or worse…you never really know what the other person is TRULY thinking. And to me, Taylor’s asking that person (dare I say Harry Styles?) to just give her the reassurance that he won’t forget about her even though they both know their time together is over for good. Beautiful but so tragic.

Favorite Moment:  Some day when you leave me / I bet these memories follow you around”

2 are songs from reputation 
5 are songs from 1989
5 are songs from Red
4 are songs from Speak Now 
4 are songs from Fearless
0 are songs from Taylor Swift 

My favorite tracks – 21 through 30. This can change, people:

21. “Wonderland”
22. “Delicate”
23. “King Of My heart”
24. “You Are In Love” 
25. “Dear John”
26.  “Ours” 
27. “I Did Something Bad”
28. “Style”
29. “Fifteen”
30. “All You Had To Do Was Stay”

Who else is as AMPED for Lover as I am?! See you on the other side of release day! I’ll be back soon enough with some thoughts. Click here to see everything I’ve ever written about Taylor Swift.

  • Kristin

Header image photo credit here.

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5 Comments

  1. Sierra A.

    Okay so I am not only super amped for Lover but I also agree with alot of your faves. Its hard for me to put my faves in a particular order, but I am going to try!

    1. Enchanted
    2. This Love
    3. Fearless
    4. You’re Not Sorry
    5. Style
    6. All you Had to Do Was Stay
    7. Dancing With Our Hands Tied
    8. Clean
    9. Back to December
    10. Long Live
    11. Everything Has Changed
    12. King of My Heart
    13. 22
    14. I Wish You Would
    15. How You Get The Girl
    16. Blank Space
    17. Dear John
    18. ME!
    19. So it Goes…
    20. Teardrops on My Guitar

    Like

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