Taylor Swift's Top 10 Most Heartbreaking Anthems

(Sorry I had to do this to you) 

You’re missing a friend. Did badly on an exam. Broke a promise. Spilled a secret you shouldn’t have. Got in a fight with your mom. Embarrassed yourself in front of your crush. Accidentally stepped on your dog while walking to the fridge. Or, perhaps the most prevalent of cases, you’re experiencing the heart wrenching pain of a breakup (men are trash).   

You trudge to your room, snuggle up in your bed, and ever so dreadfully tug your headphones on and navigate your way to good ole Spotify. On a scale of one to ten, you’re currently feeling somewhere around a negative seven. In this moment, what artist are you choosing to listen to? I think we all know the answer to this one. Queue the Red deluxe album, stat.  

I give you: Taylor Swift’s Top Ten Most Heartbreaking Anthems. Prepare yourself while you can. My apologies in advance.  


  1. 1. "Death by a Thousand Cuts"

    Let’s start here and progressively get more and more painful because I feel like that’s the most traumatizing--scratch that--  right way to do this. “Death by a Thousand Cuts” is from Swift’s newest album, Lover. This song definitely projects a different sound compared to Swift’s older melancholy melodies. Even though I’m sure Taylor’s inspiration came from a place of true love and years of history, the lyrics took me back to freshman year when I would agonize over Brad from fratland that I’d met a week before. I mean, the song is what you make of it. Second verse: “but if the story’s over, why am I still writing pages?” That hits. We could have had it all, Brad.  

  2. 2. "Wildest Dreams"

    In my opinion, 1989 is my least favorite album by Swift (fight me) but “Wildest Dreams” is a masterpiece that never fails to make me teary-eyed. For reference, I’m a Leo with a Capricorn moon-- tears don’t come easily. This song has a wistful, nostalgic, almost homesick sense in both words and sound. I think Swift perfectly delineates the fear of being forgotten in this song.  



  3. 3. "Sad Beautiful Tragic" 

    Unfortunately for me, I cannot listen to this song without thinking about the boy I met on a Friday night at the Jersey Shore, summer 2016. I barely knew him but thanks to this song I’ll never forget him. Pitiful. I needed a hobby. This song from Swift’s Red album does an impeccable job of explaining itself within the title. Sad, beautiful, and tragic. It is slow and somber, perfect for grieving over a 16 year-old boy that isn’t worth your time and/or failed his permit test not once, but twice. Not that I would know.  


  4. 4. "Treacherous"

    Now we’re getting to the good stuff. “Treacherous” is a classic tune from Red that perfectly embodies the feelings caught in the early stages of talking to a new interest. Overwhelming, nerve-wracking, uncertain, exciting. Ah, yes, the anxieties of new relations. If you listen closely it is fair to say these lyrics are nothing short of celestial. "Treacherous” also just goes to show that even Taylor Swift craves emotionally unavailable men with trust/commitment/too many issues. As she says in this song, “nothing safe is worth the drive,” note taken.  


  5. 5. "You're Not Sorry"

    No, he's not. They never are. Moving on. 

  6. 6. "Clean"

    You can stop thinking about your idiot ex for a slight second because I think “Clean” is more about self-reflection rather than men and their ever-so-wonderful way of being. Swift considers the changes that occurred after ending a previous relationship. She says, “when I was drowning, that’s when I could finally breathe.” This song is undoubtedly one of the artist’s more perceptive works, relaying hidden meanings and powerful imagery. It captures both emotional struggle and relief. 

  7. 7. "Dear John"

    “Dear John” is six minutes and forty-five seconds of indescribable pain. There’s clearly a lot of history behind this song. Swift holds nothing back in regards to voicing her feelings towards her ex. 


  8. 8. "Back to December" 

    If you’re going through a breakup this is maybe the first or second song you queue up while downing in a pint of ice cream. No judgement here. “Back to December” embodies the thoughts that cross our minds when we’re watching movies...alone in bed and suddenly missing our SOs...understandable.  


  9. 9. "Last Kiss" 

    I don’t know about you but I think I can actually feel the pain coursing through my veins when I listen to this song. If I’m found listening to this song my roommates know that an intervention is needed along with my warmest blanket and a tray of brownies delivered to my bedside. “All that I know is I don’t know how to be something you miss.” How am I supposed to be okay after that?  



  10. 10. "All Too Well" 

    There’s really not much I can say here. I’m not going to try and describe the greatest masterpiece of our generation because it is hands-down inexplicable. Taylor Swift is known as one of, if not the greatest songwriter of our generation and this might be her best lyrical work that we have seen so far. All I can say is, if you really want to get in your feels, go on a nighttime drive by yourself, play this song, and sing at the top of your lungs. It’s basically free therapy.  


This ranking was not easy nor was it necessarily healthy for my well-being. Just for convenience I made a Spotify playlist with all of the songs. Happy listening!