Taylor Swift Songs Bracket

I had seen this going around Twitter earlier this week and my good blog pal Paul sent it to me. So I figured I might as well do it. That means I spent a half hour the other night filling it out, and boy was it stressful.

I’ve been a Taylor Swift fan since high school, so we’re talking like 10 years. I don’t follow her super closely but I’ve listened to mostly all of her music. I knew 95% of the songs in the bracket and had to look up a few; they were her older songs.

As you can see, there are 64 songs to start with, so I’m not going to post all of them. But I’ll start with the Sweet 16:

  • Miss Americana vs. The Story of Us: I do Like “Miss Americana” but “The Story of Us” is such a throwback for me.
  • Endgame vs. Long Live: “Long Live” is my favorite Taylor Swift song ever, so…
  • Out of the Woods vs. Dear John: “Dear John” is also a throwback from her Speak Now album that still gets me.
  • You’re Not Sorry vs. Back to December: Same with “Back to December”.
  • I Knew You Were Trouble vs. Wildest Dreams: I’d listen to “Wildest Dreams” over “I Knew You Were Trouble” if I had the choice.
  • All Too Well vs. Delicate: Ugh. “All Too Well” makes me cry.
  • Begin Again vs. State of Grace: It was so hard to pick between these two songs. They remind me so much of my freshman year of college (but really, the entire Red album is my freshman year of college), and they both still get me. I listened to both of them as I did this, and “State of Grace” just hit me a little bit more.
  • The Man vs. Red: I do really like “The Man” but “Red” is another one of those throwbacks. As soon as I hear the first few notes, I know 100% that it’s “Red”.

Elite 8

  • The Story of Us vs. Long Live: “Long Live” it is.
  • Dear John vs. Back to December: This was one of a few really hard picks. I listened to each of the songs and tried to pick which one I liked a little bit better. The winner was “Back to December”.
  • Wildest Dreams vs. All Too Well: “All Too Well” all the way.
  • State of Grace vs. Red: This was another really hard one. They both mean a lot to me, but I decided to go with “Red”.

Final 4

  • Long Live vs. Back to December: I do like “Back to December” but it’s gonna have to be “Long Live”.
  • All Too Well vs. Red: Another really hard pick. I listened to both songs to compare, and it was “All Too Well”.

Final match-up

  • Long Live vs. All Too Well: This was tough. Yes, “All Too Well” makes me cry, but it’s always going to be “Long Live”. Always. I associate it with my time as manager for my high school’s varsity baseball team, which was one of the best things I ever did. I did an art project in high school and I painted some of the lyrics on a canvas; it’s still hanging up in my room.

I also added a few songs that didn’t make the bracket but are ones I really like: “Enchanted,” “Holy Ground,” “Call It Want You Want,” and “I Think He Knows.”

If you have the time, fill out the bracket! I think it’ll only work if you know most of her songs, soooo.


  1. This was a really cool breakdown. I’d fill it out, but I haven’t heard enough of her songs. Out of your Elite 8, I’d only heard one of them. When did she find the time to write all these songs??

    Liked by 1 person

  2. This is so fun!!! Taylor Swift has so many good songs, so this would be hard! Fearless was my favorite album. I am pretty sure I got the CD for my 13th birthday haha. Hope you are doing well 🙂

    Liked by 1 person

  3. This is such a cool bracket; I might give this a try! I think I was in middle school when I started listening to her music. I haven’t listened to her latest album as much as the others so I’m not familiar with “I Think He Knows,” but “Enchanted,” “Call It What You Want,” and “Holy Ground are some of my faves too!

    Liked by 1 person

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