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Taylor Swift’s Top 50 Best Songs of All Time

In honor of Taylor re-releasing "Fearless," it's time to rank her best work to date.
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Let me start this off by saying I know this is probably a bad idea. As a major Taylor Swift fan, my favorite songs change daily. Some days I want to listen to her breakup songs, while other days I’m in the mood for her pop hits. And some days — if I’m really feeling a wide range of emotions — I want to listen to everything at once.

However, in honor of Taylor re-releasing Fearless (complete with previously unreleased songs) on Friday, April 9, I feel it’s my duty as a Swiftie to suck it up and create my list once and for all.

Well, that is until she releases another new album.

Taylor Swift on stage
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After ranking Taylor’s albums less than a year ago, here are my top 50 Taylor songs, ranked from least best to most best (because let’s be honest, she can’t write a bad song). 

50. “I Know Places” — 1989

Many of us won’t understand what it’s like to date someone in the public eye, much less be chased by the paparazzi. Despite the unrelatable premise, the song packs a major punch and is one of the more memorable songs off of 1989.

49. “22” — Red

Turning 22 years old isn’t that exciting, except for the fact you can blast this song all night long and throw double deuces in the air (speaking from personal experience). “22” is not Taylor’s deepest song by any means, but it’s fun, it’s frivolous, and it immediately puts me in a good mood. 

48. “Don’t Blame Me” — reputation 

This is the song I hear in my head when the two love interests in any movie or TV show finally realize they’re meant for each other and kiss. Anyone else?

47. “Cornelia Street” — Lover

“Cornelia Street” is a love song that feels like a breakup song, which threw me for a loop the first few times I listened to it. In the song, Taylor opens up about how she’ll never be able to walk down Cornelia Street again, should she and this person ever break up. Though many of us try not to think about a relationship ending before it ends, Taylor proves with this song that it’s only natural.

46. “White Horse” — Fearless

This song finds Taylor digging into fairy tale tropes, something she did often throughout her first three albums. But, instead of Prince Charming coming to save the day, Taylor’s telling him he’s lost his chance at a happy ending. Better luck next time, bud. 

45. “Mary’s Song (Oh My My My)” — Taylor Swift

Taylor was inspired to write “Mary’s Song” because of her elderly neighbors who fell in love when they were kids. Sure, it’s a tad saccharine, but it’s also incredibly endearing.

44. “Willow” — evermore

“Willow” has to be Taylor’s most experimental lead single to date. Full of weird sounds and interesting phrases, “Willow” feels extremely witchy. And I mean that as a compliment. 

43. “Long Live” — Speak Now

This is Taylor’s love song to the Swifties, the people who’ve stood by her side for 15 years and counting. It’s a stadium anthem that deserves to be heard among thousands of screaming fans.

42. “Hey Stephen” — Fearless

Stephen is one lucky dude. We all dream about our crush writing a song about us, but there’s a good chance it’ll never sound as good as “Hey Stephen,” a song so adorable it hurts. It’s one of Taylor’s most endearing songs, and her little laugh after “and would they write a song for you” is an incredible touch.

41. “Picture to Burn” — Taylor Swift

This song is the epitome of teenage angst. I mean, who among us hasn’t wanted to burn someone’s house to the ground after they’ve wronged us? Just me? OK.

40. “Holy Ground” — Red

A song about looking back on a relationship that came and went, “Holy Ground” makes me want to put on my sneakers right now and run as fast as I can. I don’t know if that’s a compliment, but I’m pretty sure it is.

39. “Forever & Always” — Fearless

Written about her breakup with Joe Jonas, “Forever & Always” is exactly the kind of song I wish I could’ve written about a boy in high school (you know, if I was a songwriter and had talent). It has bite, a little bit of edge, and a whole lot of guitar.

38. “My Tears Ricochet” — folklore

Taylor wrote “My Tears Ricochet” following her public break with her former label, Big Machine Records. Taylor compares the split to a funeral — “If I’m dead to you why are you at the wake?” — which is why it’s her most haunting “breakup” song to date.

37. “Back to December” — Speak Now

Reportedly about her breakup with her Valentine’s Day co-star Taylor Lautner, “Back to December” was Taylor’s first song where she painted herself as the bad guy. It’s a song about regretting your past and wishing you could’ve handled things differently, something I think many of us can relate to.

36. “We Are Never Ever Getting Back Together” — Red

I don’t have to tell you why this song is good, it just is. Dance around to it in your bedroom, blast it in your car, and don’t overthink it. This song isn’t meant to change the way you look at songwriting or relay a deep message about life, it’s just a fun bop about a burned relationship. Sit back, relax, and enjoy.

35. “Call It What You Want” — reputation

After years of worrying about what other people thought of her, “Call It What You Want” is Taylor finally saying “I don’t care what any of you think about me, I’m happy.” Good for you, Taylor.

34. “Delicate” — reputation 

For countless albums, Taylor always felt so sure of herself and her feelings. “Delicate,” on the other hand, is Taylor at her most uncertain. “Is it cool that I said all that? Is it chill that you’re in my head? Cause I know that it’s delicate” is one of her most vulnerable lyrics. 

33. “The Last Great American Dynasty” — folklore

Many of Taylor’s songs could be turned into movies, but this song is an award-winning film waiting to happen. Written about Rebekah Harkness, the woman who built the Rhode Island home Taylor would eventually purchase, this song is storytelling at its finest. Upon first listen, you don’t know why she’s telling us Rebekah’s story until she reveals in the last chorus that she bought the mansion Rebekah lived in.

32. “Shake It Off” — 1989

Prior to releasing “Shake It Off,” Taylor was a country star. Sure, she had put out a few pop-adjacent songs, but she hadn’t fully jumped into the pop pool headfirst. That all changed with “Shake It Off,” a song that has been played at weddings and parties since it was first released in August 2014. It’s pop music in its most basic form, but that doesn’t stop me from getting up and dancing every single time I hear it.

31. “Gold Rush” — evermore

“Gold Rush” is for those of us who spend our time daydreaming about being in a relationship rather than actually being in one (thanks for calling us out, Taylor). Sure, it’s a classic Jack Antonoff production, but it works.

30. “Should’ve Said No” — Taylor Swift

As a classic country breakup anthem, “Should’ve Said No” holds nothing back. It’s direct, cutting, and sends a very clear message — do not mess with Taylor.

29. “August” — folklore

As one-third of the folklore trilogy, “August” is about a teenager who has a summer fling with someone she knows isn’t going to stick around. It feels like summer when I listen to this song, despite its inherent sadness.

28. “Death By A Thousand Cuts” — Lover

Taylor was inspired to write this breakup song after watching Gina Rodriguez’s movie Someone Great on Netflix. Though this song doesn’t come from Taylor’s personal experience, it feels incredibly personal. And that second verse? I don’t know if Taylor’s written anything better.

27. “Out Of The Woods” — 1989

Produced by longtime collaborator Jack Antonoff, “Out Of The Woods” is one of Taylor’s more unique songs. And though the production really stands out in this song, it doesn’t take away from Taylor’s vivid storytelling ability. I see a whole movie in my head when I listen to this song, one full of intense memories, passion, and regret.

26. “Teardrops On My Guitar” — Taylor Swift

This song made me want to have my heart broken by a boy named Drew when I was in middle school, and I still feel that way today. It is teenage heartbreak at its finest.

25. “Red” — Red

Comparing feelings to colors in songwriting is nothing new, but this title track makes me want to air-guitar and head-bang until the sun comes up.

24. “Dear John” — Speak Now

Before there was “All Too Well” there was “Dear John,” one of Taylor’s most heartbreakingly honest songs. Infamously about her failed relationship with John Mayer, Taylor painstakingly details the downfall of their romance. Even if you’ve never had your heartbroken, you can’t help but feel something when listening to this ballad.

23. “Betty” — folklore

Country Taylor is back! “Betty” is the final song of the folklore trilogy (along with “Cardigan” and “August”) about a teenager trying to win back their high school love, Betty. I feel like I’m watching the end of a classic 80s teen movie every time I listen to this song (cue John Cusack holding up a boombox).

22. “Clean” — 1989

Co-written by Imogen Heap, “Clean” compares getting over a relationship with battling addiction. It is also one of Taylor’s most underrated breakup songs. “Ten months sober, I must admit, just because you’re clean, don’t mean you don’t miss it” is a perfect lyric.

21. “Peace” — folklore

Things didn’t work out between Taylor and John Mayer, but the guitar riff on “Peace” feels heavily inspired by Mayer’s work. In the song, Taylor essentially apologizes to her partner for being the biggest pop star in the world. It feels incredibly genuine and it may be one of her most romantic songs to date.

20. “I Knew You Were Trouble” — Red

Who knew Taylor could do dubstep too? “I Knew You Were Trouble” was such a departure from Taylor’s music when it came out in 2012, but it was signaling the path she wanted to go down in the future.

19. “Blank Space” — 1989

After years of being accused of dating men for the sole purpose of writing music, Taylor turned that tired narrative on its head. Full of incredible satirical references, “Blank Space” proved once and for all Taylor knows how to make lemonade out of lemons.

18. “Exile (feat. Bon Iver)” — folklore

I was never the biggest fan of Taylor’s duets in the past (especially with male collaborators), but “Exile” is one of the most mature songs she has ever released. Featuring indie icon Bon Iver, “Exile” is about two people who just aren’t on the same page. Their voices sound incredible together, and the layering of phrases is picture-perfect.

17. “Ivy” — evermore

“Ivy” details a woman who has fallen in love with someone who is not her husband. While it’s sad and heartbreaking in theory, the song itself is incredibly romantic. Put this song on when it’s dark and cloudy outside and don’t tell me you don’t feel something.

16. “Our Song” — Taylor Swift

It’s hard to believe Taylor wrote this song for her ninth-grade talent show, as it’s cemented itself as one of her most memorable tracks. Though she’s a far cry from the country songstress she used to be, “Our Song” makes me long for her banjo days.

15. “Getaway Car” — reputation

For fans who were shocked by reputation’s sound when it came out in 2017, “Getaway Car” felt like it was born out of the 1989 era. About a short-lived romance, reportedly with Tom Hiddleston, the song is chock full of incredible references only true Swifties will understand (“Think about the place where you first met me?” Genius).

14. “New Romantics” — 1989

I honestly don’t even care what this song is about because the melody is next level. Why this song was a bonus track and not on the original album I’ll never understand. If you want to feel like you’re the main character in this thing called life, put on this song.

13. “Love Story” — Fearless

Though “Love Story” is a country song, it was the first taste any of us had of Taylor’s ability to write a genre-bending tune. It’s country, it’s pop, and it was a mega-hit song. Though it’s a re-telling of Romeo & Juliet, albeit with a happy ending, it feels entirely like a Taylor Swift song to its core.

12. “Sparks Fly” — Speak Now

I’m immediately transported to being a 17-year-old whenever I listen to “Sparks Fly.” It’s about as close as Taylor’s going to get to having a rock anthem; therefore, she should be required to play it every time she performs live. Who’s with me?

11. “Treacherous” — Red

Sometimes we do things in life we know won’t end well, but we choose to do them anyway. There are other songs on Red that get more attention, but “Treacherous” is a masterclass in storytelling.

10. “Fifteen” — Fearless

I was 15 years old when “Fifteen” came out, and it is the reason I am writing this article today. I couldn’t believe there was an artist out there who understood my experience of being a young woman in today’s world. Much like re-watching a coming-of-age movie when you’re an adult, I revisit this song often and long for my high school days.

9. “Mean” — Speak Now

This song is for anyone who has ever felt less than for being exactly who they are. Whether you’re in high school dealing with a bully or a full-grown adult having to put up with someone who’s not very nice, “Mean” is the ultimate diss track.

8. “Invisible String” — folklore

Until Taylor released folklore in July 2020, I always believed she was better at writing about heartbreak than love. However, “Invisible String” threw that belief right out the window. In the song, Taylor details all of the things that lead her to her current relationship with actor Joe Alwyn. When I listen to this song, I feel hopeful for the future.

7. “Tim McGraw” — Taylor Swift

Taylor was just 16 years old when she released “Tim McGraw” as her first single way back in 2006. It’s hard to believe she was a sophomore in high school when she wrote this, as the lyrics are incredibly descriptive and vivid. Though young love is fleeting, sometimes all it takes is a song to relive those memories.

6. “Enchanted” — Speak Now

Fairy tales are usually only told in movies and books, but “Enchanted” feels like the closest a song can get. Full of longing and desperation, “Enchanted” perfectly encapsulates that feeling of meeting someone you know is going to change your life.

5. “Wildest Dreams” — 1989

As Taylor’s sultriest song to date, “Wildest Dreams” is most certainly a fan favorite. Written about looking back longingly on a failed relationship, the song makes me want to break up with someone just to listen to “Wildest Dreams” on repeat. This is what Taylor does to me!

4. “You Belong With Me” — Fearless

You Belong With Me” may be Taylor’s most relatable song of all time. Who among us hasn’t had feelings for someone who liked someone else? It’s a tale as old as time, which is why this song will always be a bop.

3. “Cruel Summer” — Lover

Dear Taylor, why was “Cruel Summer” never a single?! This is, without question, her best song off of Lover and one of the best pure pop songs she’s ever written. “Cruel Summer” is all about falling in love with the wrong guy, which in theory should feel terrible. However, Taylor makes it sound like an experience I’m willing to have.

2. “Style” — 1989

This song makes me want to roll down my windows, turn the speakers up to 11, and sing my heart out. Allegedly written about Taylor’s past relationship with Harry Styles (hence the title), “Style” is full of ‘80s influences and is one of the singer’s more sultry hits.

1. “All Too Well” — Red

What can I say about “All Too Well” that hasn’t already been said a thousand times? This song is a certifiable masterpiece. “All Too Well” is to Taylor Swift what “Landslide” is to Fleetwood Mac. Sorry, it’s just the truth!

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