Taylor Swift is no stranger to making songs that easily bring tears to our eyes. Her storytelling can hit just a bit too close to home sometimes. There are many songs by Taylor that could possibly make you cry, and I mean MANY, but this list is the top 10 Taylor songs that I personally can't listen to without sobbing. Let's see if you agree!
Looking for the saddest songs that are specifically related to breakups?
Read our Top 13 Saddest Taylor Swift Breakup Songs article!
10. Fifteen
"I found time can heal most anything, and you just might find who you're supposed to be". They say Taylor Swift has a song for everybody, and out of any of her songs, Fifteen would be the one the majority of people can relate to. We've all been young a naïve, thinking you know everything when you don't, and experiencing hurt and heartbreak for the first time like you never have before. Sometimes the emotion of listening to this song doesn't come from the hurt you experienced when you were younger, but the realization of where you are now. You made it through, and you're still here.
9. All Too Well
"I'd like to be my old self again, but I'm still tryin' to find it." I'm going to clump together All Too Well and the 10 minute version, because they're both incredible and genius in their own way. All Too Well is known for being a fan favorite and there's a reason why. The lyrics are written in such a way that you are able to put yourself into the song, almost like it's something that has happened to you. The story-telling is so incredible that you can't help but tear up, especially if you've been through a similar situation that Taylor has when she wrote this song.
8. Tolerate It
"Gain the weight of you then lose it, believe me I could do it." Let's be honest, Taylor is the queen of writing break up songs. If you're ever going through a break up, Taylor's discography can get you through it. 'tolerate it' describes being in a relationship that you almost feel trapped in. They're not the same person they were when you met them, but you still feel love for them. You're trying to gain the courage to leave them or at least confront them about how they're making you feel lately. The bridge in this song gets me every time.
7. Never Grow Up
"It's so much colder than I thought it would be, so I tuck myself in and turn my night light on". Forgive me, there is not a Taylor's Version of this song yet, but it's 100% belongs on this list. Along with 'Fifteen', I'd say 'Never Grow Up' is up there with the most relatable songs by Taylor Swift. We all have the experience of growing up, being terrified to do "grown up" things and going into the world on our own for the first time. Some of us would do anything to be a kid again, just to have one day with no real responsibilities or stress. If you feel this way, 'Never Grow Up' is a guaranteed cry fest for you.
6. Marjorie
"I should've asked you questions, I should've asked you how to be." Losing a grandparent is one of the hardest life experiences to go through, especially when they were your best friend. You get such a short time with them but it's some of the best memories you'll ever have. Taylor wrote 'Marjorie' for her own grandmother, but many can relate to losing someone that was super close to you. It's bittersweet to reminisce on the times you had with them, but then you're thinking about the "what if" of it all. What could you have done better to make your time with them even more fulfilling. The bridge in this song is tough to listen to without getting choked up, but what gets me even more is hearing Marjorie singing opera in the background of the outro.
5. Bigger Than The Whole Sky
"I'm never gonna meet what could've been, would've been, what should've been you." There's a couple different ways that fans have interpreted this song. Some believe it's about losing a baby, some believe it's about losing yourself after a traumatic event. But no matter how you interpret the song, it has it's own special meaning for each person who listens to it. That's what so special about Taylor's writing, is it doesn't have to mean one specific thing; it can mean many different things. So whatever your meaning of this song is, it's bound to make you emotional. From her soft spoken vocals and the heavenly music, it's hard to keep yourself together while listening.
4. Would've, Could've, Should've
"God rest my soul, I miss who I used to be." In a similar situation as 'All Too Well' - 'Would've, Could've, Should've' is the fan favorite song off of Taylor's 'Midnights' album. Though it may never become a single in the way 'All Too Well' did, Swifties are making sure this song doesn't go unnoticed. Unfortunately, a lot of us can relate to having a relationship that changed who we are forever. Even years down the line, we face challenges in our minds that wouldn't be there if it wasn't for the traumatic experience of being taken advantage of by someone you were supposed to trust. Listening to the repetition of the bridge at the end of this song is almost like an outer body experience.
3. Forever Winter
"Too young to know it gets better / I'll be Summer sun for you forever." Now we are in the territory of "If I listen to this song, I'm emotionally done for the rest of the day". Mental Health is one of the biggest ignored issues in society today. Whether 'Forever Winter' is reminding you of yourself or someone you care about, it hits you really hard. Don't let the instrumentation trick you! It's the perfect definition of a juxtaposition, where the music sounds happy but the lyrics are very sad and emotional.
2. Soon You'll Get Better
"Who I am supposed to talk to? What am I supposed to do, if there's no you?." 'Soon You'll Get Better' is a song that I avoid listening to a lot. Don't get me wrong, it's an incredible song and it's written beautifully, but I can't even get through the first verse without crying. Taylor wrote 'Soon You'll Get Better' about how she felt when her mom was going through cancer treatment. As someone who has lost somebody to cancer, this song is almost unbearable to listen to for my emotional sake. Taylor actually said she planned on never performing 'Soon You'll Get Better' live because it was too difficult for her emotionally, but once the pandemic started she blessed the world with her charity performance at Global Citizen.
1. Ronan
"Flowers pile up in the worst way, no one knows what to say about a beautiful boy who died." Similar to 'Soon You'll Get Better', 'Ronan' is nearly impossible to listen too. Agreeably one of Taylor's saddest songs of all time, Ronan Thompson was a little boy who lost his battle to cancer. Taylor wrote the song in the perspective of Ronan's mom, Maya, in which Taylor felt personally impacted by Maya's story of Ronan online. If you've never heard this song before, please let me warn you - go grab your tissues and give yourself the rest of the day to eat ice cream in bed.
Did any of these songs make you cry? Do you disagree with this list, or feel another song should've been included? Visit our Instagram below and let us know!
Written By: Kaitlyn Nicole
*copyright not intended. Fair use act, section 107.