I can quite honestly say that finding enough songs to fill a saddest Taylor Swift songs playlist couldn’t be easier. Let’s face it; there are plenty since she’s pretty much made a career out of this kind of thing. What is a little trickier, though, is trying to cut the list down to a manageable number.
However, that’s what I’ve done. I hope you find one or two of your favorite sad Taylor Swift songs among them. I also hope you enjoy revisiting them as much as I enjoyed putting together the list. So, let’s get to it and take a look at the first song…
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Top 7 Saddest Taylor Swift Songs
All Too Well
It is a tough task to know where to start. But I’ve got to start somewhere, so I’ve started with my favorite sad song written by Taylor Swift.
What do I like about it?
I mostly like the great balance between Folk and Country. Additionally, I like the fact that there are plenty of dynamics that keep the song interesting right until the end. Plus, despite some of the sections including a full band, Taylor Swift’s guitar playing remains central and is never overwhelmed.
There was a big production crew on the single, but they didn’t make the mistake of overproducing the final product. This could have been because Taylor Swift was on the production team. She’s a class act and understands that less all too often is more.
“All Too Well” came out in 2012 as a single from the phenomenally successful album Red. When it was released, the song made it to the top of the Billboard charts and was her eighth single to make it there.
Red was as equally successful…
It went to #1 on pretty much every Country chart you can think of and also on the mainstream charts in several countries. It went seven times platinum in the US and also formed the backbone of her subsequent tour, which netted her an astounding $150 million.
That made it the most successful Country tour in history. I bet that kept her in cat food for a while.
So, what’s this fantastic song all about?
Not surprisingly, it is about a past boyfriend who behaved less than perfectly. It is a pity fest that dwells on all the good memories and then the inevitable pain and heartache. The thing is, by a quick delve into the lyrics, you can see that the guy wasn’t interested.
Taylor, you need to up your game and start picking your men a lot better. Let’s move on and see if she learned from her mistakes.
Exile
This was released in 2020 and is likely the last of the saddest Taylor Swift songs she’s released. When it came out, most of Taylor’s love woes looked well and truly behind her. “Exile” was, therefore, written drawing on past experiences.
Indeed, at this point, it was something she had been doing for quite a while. The fact is that she had already been in a happy relationship with Joe Alywn for four years. And, as I write this, I’m pleased to say that they are still together. I hope it continues and they have a great future together.
Back to the song…
“Exile” is written from both a male and female perspective. She sang from a woman’s point of view, and the male part was sung by Justin Vernon, the lead singer of Bon Iver.
The song is a heartbreaking account of a guy who has recently split from his girlfriend and happens to bump into her a short time later.
She is with another man, and he is upset that she has moved on so quickly, as he felt the split was initiated by her. He obviously still has feelings for her and hasn’t moved on.
On the other hand…
She is angry at him for not allowing her to get on with her life. She feels he’s being hostile to her new boyfriend and should let things go. From her perspective, he had plenty of chances to keep the relationship together but never took them.
In the chorus, it’s clear that they still have feelings for each other, but she does want to reconcile. It sounds like they should have just sat down more and talked to each other when they had the opportunity. Oh well!
The single got to #6 in the US and #8 in the UK. It was also nominated for a Grammy. The album it was taken from, Folklore, made it to the top spot in the US and the UK, as well as several other countries. It received widespread critical acclaim and won a Grammy for Album of the Year.
Dear John
We’re going back to 2010 when “Dear John” was released from her third album, Speak Now. This sad Taylor Swift song made it to #54 on the Billboard US charts.
The album was altogether much more successful from a commercial perspective. It made it to #1 in the US, and the first week alone sold an incredible million copies.
Musically, it’s a beautiful Country/Folk song that plays perfectly to all of Taylor’s strengths. It features stripped-back acoustic guitar playing that crescendos at the chorus. This allows Taylor to change things up and deliver a very powerful vocal performance.
Lyrically, things have not gone well for the singer…
It’s about her being in a relationship where she never felt settled. Things went from good to bad at the drop of a hat.
She couldn’t work the other person out and felt like she was constantly locked in something like a chess game. She had feelings for the guy but felt like this was never truly reciprocated. Ultimately, she had to get out of the relationship to avoid being hurt.
Many have figured that this is about her relationship with John Mayor. This could well be the case, as John Mayor has even commented on the song as being “cheap songwriting.” This is presumably at his expense if we are to believe it’s about him. Regardless, it’s a great song.
White Horse
We’re stepping back another few years here because the song was released on the 8th of December when she was just 18 years old. However, it was written in 2006 when she was just 16. Frankly, that’s nothing short of incredible.
How can you write something this good when so young?
“White Horse” wasn’t even her first song. It was the second single off her second album, Fearless. By this time, she already had a growing fan base, and they went out in force to buy it. Total sales topped two million in the US alone.
Not only did the buying public love it, but the critics loved it too. It won a handful of awards, including two Grammys. One for Best Country Song and one for Best Female Country Performance.
The album didn’t do too badly, either…
That got to #1 on the US Country charts, of course, but also made it to #1 on the US Billboard charts. More impressively, it sold a cool 12 million copies. Not bad for a teenager.
The song is essentially about the realization that fairy tales are just that. It is almost like a coming-of-age song where the girl has to confront the uncomfortable truth that falling in love might not be as it seems in the movies and TV.
The knight in shining armor and riding the white horse was never coming. Instead, we got a widely popular sad Taylor Swift song.
Betty
This is quite unusual when compared to most of Taylor Swift’s other songs. That’s because it’s told from the perspective of the man.
Generally speaking, most of her songs are from the female’s perspective. Very often, they are from her viewpoint and her own experiences, even if they are sometimes disguised as such.
Isn’t that right, Mr. John Mayor?
“Betty” was released in 2020 from the album, Folklore, which I’ve already talked about when I looked at her single “Exile.” “Betty” performed best on the Country Charts, making it to #6, which given that it is through and through Country, is hardly surprising.
However, on most main charts around the world, it failed to make it into the Top 20. I think it is a better song than the sales and charts positions would indicate. I can’t help thinking that it might be because of the change of narrative to a man.
So many of her fans identify with Taylor, and most are female, that perhaps it’s a song they just couldn’t fully relate with.
So, what is it about?
It’s about a teenage boy, James, who cheats on his girlfriend. He is subsequently remorseful and wants to make it up to her. He now wants to know if he would still have a chance of getting back together.
James tries to blame his infidelity on his youth and that it is just a stupid mistake. It is not clear what the answer is, but if she has any sense, she will tell him to go… away! Not quite what I wanted to write, but you get the idea.
Teardrops on my Guitar
This is the second song that Taylor ever released. But it is the first of the saddest Taylor Swift songs in a very long line.
Her debut song, also released in 2007, was “Tim McGraw,” but that didn’t make my list. That’s because, although it was about a past relationship (no surprise), it was more nostalgic rather than a sad commentary.
“Teardrops on my Guitar” charted higher and sold more copies than her debut single. It got to #2 on the US Country charts and #13 on the Billboard top 100. Also, it sold over three million copies.
It received a lot of critical acclaim too…
And it won three awards, including a BMI Pop and Country award. It was taken from her debut album, Taylor Swift, which was released a year earlier in 2006, when she was just 16 years old. The album went on to sell over seven million copies globally.
“Teardrops on my Guitar” is mostly a Country song, though it contains Pop elements too. It’s a nicely mixed song that is not heavily produced and allows the pain and humanity of the song to shine.
It’s a story of unrequited love in high school…
Given the age of Taylor when she wrote the song, that kind of makes sense. She sings about how she has to watch on as her crush goes out with someone else. To add salt to the wound, he confides in her about his feelings for the other girl.
The singer is now in the friend zone and has to take solace with her guitar and cats. I bet that bloke is kicking himself now.
Breathe
This is our last of the saddest songs by Taylor Swift and another from the hugely popular album, Fearless. It was released in 2008 and was co-written with the amazing singer-songwriter Colbie Calliat.
Colbie also featured on the song and put in a masterful backup vocal performance alongside Taylor. Their blend of voices worked beautifully to create a wonderful song.
“Breathe” was recorded in Tennessee and has pure Country running through its veins. The acoustic guitar remains prominent throughout the song, with a mandolin sometimes joining in. There’s also the light use of violins and a piano, though only occasionally.
Unlike nearly every other song about a relationship that Taylor has recorded…
This is about friends rather than lovers. It is a story of having to say goodbye to a friend, though apparently, there’s no fault on either side.
I honestly don’t get this at all. I understand when it’s a relationship between a couple, but between friends, I don’t see it. When no one is to blame, why does it have to end?
For whatever reason, it made good sense to Taylor. So, she does what she always does. Writes a song about it, has a good cry, records a song, and makes a shit full of money. Good for her.
Looking for More Sad Songs?
Well, take a look at our comprehensive articles on the Best Sad Songs, the Top Songs About Jealousy, the Best Songs About Depression, the Top Songs About Unrequited Love, and the Saddest Kanye West Songs for more emotional song selections.
Also, you’ll need to listen to those tunes. So, check out our in-depth reviews of the Best Headphones for Music, the Best Sound Quality Earbuds, the Most Comfortable Headphones, the Best True Wireless Earbuds, and the Best Headphones Under $200 you can buy in 2023.
Saddest Taylor Swift Songs – Final Thoughts
So, there you have it. This has been fun, and I can also say that happily, it might be possible that Taylor Swift’s saddest songs are now well and truly behind her. I say this because she now looks on the verge of marriage and hopefully long-term happiness.
As much as we joke about her making lemonade out of her previous failed relationships, it would be nice for her to stop. She’s now thankfully running on memories stretching ever further back, and it is time to let go. Start writing about happy stuff, Taylor, and I promise we’ll still love you.
Until next time, happy listening.
