Top 30+ Saddest Taylor Swift Songs [2023 Updated]

1 All Too Well

It is a challenging task to know where to start, as I’ve started somewhere with my favorite sad song written by Taylor Swift.

What are the things that I appreciate about it?

I mostly enjoy a great balance between Country and Folk music. Additionally, I like the fact that there are plenty of dynamics in the interesting song, which keeps me engaged until the very end. Plus, despite the inclusion of sections with a full band, Taylor Swift’s guitar playing remains central and I never feel overwhelmed.

She often understands and acts as a class A team member. This could have been because of Taylor Swift’s presence in the production team. They did not make the mistake of overproducing the final product, but there was a large production crew working on it.

In 2012, when the Red album was released, the song “Well Too All” came out as a single and made it to the top of the Billboard charts, becoming phenomenally successful.

Red was as equally successful as blue in the competition.Output: Red was just as successful as blue in the competition.

A remarkable $150 million, which earned her, served as the foundation of her subsequent tour, achieved seven times platinum status in the US and also on the popular charts in various countries. It reached the top position on almost every Country chart you can imagine.

That made it the most successful Country tour in history. I wager that kept her in feline nourishment for a while.

So, what’s this amazing song about?

The man lacked interest, evident through a brief exploration of the lyrics. The unavoidable suffering and emotional distress, followed by the lingering fond memories, create a pitiful gathering. It is not surprising that he has a less than ideal boyfriend, considering his troubled history.

Taylor, it would be better if you start picking a lot of men and you need to step up your game. Let’s see if she has learned from her mistakes and move on.


2 Exile

This was released in 2020 and is likely the final of the most melancholic Taylor Swift songs she has published. It emerged when, after her truly and deeply felt romantic troubles, Taylor’s love for music was at its peak. “Exile” was therefore written based on previous personal encounters.

They have a great future together and I hope it continues. I’m pleased to say that they are still together as I write this. The fact is that she had already been in a happy relationship with Alywn Joe for four years. Indeed, she had been doing something for quite a while at this point.

Returning to the song….

“Exile” is written from the perspectives of both a man and a woman. The female perspective is conveyed through her singing, whereas Justin Vernon, the lead singer of Bon Iver, performs the male part.

The song is a heartbreaking account of a guy who recently split from his girlfriend, after a short period of time, due to a bump they had.

It is evident that he still harbors emotions for her and has not progressed, as he perceived the breakup to be instigated by her and he is distressed by the fact that she has moved on hastily. She is currently in a relationship with another man.


He had plenty of opportunities to keep their relationship together, from her perspective. He feels hostile towards her new boyfriend and thinks he should let things go. She is angry at him for not allowing her to get on with her life.

Well, in hindsight, it would have been beneficial if they had taken more time to sit down and engage in conversation. However, it is evident from the chorus that she desires to mend their relationship, indicating that they both still harbor emotions for one another.

The album Folklore won the Grammy for Album of the Year and received widespread critical acclaim. It also made it to the top spot in several other countries, as well as the UK and the US. The album was taken from Folklore. It was also nominated for a Grammy. The single The got to #8 in the UK and #6 in the US.


3 Dear John

“Dear John,” a melancholic song by Taylor Swift, reached the 54th position on the Billboard US charts upon its release from her third album, Speak Now, in 2010.

The album sold an astonishing one million copies in its first week alone and reached the number one spot in the US. From a commercial standpoint, the album was much more successful overall.

This allows Taylor to change things up and deliver a very powerful vocal performance. The chorus features crescendos at which Taylor plays the acoustic guitar in a stripped-back manner. It’s a beautiful Folk/Country song that musically showcases all of Taylor’s strengths.

In terms of lyrics, things have not gone smoothly for the vocalist….

At the drop of a hat, things went from good to bad. She never felt settled in a relationship. It’s about her.

She had to get out of the relationship, ultimately, to avoid being hurt. Although she never truly reciprocated these feelings, she had feelings for the guy. She felt like she was constantly locked in a chess game, but she couldn’t make the other person work out.

It’s an excellent tune, regardless. If we are to assume it’s about him, this is likely at his cost. John Mayor has even remarked on the song as being “inexpensive songwriting,” which might indeed be true. Numerous individuals have deduced that this relates to her connection with John Mayor.


4 White Horse

It’s amazing how little there was to say about her in 2006, when she was just 16 years old. Another few years have passed since then, and we’re taking a step back here because the song was released on December 8th, when she was only 18 years old.

How can you compose something this impressive when so youthful?

They went out to buy it, forcing total sales to top two million in the US alone. By this time, she already had a growing fan base. Even her first single off her second album, “White Horse,” wasn’t her second song off Fearless.

It received recognition for Outstanding Female Country Performance and one for Outstanding Country Song. It garnered several accolades, including two Grammys. Not only did it receive acclaim from critics, but it also resonated with the purchasing audience.

The album also didn’t perform poorly….

A adolescent, not too shabby. It sold a remarkable 12 million copies, even more impressively, it reached the top spot on the US Billboard charts but also achieved the #1 position on the US Country charts.

The girl in the movie and TV appears to be experiencing an uncomfortable truth about falling in love, similar to a coming-of-age song. Essentially, the song is just about fairy tales.

However, what we received was a highly beloved melancholic Taylor Swift tune. The brave and gallant hero mounted on a majestic white steed would never arrive.


5 Betty

The viewpoint of the man is narrated because in contrast to most of Taylor Swift’s other songs, this is rather uncommon.

Most of her songs reflect the female’s perspective. Sometimes, they are disguised, but they often express her own experiences and point of view. In general,

Isn’t that correct, Mr. John Mayor?

Not particularly unexpected, considering that it is unmistakably a Country song. Ranking at #6 on the Country Charts, “Betty” had the highest performance. Upon examining her track “Exile,” which I have previously discussed, it became evident that “Betty” was released in 2020 as part of the album, Folklore.

I can’t help thinking that it might be the man’s narrative of change. I can’t help thinking that the song is better than the sales charts and positions would indicate. However, it failed to make it into the top 20 on most of the main charts around the world.

Many fans of Taylor Swift, who are mostly female, can fully relate to that song because they couldn’t just identify with it, but also feel a deep connection with it.

So, what is it all about?

After breaking up, he is now curious to know if he still stands a chance. He desires to reconcile with her and feels regretful. The focus of this story is a teenage boy named James, who is unfaithful to his girlfriend.

James tries to blame his infidelity on his youth, but it is not clear what the answer is if she has any sense to tell him to go away, what I wanted to write but quite not what I wanted to get the idea. It is just a stupid mistake.


6 Teardrops on my Guitar

This is the saddest Taylor Swift song ever released, and it is the second song in her first album.

The commentary on the past relationship was more nostalgic than sad, as it was a surprise. Although I didn’t make a list, it was Tim McGraw, her debut song released in 2007.

It sold over three million copies. Additionally, it reached #13 on the top Billboard charts and #2 on the US Country charts. Her debut single “Teardrops on My Guitar” charted higher and sold more copies.

It also received a great deal of critical praise….

The album, which was released in 2006, went on to sell over seven million copies globally. It was taken from Taylor Swift’s debut album, which she released when she was just 16 years old. It won three awards, including a Country and Pop BMI award.

“My song, Guitar on Teardrops, is mostly a Country song, although it contains elements of Pop. It allows humanity and pain to shine through the song, and it’s not heavily produced.

It is a tale of unreciprocated affection during the high school years…

It is logical, considering Taylor’s young age when she composed the song. When her crush starts dating someone else, she is forced to witness it, and she expresses her emotions through her singing. To make matters worse, he confides in her about his feelings for the other girl, further exacerbating her pain.

Currently, the singer finds himself trapped in the friend zone and seeks comfort in playing her guitar and spending time with her cats. I’m certain that guy is feeling quite frustrated at the moment.


7 Breathe


This is the last of our saddest songs, co-written and released in 2008 by the amazing singer-songwriter Colbie Calliat. It came from the hugely popular Fearless album by Taylor Swift.

The voices of Taylor and Colbie beautifully blend together to create a wonderful song. Taylor’s masterful vocal performance is showcased alongside the backup vocals, making the song even more captivating.

Sometimes, only on certain occasions, the light and delicate sounds of piano and violins are also utilized. However, the acoustic guitar remains prominently featured throughout the song, occasionally joined by the addition of a mandolin. “Breathe” was recorded in Tennessee and possesses a pure Country essence flowing through its veins.

In contrast to almost every other song about a romantic connection that Taylor has recorded…

This is apparently a story of saying goodbye to a friend, although there seems to be no fault on either side. This is more about being friends than being lovers.

Why does it have to end? There is no blame when one does not see it. I don’t see it, but I understand the relationship between friends when it’s a couple. Honestly, I don’t get it all at this.

She, for good. Money of complete nonsense creates and records a song, has a great emotional impact, and always writes a song about what she truly feels. Whatever the reason may be, it always makes sense to Taylor.

8 Ronan


9 I Almost Do


10 Come Back, Be Here


11 The Archer


12 Last Kiss


13 Illicit Affairs


14 The Last Time


15 Cold As You


16 Sad Beautiful Tragic


17 The Moment I Knew


18 Come In With the Rain


19 This Love


20 New Year’s Day


21 Never Grow Up


22 Clean


23 Red


24 Forever and Always


25 Speak Now


26 I Wish You Would


27 Long Live


28 Back to December


29 Tied Together With a Smile


30 You Belong With Me


31 State of Grace


Looking for More Sad Songs?

Our comprehensive articles offer a wide range of emotional song choices for the Saddest Kanye West Songs, the Top Songs About Unrequited Love, the Best Songs About Depression, the Top Songs About Jealousy, and the Best Sad Songs. Feel free to browse through them.

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Saddest Taylor Swift Songs – Final Thoughts

I hope Taylor Swift’s happiness and marriage will last for a long time. It seems like she is on the brink of achieving this, I must say. Those saddest songs of Taylor Swift’s are now truly behind her, and it is possible that you might have them there. This has been a fun experience, and I can also happily say that.

Taylor and I promise to continue loving each other. We are happy to start writing about the time when our memories stretch back even further. We are grateful that she is now in a better place. It would be nice to stop and appreciate how she has turned her previous failed relationships into a joke, making lemonade out of lemons.

Until we meet again, enjoy your listening.