41 Sad Taylor Swift Songs: Saddest T-Swift Tracks

Taylor Swift is one of the best songwriters of our generation and a magician when it comes to making her listeners feel something. Whether that be joy and happiness or heartbreak and sadness, she is a master of crafting songs relatable to fans and the perfect outlet for emotions.

She always brings her personal experiences into the tracks, making her even more loved by fans as it makes it easier to get to know the woman behind the music. Here are the 41 saddest songs of Taylor Swift’s career that are likely to bring a tear to your eye. 

1. Ronan (Taylor’s Version)

Taylor Swift - Ronan (Taylor's Version) (Lyric Video)

There’s honestly not a more sad thing in life than cancer in children, so it should come as no surprise that this song ended up being at the top of our list. Ronan was a tribute by Swift to a young boy named Ronan who lost his battle with cancer at the age of four. Her songwriting skills are also on full display, allowing her to capture the absolute devastation felt by the young boy’s family in the wake of his loss.

Unlike some of her other songs, the instrumentation in the track is fairly simplistic, but it lacks none of the emotion you expect from such a heavy topic. She sings about his life and—gently—crafts a poetic tale of an incredibly tragic scenario.

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2. All too Well

Taylor Swift - All Too Well: The Short Film

All Too Well would likely be the top song on our list had Ronan not touched a special nerve in my brain. A heartbreaking ballad from her Red album, it discusses one of her past relationships that still haunts her years later.

The track is essentially her reopening old wounds—or scars that never healed up. It ended badly and there wasn’t anything she could find about it that was redeemable. Above all of her other songs, the poignancy and clarity of her lyrics pull on your heartstrings and allow you to understand just how deeply she was affected by the incidents.

3. Would’ve, Could’ve, Should’ve

Taylor Swift - Would've, Could've, Should've (Official Lyric Video)

Would’ve, Could’ve, Should’ve is easily one of Swift’s most complex and sad songs. It’s a long reflection on a past relationship, going over all the things she and the other person could have done to make things work. It gives you a glimpse of the possibilities that never came to be, pondering all of the what-ifs that could have been a reality had things not gone wrong.

It continues to build throughout the track, both in the instrumental and in the weight of her lyrics. It’s one of her most powerful introspective songs and easily one of the most emotional tracks she’s produced. 

4. Dear John (Taylor’s Version)

Taylor Swift - Dear John (Taylor's Version) (Lyric Video)

Dear John isn’t just a sad song about how hurt Swift is, it’s a track where she delivers one of the most scathing indictments of a former lover you’ve ever heard come from her. The relationship ended, but the end of it did nothing but make her realize how badly she had been treated.

Writing and recording the song was likely a cathartic performance for her, allowing her to get all of her sadness and anger out without—openly—naming who it was directed at… eyes on you John Mayer. It’s a masterpiece among her many great works, perfectly capturing the emotion of the heartbreak she was experiencing while still showing her strength and resilience. 

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5. Maroon

Taylor Swift - Maroon (Official Lyric Video)

Maroon is a song that has been debated quite a bit by Swift fans. As a darker shade of red, maroon seems to be a darkening of the themes from her Red album. Over time and distance, love has seemingly faded away, at least to an extent. That weakening of the armor was something that fans could easily relate to, and it was likely partly related to her single Death By A Thousand Cuts.

Fans have speculated about who the song was written about, even going as far back as 2009 to ID the perpetrator. In the end, it hasn’t ever been revealed, adding another layer of sadness to the light fading from her loving fire. 

6. Last Kiss (Taylor’s Version)

Taylor Swift - Last Kiss (Taylor's Version) (Lyric Video)

Last Kiss may be the Swift song that best sums up the tidal wave of emotions that come in the aftermath of a breakup. Regret, shock, sadness, hopelessness, frustration, and even the overwhelming feeling of wanting to make things right are all viable things to talk about, and she does them all. Even the melody of this track is a sad one, perfectly backing her lyrics that describe the utter pain of losing someone you’ve invested so much time, energy, and emotion into. 

7. Cold As You

Unrequited love is another popular theme in Swift’s music, especially in her earlier albums. Cold As You describes how much she wants to be with someone. Unfortunately, that someone appears to not want the same thing and actively works against it. For her, it’s utter agony, captured perfectly in the lines of this song.

She aches at wanting to be with the person but knows that they either can’t or won’t return her feelings the way she wants them to. It serves as a release valve for both she and people who have dealt with those feelings, giving them an outlet for such strong emotions.  

8. The Archer

Taylor Swift - The Archer (Lyric Video)

Not every sad song has to be about a relationship, even if it’s coming from Swift. The Archer takes on the terrible feelings of self-doubt and insecurity, two things you might not expect to be part of such a successful star’s life. Her fears of not living up to people’s expectations, being judged, and struggling with those doubts are told in a heart-wrenching way.

It also gives a bit of an explanation for why some of those relationships turned sour, as when she’s going through them she tends to push people away. It’s sad because it’s a reminder that she is a human who deals with many of the same paralyzing emotions that her fans do. 

9. Forever & Always (Piano Version) (Taylor’s Version)

Taylor Swift - Forever & Always (Piano Version) (Taylor's Version) (Lyric Video)

Swift writes breakup songs like no other, digging into the raw emotions that come along with the end of what should have been a satisfying and happy relationship. Her track Forever & Always deals with her public breakup with Joe Jonas and how painful it was for her to go through.

The song mainly talks about all of the promises they made to each other and how good the relationship had been, but the acknowledgment that it’s time to move on is almost an unbearable addition to the track. It’s Swift at her rawest, truest, and most vulnerable. 

10. Soon You’ll Get Better

Taylor Swift - Soon You’ll Get Better (Official Audio) ft. The Chicks

Cancer is a beast that touches every person’s life in one way or another. For Swift, it was her mother who ended up battling the heartbreaking disease. Soon You’ll Get Better was written about her mother’s fight against cancer and stood as her hope that eventually she would win the battle and get back to being healthy.

It’s full of strength, love, power, and hope. Anyone who listens will likely be moved to tears by the touching tribute while many others will be able to relate to how she was feeling when she put pen to paper and wrote this track. 

11. illicit affairs

Taylor Swift – illicit affairs (Official Lyric Video)

There are very few times that Swift doesn’t put her emotions into her songs, but this one seems to take it to another level. Lines like “Don’t call me kid, don’t call me baby. Look at this godforsaken mess that you made me. You showed me colors you know I can’t see with anyone else.”

It tells you exactly how much pain she’s going through and how belittled she feels by the man who has left her devastated. It’s undeniable how much she was going through when she wrote it and her ability to capture those moments and emotions is exactly the thing that makes people love her so much. 

12. Back To December

Taylor Swift - Back To December

Back To December is a particularly interesting breakup song in Swift’s discography, as it isn’t about the pain she felt for being left or the wrongs done to her in a relationship. It’s all about how her relationship ended and it was all her own fault. It’s a track full of regret, wishing to take responsibility for her role in the relationship failing and wanting to go back in time to have done a better job of treating them right.

It marked a shift in her songs that showcased her as more of a mature and introspective singer rather than a reactive one. The track isn’t emotionally simple, but it is an acknowledgment by her that sometimes she was the one who was wrong. 

13. White Horse (Taylor’s Version)

Taylor Swift - White Horse (Taylor's Version) (Lyric Video)

White Horse is a bit of an emotional mix when it comes to Swift’s songs. It’s obviously a sad track, dealing with the trauma she’s gone through and pondering over the memories of past relationships that still haunt her. In the end, her vocal delivery on this song is the thing that raises hairs on your arms and forces you to feel something. But it doesn’t end on the saddest note of all of her tracks, as there’s a hint of resiliency and hope that comes through, even in the middle of such a heartbreaking time. 

14. This Love

Taylor has a very hard time getting over relationships, especially when she isn’t the one to end them. Anyone who has gone through the same things can easily relate to her work, but This Love sees her meeting up with an old flame and reflecting on their relationship together.

It brings back all of her old feelings, making her feel sad as she tries to deal with navigating a new friendship with someone that she still has feelings for. It talks about her regrets in the relationship and how painful the separation is while acknowledging that it’s all over. 

15. Teardrops on My Guitar

Taylor Swift - Teardrops On My Guitar

Teardrops On My Guitar is one of Swift’s earliest hit singles but that doesn’t mean it lacks the depth of emotion she’s become so well known for. It’s a snapshot of her frame of mind as she grew into her music career and dealt with the typical problems of any teenager.

From having to learn to grow up to the pain of teenage heartbreak, her emotions are on full display. Dealing with unrequited love and seeing her hopelessly devoted to someone who doesn’t even know who she is is painful for Swift and fans alike. But despite it being such a hard road, she still believes that love is worth fighting for. 

16. Red (Taylor’s Version)

Taylor Swift - Red (Taylor's Version) (Lyric Video)

Red, both the song and album by Swift, explores the deep pains of one of her past relationships that just doesn’t seem to fade over time. It was something that has had a profound impact on her life, never really going away despite her belief for a time that she had moved on. She famously uses different colors to symbolize different aspects of a relationship. In this one, red seems to symbolize an intense passion and the sadness that comes from watching it slip through your fingers. 

17. Breathe (Taylor’s Version)

Taylor Swift - Breathe (Taylor's Version) (Lyric Video) ft. Colbie Caillat

Not every sad song has to be devoid of hope that things will get better. Swift, better than almost anyone, is able to explore the complex emotions of a breakup in a way that many other artists simply can not. Breathe is an incredible song on its own, but when Colbie Caillat got involved in Taylor’s Version of the track, it got even better.

Of course, the song is sad because it deals with heartbreak, but it does hold out the hope that eventually healing is going to happen. It’s vulnerable, relatable, and full of all the emotions we’ve come to expect from the legendary Taylor Swift. 

18. Speak Now (Taylor’s Version)

Taylor Swift - Speak Now (Taylor's Version) (Lyric Video)

Speak Now was the title track of one of Swift’s most provocative and amazing albums of all time. It was meant to embody the concept of taking the chance to say something before it was too late to do so. In this song, the narrator finds herself speaking up at a wedding as a final attempt to win back an ex-boyfriend.

While I don’t think she did this in actuality, the metaphor is a powerful one for the pain of losing a person you love and the desire to want them back. It’s a sorrowful performance from her and one of her best early entries to her saddest tracks repertoire. 

19. You Belong With Me

Taylor Swift - You Belong With Me

You Belong With Me is one of Swift’s earliest and most famous songs of unrequited love. She paints the picture of her being the invisible girl who is desperately in love with a guy who barely knows about her existence. She continually pines over the boy, but at the time, he’s in a relationship with someone else.

As the track progresses, she becomes more frustrated and animated, not only because of her own feelings but also because he’s being mistreated by the other girl. She believes she knows him better and would be a much better option for him. In spite of this, it never comes to be and she imagines a world in which the two are able to end up together. 

20. Long Live (Taylor’s Version)

Taylor Swift - Long Live (Taylor's Version) (Lyric Video)

Long Live might not have been meant to be a sad song. It’s a tribute to her friends, fans, and all the other people who have made her music career possible. In many ways, it’s a touching track that sees Swift showing appreciation for all the positive people in her life.

The sad part of the song comes in with the reminder to always remember the good times with people around you. It can make you remember a person you’ve lost or have regrets over not appreciating the right people, adding a layer of sadness to a track that otherwise could have been entirely positive. 

21. exile

Taylor Swift – exile (feat. Bon Iver) (Official Lyric Video)

The track exile is another ponderance on the feelings of love and loss, as well as the way they can affect the way we view things in life. It’s one of her best piano melodies, and Bon Iver’s vocals add an extra haunting component to the song that is sure to tug on your heartstrings.

The track tells the story of two lovers who are both struggling to move on from their ended relationship. Swift and Bon Iver trade verses, almost sparring with each other over the pain and confusion they’re going through after the breakup. By the end, the song has a sense of acceptance to it, with both lovers coming to terms with the fact that they are no longer together. 

22. The Last Time (Taylor’s Version)

Taylor Swift - The Last Time (Taylor's Version) (Lyric Video) ft. Gary Lightbody

The Last Time is yet another haunting entry to Swift’s discography. Alongside Gary Lightbody, this version of the song produces some of the most poignant melodies and vocal harmonies in her entire repertoire. Again, she discusses a breakup, talking about the hopelessness, desperation, and longing associated with the end of that relationship.

It’s a track that will bring up memories of a bad breakup in any listener, a kind of universally sad track that only she would be able to craft. It helps that the chemistry between the singers is amazing, creating perhaps the most emotional and saddest duet she has ever been able to put together. 

23. Sad Beautiful Tragic (Taylor’s Version)

Taylor Swift - Sad Beautiful Tragic (Taylor's Version) (Lyric Video)

Sad Beautiful Tragic is one of the best examples of the heartbreak at the end of a relationship in all of Swift’s songs. Coming from her Red album, the track is one of her deepest lyrical ventures and mixes in the perfect level of melancholy feelings.

Perhaps no other song is a better reminder of how easy it is for her to tap into an audience’s emotions, even without a direct subject or story behind the track that fans have figured out over the years. The end can be sad, tragic, or even beautiful in a sad kind of way. Maybe the beautiful part is that you’re no longer in a crappy situation. 

24. I Almost Do (Taylor’s Version)

Taylor Swift - I Almost Do (Taylor's Version) (Lyric Video)

Most people who have gone through a tough breakup have had the urge to try reaching out to their ex. Some might have even sent those “I miss you” texts. It’s almost never a good idea, especially when they were the ones who ended things.

Swift takes on all those emotions, from nervousness to regret and grief to hopelessness in her song I Almost Do. It’s not her only track that deals with wanting to go speak to one of her exes and try to work things out, but it is one of the saddest songs in her repertoire. 

25. tolerate it

Taylor Swift - tolerate it (Official Lyric Video)

The track tolerate it is all about a relationship that feels mired in indifference. Regardless of behavior, it’s tolerated by both sides because they seem to just not care enough. The song is sad because she wasn’t the indifferent one in the situation. She was the one trying. But all of her efforts were met with a remarkable lack of appreciation.

The lyrical abilities of Swift are on display in this one, serving as one of her most creative and strong songwriting performances. The neglect is another thing fans can likely latch onto and relate to. 

26. august 

Taylor Swift – august (Official Lyric Video)

Summer flings are a common theme for a lot of songs, and while some may portray them in a joyous way, the one truth about summer love is that it almost always ends when the season does. Swift’s single august beautifully portrays all of those feelings, from losing someone you were never really with to accepting that the relationship is on a timer that’s winding down.

It’s sad because of how bittersweet all of the feelings in the track are. While things didn’t go poorly, or even end poorly in all honesty, it’s going to fade away regardless of how she feels or what she wants to happen. 

27. Come Back…Be Here (Taylor’s Version)

Taylor Swift - Come Back...Be Here (Taylor's Version) (Lyric Video)

Distance is one of the biggest hurdles a relationship can overcome, with many not actually being able to do it. No matter how much you love someone, being far away from them hurts in a way that’s hard to describe. It becomes even more of a problem if you’re famous or traveling all the time.

Swift takes that on in her single Come Back…Be Here, a song that’s all about the desire to be with your long-distance partner. It eloquently tries to describe the pain of being away from the person you love and the desire to be next to them. It might not be the saddest track for everyone, but anyone trying long-distance might have their eyes watering by the end of it. 

28. Better Man (Taylor’s Version)

Taylor Swift - Better Man (Taylor's Version) (From The Vault) (Lyric Video)

Swift is at her best when she pulls out her stripped-down acoustic stylings. Better Man, the version from her vault, is a haunting ballad that she threw all of her vulnerabilities and anguish into. She describes wanting a lover who isn’t particularly a good person, wishing they were a better man and that things could have worked out differently.

The pain and longing in her voice are palpable, and the song stands as a poignant one for anyone who has developed feelings for the wrong person at the wrong time. 

29. champagne problems

Taylor Swift - champagne problems (Official Lyric Video)

If you ever need a good example of what an amazing storyteller Swift is, look no further than champagne problems. The song has a haunting melody that does nothing but perfectly back the emotion of her lyrics and vocal prowess in the track. It sees her taking on the role of a woman who has turned down a proposal from her partner.

In spite of the proposal being romantic—and expensive—she felt as though she couldn’t say yes and ended up dealing with the aftermath. There are always plenty of complicated emotions involved in a situation like this, but in between the sadness and anger, you’ll find a few hints of relief. 

30. You’re Not Sorry (Taylor’s Version)

Taylor Swift - You're Not Sorry (Taylor's Version) (Lyric Video)

What’s worse than being done wrong by someone? Frankly, when they don’t even feel sorry about the injustices they’ve done to you or even smugly wipe your nose in it. Another ballad about the aftermath of a relationship, You’re Not Sorry deals with the weight that comes with the realization that the person who has hurt you doesn’t even care.

It’s especially sad when this comes from someone you thought loved you, or if not, at least cared for you the slightest bit. The themes of betrayal and sorrow echo deeply within this haunting T-Swift song. 

31. hoax

Taylor Swift – hoax (Official Lyric Video)

Being lied to by the person you love is one of the most painful experiences you can go through in life. And it doesn’t matter what they’re actually lying about, whether that be cheating on you, their feelings for you, or even small things about their life.

The track hoax is the perfect song to capture those feelings, delivering on the feelings of betrayal that come from being lied to and laying out all of the vulnerabilities that rise to the surface when things like that happen. Among the tracks on her folklore album, it remains one of the saddest and perhaps the most emotional songs. 

32. Clean

Clean is a sad song that might make you cry, but the tears will come more due to a sense of relief than the actual sadness. Droughts killing flowers they grew together is a great metaphor for how the relationship in the song ended, though it also serves another purpose. The death of those flowers makes room for new things to grow, adding a sense of renewal and fresh possibilities to a track that would otherwise be heart-wrenching.

All in all, this is meant to represent the moment you are no longer drowning in the aftermath of a relationship, the very moment the raw emotions wash away and you can begin planning your next steps. 

33. Tied Together With A Smile

Tied Together with a Smile

Tied Together With A Smile is one of Swift’s saddest songs that doesn’t directly discuss the tragic end of a relationship. Instead, it dives into the turmoil of mental health problems and how dealing with expectations can leave a person crippled with anxiety.

She’s obviously talking about herself in the track, describing how she tries to keep up an outward appearance in spite of the internal pressure she puts on herself and her boiling emotions under the surface. It’s another song that she slides a sliver of hope into, reminding herself and her fans that they aren’t alone in their struggle and that asking for help is okay. 

34. The Moment I Knew (Taylor’s Version)

Taylor Swift - The Moment I Knew (Taylor's Version) (Lyric Video)

At some point in every failed relationship, there comes a moment when you realize it’s over and there’s no going back. There’s a finality to that moment, and it’s the start of a long process that involves processing the emotions involved, grappling with guilt, and trying to move on.

It’s draining, emotionally, mentally, and physically. The Moment I Knew is that song for Swift, describing the exact moment she knew that her happiness—at the time—was at an end and when she realized she had to figure out what came next. 

35. Never Grow Up (Taylor’s Version)

Taylor Swift - Never Grow Up (Taylor's Version) (Lyric Video)

Time is the one thing that will always move on, no matter how hard you try to stop it. You’re going to get older, things are going to change, and water is wet. This we all know. However, the loss of childhood innocence is something that creeps up on people, and it’s hard to recognize exactly when it’s going to be gone.

Swift captures that perfectly in Never Grow Up, a song that acknowledges the inevitability of growing up and having to become an adult in spite of your own wishes. It serves as a tribute to youth but also a reminder to hold onto it as long as you possibly can. 

36. evermore

Taylor Swift - evermore (Official Lyric Video) ft. Bon Iver

The track evermore is yet another example of Swift’s ability to describe the bittersweet acceptance of a relationship ending. It’s one of her most somber songs, describing the aftermath of a relationship and comparing it to a neverending winter.

It’s the loneliness and the heartbreak she focuses on in this track that hit close to home for many of her listeners. But it also has a level of depth to it that, while not unique in her music, still helps this one stand out as one of the most sad songs in all of her repertoire. 

37. Death By A Thousand Cuts

Taylor Swift - Death By A Thousand Cuts (Official Audio)

Death By A Thousand Cuts might be an awesome song title for a metal track, but Swift’s song by that name is utterly stunning. It’s more uptempo than most of her depressing ballads but that doesn’t stop it from being sad.

It describes a relationship slowly falling apart, dying slowly thanks to the many small problems that pop up rather than any big event that ends it in an instant. It contains a feeling of helplessness, that an unstoppable end is coming, but it’s taking so long that it draws out the pain. Without the dramatic end, it feels even worse to watch a relationship end. 

38. New Year’s Day

New Year’s Day is the closing track for Swift’s Reputation album and describes exactly what is advertised. It’s about the aftermath of a New Year’s party, illustrating how her house is left in tatters as everyone is heading out the door.

While it seems to be a message of gratitude and love to the people who were there and helped clean up afterward, it also showcases the loneliness of being in a home by yourself. It’s not the saddest song in her catalog, but the reminder that life is worth living and finding beauty in everyday moments makes all the difference and is just as emotional as her heartbreaking breakup ballads. 

39. coney island

Taylor Swift - coney island (Lyric Video) ft. The National

The track coney island is a song that takes on some indie rock influences from The National that are largely absent in a lot of her other works. It helps it stand out as a single, adding a new layer to the onion that is Swift. The song itself ponders the lingering memories of a former relationship, elevated by the incredible collaboration. 

40. Bigger Than The Whole Sky

Taylor Swift - Bigger Than The Whole Sky (Lyric Video)

Sometimes, we don’t even need to know the story behind a song for it to bring up powerful emotional reactions. Bigger Than The Whole Sky is perhaps the best example of that in Swift’s catalog of songs, as it simply deals with the loss of a loved one.

By painting the picture that they were bigger than the sky, she shows just how important the person was to her and the size of the gap left after their departure. It was an incredibly emotional track from her Midnights album that anyone who’s dealing with the loss of a loved one is going to be able to relate to. 

41. Love Story

Taylor Swift - Love Story

Look, Love Story is not a song you would have expected to end up on this list. It feels like a fantasy story about the perfect kind of love and it describes an incredibly cute relationship. So, how did this warm and fuzzy track end up on this list?

Most of Swift’s songs are written about a specific person, even if she does remain tight-lipped about the identity of the person the song is about. Love Story, for how amazing the track sounds and how happy it is, isn’t about one of her relationships. It’s a literal daydream that is made sad in retrospect, as the painful breakups she’s gone through and her still—at least at the time of writing—not being happy with someone contrasting the fantasy world hard enough to make it a sad song.

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