The “Sad!” emoji has nothing on Taylor Swift – the singer-songwriter extraordinaire who has penned some of the most poignant and evocative songs about breakups, heartache, and longing that have become anthems for lovers of all ages.
We all know and love Swift’s more cheerful hits like “You Belong With Me” and “Shake It Off,” but there is something special about the melancholic ballads that make fans feel connected to the emotions in the lyrics.
Here, we break down the saddest Taylor Swift songs for those moments when we need a good cry. From country twang to pop melodies, these songs prove that Swift really knows how to do heartache justice.
Get ready to have all the feels – you may never be ready for it, but you won’t be able to resist.
Ronan (Taylor’s Version)
“Ronan (Taylor’s Version)” is a poignant tribute that showcases Swift’s ability to capture raw emotions through her music. The song tells the heart-wrenching story of Ronan, a young boy who lost his life to cancer at the age of four. Swift’s lyrics are poetic and vivid, painting a vivid picture of the devastation felt by Ronan’s loved ones in the aftermath of his passing.
The instrumentation is simple yet effective, matching the mournful tone of the lyrics. Swift’s voice is gentle and emotive, adding depth and nuance to the already heart-rending lyrics. As she sings about Ronan’s life and the unfortunate circumstances that led to his death, there is a poignant sense of longing and regret that permeates the entire track.
“Ronan (Taylor’s Version)” is a testament to Swift’s ability to craft deeply moving music that resonates with listeners on a personal level. It’s a song about loss, grief, and the power of love to transcend even the most tragic of circumstances. And while it’s undoubtedly a sad song, it’s also a beautiful tribute that celebrates the life of a young boy who left an indelible mark on the world.
Forever and Always (Piano Version) (Taylor’s Version)
Another poignant and emotionally charged track from Taylor Swift’s discography is “Forever and Always (Piano Version) (Taylor’s Version).” This updated version of the original song released in 2008 showcases Taylor’s raw vocals and heart-wrenching lyrics in a stripped-back production style that puts her pain at the forefront. The song is about Taylor’s breakup with Joe Jonas and the pain that came with it. She sings about the promises made and the way things used to be, while acknowledging that she needs to move on. This vulnerability and honesty make it one of the standout tracks in Taylor’s discography.
Soon You’ll Get Better (feat. The Chicks)
“Soon You’ll Get Better (feat. The Chicks)” was written about Taylor’s mother’s battle with cancer, and it’s a deeply personal and emotional song. Taylor’s lyrics are poignant and heartbreaking as she sings about the hope that her mother will get better, but also the fear that she won’t. This song is not only a testament to Taylor’s songwriting abilities but also an ode to the strength and love of her family. It’s a track that will leave you feeling deeply moved and grateful for the people you have in your life.
Back To December (Taylor’s Version)
Moving on to our next song, “Back To December,” Swift takes a different approach to expressing her regret and sorrow over a past relationship. On this track from her Speak Now album, Swift sings about a past love who she wishes she could apologize to for her mistakes. The gentle melody and melancholy lyrics perfectly capture the feeling of wanting to turn back the clock and make things right.
What makes “Back To December” particularly poignant is the way Swift takes responsibility for her role in the relationship’s demise. She acknowledges that she was the one who pushed her lover away, and now she wishes she could go back and treat him better. The chorus, with its repeated line of “I go back to December all the time,” is both haunting and beautiful.
In contrast to some of Swift’s other breakup songs, “Back To December” shows a more mature and introspective side of the singer. She doesn’t just wallow in her own pain; instead, she empathizes with the person she hurt and longs for a chance to make amends. It’s a bittersweet and emotionally complex song that showcases Swift’s growth as both a songwriter and a person.
Bigger Than The Whole Sky
Tapping into the grief of losing a loved one, Taylor Swift’s emotionally charged song “Bigger than the Whole Sky,” from her album “Midnights,” is a powerful testament to the pain of loss. In it, Taylor croons “Goodbye, goodbye, goodbye / You were bigger than the whole sky / You were more than just a short time” – a heartbreaking tribute to the past and the memories that linger. For anyone dealing with the sorrow of losing someone they love, this song is one of Taylor’s saddest and sure to resonate.
my tears ricochet
With “my tears ricochet,” Taylor Swift takes listeners on a journey of heartbreak and loss. From the opening chords, the song’s melancholic tone sets the stage for a story of pain and reflection. The haunting melody and Swift’s emotive vocals are a perfect match for the poignant lyrics that speak to the universal experience of love and loss.
As the song reaches its climax, the emotionally charged chorus of “my tears ricochet” is sure to leave a tear in the eye of even the most stoic listener. The track is a testament to Swift’s songwriting talent and her ability to connect with her audience on a deeply emotional level.
“Champagne Problems” showcases Swift’s storytelling prowess in full force. With its haunting melody and evocative lyrics, this track tells the tale of a failed engagement, with Swift taking on the role of a woman who has just turned down a proposal from her partner. Despite the fact that the proposal was extravagant and romantic, the woman simply couldn’t say yes, and now she’s grappling with the aftermath of her decision.
As we listen to the song, we’re drawn into the complex emotions that swirl around the couple. There’s heartbreak, of course, but there’s also a sense of relief and even empowerment. The woman in the song knows that she’s made the right choice, even if it means walking away from a seemingly perfect romance. It’s a powerful message about the importance of following your heart and staying true to yourself, no matter the cost.
Would’ve, Could’ve, Should’ve
Taylor Swift’s raw emotion shines through in her heartbreaking song “Would’ve, Could’ve, Should’ve”, a rumoured reflection of a past relationship. As we listen, we get a glimpse into the complexities of the relationship, and the pain that remains after its end.
Swift’s lyrics paint a vivid picture of her regrets, lines like “God rest my soul/ I miss who I used to be/ The tomb won’t close/ Stained glass windows in my mind/ I regret you all the time” showing us the intensity of her emotions.
As the song builds, we understand the weight of her loss as she sings: ” I can’t let this go/ I fight with you in my sleep/The wound won’t close/ I keep on waiting for a sign/ I regret you all the time.” An intensely powerful and introspective track, “Would’ve, Could’ve, Should’ve” is one of Swift’s most heart-wrenching songs yet.
Dear John (Taylor’s Version)
In “Dear John,” Swift delivers one of her most raw and emotional performances yet. The song is a scathing indictment of a former lover who did her wrong, and Swift holds nothing back as she recounts the pain and heartbreak he caused her. Her voice is both vulnerable and powerful, as she expresses her anger, disappointment, and sadness.
As we move further down our list of the saddest Taylor Swift songs, “Dear John” stands out as a true masterpiece. It’s a heartbreak anthem that captures the pain of a broken relationship with stunning clarity and honesty. And yet, even in the midst of all the hurt and anguish, there is a sense of strength and resilience in Swift’s lyrics.
Taylor Swift’s songwriting talent is summed up perfectly in her track “tolerate it,” an emotionally charged portrait of a relationship rooted in indifference and neglect. Through heart-rending lyrics like “If it’s all in my head tell me now/Tell me I’ve got it wrong somehow/I know my love should be celebrated/ But you tolerate it,” Swift proves yet again her remarkable lyrical genius and confirms her place as the queen of lyricism. “tolerate it” deserves to be admired and celebrated.
Better Man (Taylor’s Version) [From The Vault]
“Better Man (Taylor’s Version) [From The Vault]” showcases Taylor’s raw and emotional songwriting style. The stripped-down acoustic sound and vulnerability in her voice make for a hauntingly beautiful ballad that tugs at the heartstrings. As she sings about wanting a lover who can be a better man, we feel every ounce of pain and longing in her voice.
With her powerful lyrics and poignant delivery, Taylor reminds us once again why she is a master of storytelling through song.
Moving on to the next song on our list, “august,” we find Taylor Swift exploring the theme of summer love. The track tells the story of a summer fling that ultimately ends in heartbreak, with Taylor’s vocals conveying a sense of wistfulness and longing. As we listen to the lyrics, we can almost feel the warm breeze of a summer evening and the ache of losing someone who was never really ours to begin with.
What’s interesting about “august” is the way that Taylor captures the fleeting, ephemeral nature of summer romance. While the song is undeniably sad, there’s also a sense of acceptance and understanding in the way that Taylor sings about her experience. She knows that the summer will end and the relationship will fade, but she’s able to appreciate the beauty of the moment nonetheless.
This sense of bittersweet acceptance is a hallmark of Taylor’s songwriting, and it’s something that she explores further in “evermore (feat. Bon Iver),” the next song on our list. In this track, Taylor reflects on the idea of lost love and the way that it can shape our perceptions of the world around us. As we delve deeper into the song, we’ll see how Taylor uses her music to explore the complexities of human emotion and the power of connection.
evermore (feat. Bon Iver)
Another song that showcases Taylor’s ability to convey bittersweet acceptance is “evermore (feat. Bon Iver).” The haunting melody and Bon Iver’s addition to the track create a somber tone that draws the listener in. In “evermore,” Taylor sings about the aftermath of a relationship’s end, and the way that it can feel like a never-ending winter. The lyrics paint a picture of loneliness and heartbreak, but there’s also a sense of hopefulness in the way that Taylor sings about moving on.
As with many of Taylor’s sadder songs, “evermore” is the kind of track that can hit close to home for listeners who have experienced the pain of lost love. The song’s emotional depth is a testament to Taylor’s ability to connect with her audience through music. “evermore” is a poignant reminder that sometimes the most painful experiences in life can also be the ones that lead to the most growth.
You’re Not Sorry (Taylor’s Version)
As we delve further into Taylor’s discography, we arrive at “You’re Not Sorry (Taylor’s Version),” a powerful ballad about betrayal and the painful aftermath of a broken relationship. With haunting melodies and poignant lyrics, Taylor guides us through the tumultuous emotions of heartbreak, capturing the rawness of pain and sorrow with every note.
The track begins with a slow, mournful piano riff that sets the stage for Taylor’s piercing vocals. As she sings about the aftermath of a failed relationship, we can feel the weight of her pain and anguish.
Breathe (Taylor’s Version) (feat. Colbie Caillat)
“Breathe (Taylor’s Version) (feat. Colbie Caillat)” is a beautiful collaboration between Taylor Swift and Colbie Caillat that showcases the magic that can happen when two talented artists come together. The song explores the pain and heartbreak of a failed relationship, but also the hope and healing that can come from letting go. As we listen to Taylor and Colbie’s harmonies, we can feel the emotion and vulnerability that went into creating this masterpiece.
Sad Beautiful Tragic (Taylor’s Version)
Nothing captures heartbreak after a failed relationship quite like Taylor Swift’s classic “Sad Beautiful Tragic”. From her “Red” album, this somber ballad keeps us captivated with its lyrical depth and melancholic melody. Taylor’s raw emotion shines through, tugging our heartstrings and leaving us in awe of her songwriting prowess. There’s no denying this is one of Taylor’s saddest songs – a hauntingly beautiful reminder of her power to make us feel.
Taylor Swift’s words and emotions in “illicit affairs” express heartbreak in a masterful way. Her words paint a vivid picture of the devastation of a relationship ending: “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.” Her lyrics evoke a feeling of undeniable pain and loss — a feeling that Swift captures in her music like no other artist.
Cold As You
Moving on from the complexity of “illicit affairs,” Taylor brings us to the familiar theme of unrequited love in “Cold As You.” The haunting melody and evocative lyrics perfectly capture the agony of loving someone who can’t return those feelings. Taylor’s pain is palpable as she sings, “And you come away with a great little story / Of a mess of a dreamer with the nerve to adore you.” We can feel the ache in her voice as she describes the frustration of knowing that her love will never be enough for this person. But as with all of Taylor’s songs, there is a sense of release that comes with acknowledging these raw emotions.
Last Kiss (Taylor’s Version)
As we’ve seen throughout this list, Taylor Swift has a knack for writing heartbreaking songs that cut straight to the core of the listener’s emotions. And with “Last Kiss,” she continues to show us just how powerful her songwriting can be.
In “Last Kiss,” Swift explores a relationship that has already ended, with the two former partners saying their final goodbyes. As the song progresses, we can feel the weight of their shared history hanging heavily in the air. It’s a poignant moment that feels all too familiar for those who have experienced a similar situation.
White Horse (Taylor’s Version)
Moving on to another heart-wrenching track, we have “White Horse (Taylor’s Version).” As with many of her songs, Taylor’s ability to convey raw emotions through her lyrics shines through in this heart-rending ballad. It’s impossible not to feel moved by the haunting melody and Taylor’s powerful vocal delivery.
Despite the sadness that permeates “White Horse (Taylor’s Version),” there’s also a sense of hope and resilience that shines through. Taylor’s lyrics remind us that even in the midst of heartbreak, there’s always the possibility of finding something better.
Clean (Taylor’s Version)
As we’ve seen with the previous songs on this list, Taylor Swift has a gift for perfectly capturing the pain of heartbreak in her music. But with “Clean,” the final track on her album “1989,” she offers a glimmer of hope. The song acknowledges the end of a relationship with lyrics like “The drought was the very worst / When the flowers that we’d grown together died of thirst,” but also contains a sense of renewal and moving on.
After the raw emotions of the previous songs, “Clean” feels like a breath of fresh air. The lyrics describe the process of healing and moving forward, with lines like “Rain came pouring down / When I was drowning, that’s when I could finally breathe.” Swift’s voice sounds lighter and more optimistic, signaling a turning point in the album and in the protagonist’s journey.
“Clean” is a reminder that even when things feel hopeless and devastating, there is always a chance for renewal and growth. It’s the perfect note to end the album on, and a strong representation of Swift’s ability to capture the complex emotions of heartbreak in her music.
“Hoax” is a heart-wrenching song that delves into the aftermath of a failed relationship. Swift’s vocals are haunting and vulnerable, capturing the sense of betrayal and hurt that comes with being lied to by someone you loved. The stripped-down instrumentation adds to the song’s melancholic atmosphere, making it one of the most emotional tracks on the album.
Tied Together With A Smile
“Tied Together With A Smile” offers a poignant perspective on the challenges of mental health and the weight of societal expectations. In this heart-wrenching ballad, Taylor Swift explores the inner turmoil of a young woman who outwardly appears to have it all together, but is struggling silently with the internal pressure to keep up appearances.
As she sings, “You’re tied together with a smile, but you’re coming undone,” Swift highlights the harsh reality that many people face when dealing with mental illness: the need to put on a brave face and pretend that everything is okay, even when it’s not.
Despite the heavy subject matter, there is a glimmer of hope underlying the song’s melancholy melody. Swift reminds us that we are not alone in our struggles and that it’s okay to ask for help when we need it. By shining a light on the importance of mental health awareness, “Tied Together With A Smile” is both a heartbreaking and empowering anthem for anyone who may be going through a difficult time.
The Moment I Knew (Taylor’s Version)
“The Moment I Knew” is Taylor Swift’s poignant reflection on the exact moment she realized her relationship was over. It’s a relatable song that deals with the universal experience of heartbreak and the draining process of moving on. In the first verse, she sings about getting ready for a party, all dressed up and full of hope that her boyfriend will come there and fix everything. But as the night goes on and he doesn’t show up, she realizes the truth and that puts her in a vulnerable position.
Swift’s delivery of the lyrics is heart-wrenching, and “The Moment I Knew” stands out as one of the sadder songs in her discography. It’s a moving testimony to the fact that heartbreak can be just as devastating as any other form of loss. The song is a reminder that life can be unpredictable, and one moment can change everything. Ultimately, Swift’s ability to craft honest and emotional songs has endeared her to listeners worldwide, and “The Moment I Knew” is a perfect example of that.
The Last Time (Taylor’s Version) [feat. Gary Lightbody]
Another song that is sure to tug at your heartstrings is “The Last Time.” The haunting piano melody interweaves with Taylor and Gary’s vocals seamlessly, creating a sense of desperation and longing. It’s a hopeless and honest portrayal of the aftermath of a breakup, with both Taylor and Gary pouring their hearts out in every line. As we listen to this melancholic masterpiece, we can’t help but think of our own experiences with failed relationships.
What’s striking about “The Last Time” is how well Taylor and Gary’s voices complement each other. The chemistry between them is undeniable, making this song one of the most emotional duets in Taylor’s discography. Their voices soar and intertwine, blending together to create a sense of raw vulnerability.
this is me trying
As we move on to the next track, “this is me trying,” we can feel Taylor’s resolve to keep pushing forward even when things get tough. Despite the setbacks and heartache, she refuses to give up on love or on herself. She knows that love requires effort and a willingness to try again, even when things seem impossible.
Never Grow Up (Taylor’s Version)
“Never Grow Up” is a poignant reminder that time waits for no one. The song captures the magic of childhood with its vivid imagery and nostalgic lyrics, but also acknowledges the inevitable reality of growing up and facing life’s challenges. Swift’s vocals are raw and vulnerable, giving the track a raw emotional power that is difficult to ignore. It’s a fitting tribute to the innocence and wonder of youth, and a somber reflection on the fleeting nature of time.
exile (feat. Bon Iver)
As we move on to the next track on our list, “exile (feat. Bon Iver),” we see Swift continuing to explore the complexities of love and loss. The haunting piano melody and Bon Iver’s haunting voice perfectly complement Swift’s melancholic lyrics, making it one of the standout tracks on her album “folklore.”
“Exile” tells the story of two former lovers who are struggling to move on from their relationship. Each verse is filled with raw emotion, with Swift and Bon Iver trading verses that convey the pain and confusion that often comes with a breakup. Despite the sadness that permeates the song, there is also a sense of acceptance – both parties have come to terms with the fact that their love has ended.
I Almost Do (Taylor’s Version)
“I Almost Do” paints a vivid picture of post-relationship agony and despair. Taylor Swift’s lyrics capture the excruciating struggle one faces when the desire to contact an ex is present, but the fear of another goodbye prevents them from doing so: “I bet it never ever occurred to you, that I can’t say hello to you and risk another goodbye.” Heart-wrenching and incredibly powerful, this song from her iconic “Red” album is one of her best.
Death By A Thousand Cuts
Despite the upbeat tempo of “Death By A Thousand Cuts,” the lyrics tell a story of heartbreak and a relationship slowly falling apart. The painful realization of growing apart is palpable in Taylor’s voice as she sings about the small paper cuts that eventually lead to the end of a love affair.
It’s a relatable theme that many listeners can resonate with, as relationships often end not with a bang but with a series of small disappointments. The haunting melody and emotional lyrics make “Death By A Thousand Cuts” one of Taylor’s most poignant songs.
And yet, as we move on to our next entry, “coney island (feat. The National),” we can sense a shift in tone. The collaboration between Taylor and The National brings a new depth to her storytelling, as she explores the memories and regrets of a former romance.
coney island (feat. The National)
As we continue our exploration of Taylor Swift’s discography, “coney island (feat. The National)” is another standout track. The haunting melody and emotive lyrics take listeners on a journey through the past, as Taylor reflects on a former relationship and the memories that still linger.
With The National’s indie-rock influence, the song takes on a new depth and richness, as the haunting harmonies and brooding instrumentation add to the sense of nostalgia and sadness. It’s a masterful example of how collaboration can elevate an already great song to new heights.
“The Archer” is an introspective ballad that delves deep into the complexities of self-reflection. With its dreamy synths and subtle percussions, the song perfectly sets the mood for Swift’s candid lyrics about her shortcomings and insecurities. The track gracefully touches upon the theme of self-discovery and emphasizes the importance of acknowledging one’s flaws to overcome them.
All Too Well (Sad Girl Autumn Version) [Recorded at Long Pond Studios]
“All Too Well” is a hauntingly beautiful song that has resonated with fans since its initial release in 2012 and ever more so since its re-release in 2021. The 10 minute version of Taylor Swift’s popular track “All Too Well” took the world by storm and is a favorite amongst Swifties.
The tumultuous relationship in Taylor Swift’s lyrics is an emotionally-charged rollercoaster ride of heartbreak and longing. Yet, amidst the pain and sadness, there is a sense of hope and strength that permeates the track.
Teardrops On My Guitar
As fans, it’s no secret that we look to Taylor Swift’s music to help us navigate through some of our most difficult emotions. From the pain of heartbreak to the struggle of growing up, Swift’s music has an uncanny ability to connect with us on a personal level. One song that has stood the test of time as a favorite among fans is “Teardrops On My Guitar.” While it may not be as heart-wrenching as some of Swift’s other ballads, it still manages to capture the essence of unrequited love in a truly raw and emotional way.
As the song begins, we are transported back to the feeling of unrequited love and all the pain that comes with it. Swift’s voice is soft, yet charged with emotion as she sings about a love that will never be returned. The lyrics paint a picture of a girl who is hopelessly in love with someone who barely acknowledges her existence. It’s a feeling that so many of us can relate to, and Swift captures it perfectly.
Despite the heartache that “Teardrops On My Guitar” embodies, there is a glimmer of hope in the song as well. By the end of the track, Swift reminds us that even though love can be painful, it’s still worth fighting for.
New Year’s Day
“New Year’s Day” is a stunning showcase of Taylor Swift’s songwriting abilities. The track, which closes out her sixth studio album “Reputation,” is a poignant ballad about the aftermath of a wild New Year’s Eve party. The simple, yet evocative lyrics paint a picture of a house left in disarray, with glitter on the floor and bleary-eyed guests stumbling out the door.
At its core, “New Year’s Day” is a song about the simple comforts of home and the people who make it feel like one. Swift delivers a heartfelt ode to the person who stays behind to clean up the mess and the one who wakes up early to make coffee. It’s a message of love and gratitude for the people who stick by us when the party’s over and the confetti has settled.
“New Year’s Day” is a departure from Swift’s earlier breakup anthems, but it’s no less emotionally layered. In fact, it showcases the singer’s growth as a songwriter and her ability to find beauty in the everyday moments that make life worth living. The track is a reminder that even in the midst of chaos and heartbreak, there is always hope for brighter days.
In The End
From heartbreak to self-reflection, Taylor Swift is a master at infusing her songs with depth and complexity and has always had a way of inspiring us to examine our own lives and emotions. This list of the best sad Taylor Swift songs is the perfect way to deep dive into her discography and examine the way she has used her music to express her own struggles and sadness. From her timeless classics to her more recent hits, each song is a window into her own inner emotions.