Taylor Swift is known to be the biggest pop star of our time. From hits like “Shake It Off” and “Anti-Hero” to underground songs like “Hoax” and “Now That We Don’t Talk”, it is undeniable Swift’s lyricism and craft is above any other artist now and before her. Although she has many fun, upbeat songs, one thing that Swift continues to do is stun and shatter with her heartbreaking storytelling. This list will be breaking down Taylor Swift’s top 20 most devastating songs (and the saddest lyric from those songs).
20. “Dear John” (Speak Now (Taylor’s Version), 2023)
Saddest Lyric: Dear John, I see it all now, it was wrong. Don’t you think nineteen’s too young to be played by your dark twisted games?
In 2010, Swift released the original “Speak Now” album, which included the track 5 song “Dear John”. This song was written by Swift about her previous relationship with John Mayer and all of the pain that came with that. She rereleased the album in 2023, keeping this track as her track 5, which is notoriously her saddest track number.
19. “Champagne Problems” (Evermore, 2020)
Saddest Lyric: You had a speech, you’re speechless. Love slipped beyond your reaches, and I couldn’t give a reason, champagne problems.
Swift wrote “Evermore” as a sister album to “Folklore” during the pandemic. “Champagne Problems” was written about a girl who thought she had found the love of her life, but then, when it mattered the most, she left him hanging.
18. “Never Grow Up” (Speak Now (Taylor’s Version), 2023)
Saddest Lyric: I just realized everything I have is someday gonna be gone.
This song was written about Swift growing up and moving out from her parent’s house. It continues to be a graduation and nostalgia song for many.
17. “Hoax” (Folklore, 2020)
Saddest Lyric: You knew it still hurts underneath my scars from when they pulled me apart.
“Folklore” was the first of the two sister albums to be released by Swift during the pandemic. She spoke about how she focused on telling made up, imaginary stories for this album. “Hoax” was written about a girl she made up in her head and her struggle with an abusive relationship.
16. “So Long, London” (The Tortured Poets Department, 2024)
Saddest Lyric: And I’m just getting color back into my face. I’m just mad as hell ’cause I loved this place.
“The Tortured Poets Department” is Swift’s latest album. The album was split into two different albums, the normal and “The Anthology”. “So Long, London” is another track 5 on this list, and it was written about her leaving London and her most recent ex-boyfriend, Joe Alwyn.
15. “Illicit Affairs” (Folklore, 2020)
Saddest Lyric: And you wanna scream don’t call me “kid”, don’t call me “baby”. Look at this godforsaken mess that you made me.
This is another beautifully written song by Taylor Swift. This was not written about herself, rather a made up character in her mind. That is the beauty of “Folklore”. She wanted it to be an escape from what was happening in the world of 2020.
14. “The Black Dog” (The Tortured Poets Department, 2024)
Saddest Lyric: How you don’t miss me in the shower and remember how my rain-soaked body was shaking. Do you hate me?
This was another song that Swift wrote about her ex, Joe Alwyn. “The Black Dog” is the name of a pub she and Alwyn used to go to in London. This song enraptures the feeling that he might one day take someone else there.
13. “loml” (The Tortured Poets Department, 2024)
Saddest Lyric: And I’ll still see it until I die, you’re the loss of my life.
This is perhaps the most heartbreaking song about Joe Alwyn is “loml”. It can be interpreted as “love of my life” or “loss of my life”. Throughout the song, she switches between the two, making it seem like she is trying to decide which she wants to define him by.
12. “Exile” (Folklore, 2020)
Saddest Lyric: You’re not my homeland anymore, so what am I defending now? You were my town, now I’m in exile seeing you out.
Swift’s storytelling shines through incredibly in “Exile”. She wrote and recorded this song with Bon Iver, who added a masculine, rich touch to the song. The back and forth of lyrics in the bridge add to the tension being built up within the music. It is supposed to represent a fight between two people who are barely holding on to their relationship.
11. “How Did It End?” (The Tortured Poets Department, 2024)
Saddest Lyric: My beloved ghost and me sitting in a tree, D-Y-I-N-G.
“How Did It End” was written about society after an established couple decides to split up. She uses words like “gasp” and “shock” to capture how people react to the no-longer-couples news. It can be a painful process, and Swift does an excellent job capturing that in the lyrics.
10. “The Prophecy” (The Tortured Poets Department, 2024)
Saddest Lyric: Spending my last coin so someone will tell me it’ll be ok.
This song is a hidden gem on “The Anthology” side of “The Tortured Poets Department”. Swift wrote this song about her struggle to find real, genuine love. She confesses that it seems that it’s been written in the stars that she will end up only ever going through the dating cycle, and not finding her forever person.
9. “All Too Well (10 Minute Version)” (Red (Taylor’s Version), 2021)
Saddest Lyric: You kept me like a secret, but I kept you like an oath. Sacred prayer and we’d swear to remember it all too well.
“All Too Well” was originally written as a 10 minute song, but for the original “Red” album in 2012, she cut it down to 5 minutes. Then, in 2021 when she released “Red (Taylor’s Version”, she released with it the original 10 minutes of the beloved “All Too Well”. The song was written about her breakup with Jake Gyllenhall and her heartbreaking healing process through it.
8. “My Tears Ricochet” (Folklore, 2020)
Saddest Lyric: You had to kill me, but it killed you just the same. Cursing my name, wishing I stayed, you turned into your worst fears.
Folklore has been deemed by fans as her most devastating album, therefor it continues to make this list again and again. Swift wrote “My Tears Ricochet” about Scooter Braun, the man who stole the masters to her first 5 albums. She had had a rocky past with Braun before this incident, however, this act of betrayal sent Swift over the edge, eventually taking back her power and rerecording her first 5 albums.
7. “Mirrorball” (Folklore, 2020)
Saddest Lyric: I’m still a believer, but I don’t know why. I’ve never been a natural, all I do is try, try, try.
As one of the first surprise songs Taylor played on the Eras Tour, it holds a special place in the hearts of many Swifties. This song, also on “Folklore”, was written about Swift’s yearn to play live shows again. She missed the love that the crowd gave her, and maybe even more-so, the love that she gave them.
6. “This is Me Trying” (Folklore, 2020)
Saddest Lyric: They told me all of my cages were mental, so I got wasted like all my potential. And my words shoot to kill when I’m mad, I have a lot of regrets about that.
Yet another Folklore song has graced this list! As the fans agree that this is the saddest song on “Folklore”, it felt only right to add it to this list. “This is Me Trying” is a beautiful piece of music that allows Swift to be vulnerable about her feelings. She describes how she’s just trying her best and no one seems to be appreciating it. We appreciate it, Taylor!
5. “Tolerate It” (Evermore, 2020)
Saddest Lyric: I made you my temple, my mural, my sky. Now I’m begging for footnotes in the story of your life.
Many fans mourned the loss of this song on the Eras Tour setlist as the “Evermore” and “Folklore” eras combined into one. This is a beloved song by many. It tells the story of a wife who feels unnoticed by her husband. She feels her husband is just “tolerating” the love that she gives him and not embracing it. It breaks many hearts and tells a beautiful story.
4. “Nothing New” (Red (Taylor’s Version), 2021)
Saddest Lyric: She’ll know the way and then she’ll say she got the map from me. I’ll say I’m happy for her then I’ll cry myself to sleep.
Swift wrote “Nothing New” about the double standards females face in today’s society and specifically in the music industry. She chose to collaborate with Phoebe Bridgers to add another female voice to this incredible story. In the song, Swift uncovers her deepest fears about being forgotten by all her friends and ending up unsuccessful. This song was added to the “Red” album as a vault track for the rerelease in 2021.
3. “The Smallest Man Who Ever Lived” (The Tortured Poets Department, 2024)
Saddest Lyric: And you’ll confess why you did it, and I’ll say, “good riddance!” ‘Cause it wasn’t sexy once it wasn’t forbidden.
With its deep lyrics and intense bridge, it’s no surprise that this track is many Swifties’ favorite off of “The Tortured Poets Department”. This song was written about her relationship with actor Matty Healy. She calls him “the smallest man who ever lived” and called him out for how poorly he treated her in the short time they were together. It has also become a fan-favorite to scream at her concerts.
2. “Bigger Than the Whole Sky” (Midnights, 2023)
Saddest Lyric: Did some force take you because I didn’t pray? Every single thing to come has turned into ashes. ‘Cause it’s all over, it’s not meant to be, so I’ll say words I don’t believe.
“Midnights” was a generally upbeat and happy album, so when the “3 Am” tracks came onto the scene, “Bigger Than the Whole Sky” shocked a lot of fans. This song was written by Swift about losing a loved one. She questions why and how in a beautiful package of lyricism and simple piano backing.
1. “Happiness” (Evermore, 2020)
Saddest Lyric: Past the blood and bruise, past the curses and cries. Beyond the terror in the nightfall, haunted by the look in my eyes that would’ve loved you for a lifetime. Leave it all behind, and there is happiness.
Many fans have stated that this is the saddest Taylor Swift song of all time. Although that is a little ironic, considering the title of the song, it could not be closer to the truth. This song captures the feelings of the last stage of grief, acceptance. She also pays homage to F. Scott Fitzgerald’s “The Great Gatsby” with lines such as “I hope she’ll be a beautiful fool…”. Swift truly knocked it out of the park with this track off of “Evermore”.