Taylor Swift’s Tearjerkers: Best Sad Songs and Most Popular Tracks Ranked [2025]

Blank SpaceTaylor Swift8rank/position

Taylor Swift – Blank Space

This song portrays the tumult of romance with humor and irony.

Taylor Swift cleverly turns the way the media treats her on its head, exaggerating the image of a woman who dates a lot.

The lyric about writing a new lover’s name on a “blank space” symbolizes the cycle of relationships.

Released in November 2014, it spent seven consecutive weeks at number one in the U.

S.

It received high praise from critics and was nominated for a Grammy Award.

It’s a recommended track for those who’ve experienced heartbreak and want to take a closer look at themselves.

Never Grow UpTaylor Swift9rank/position

Never Grow Up

This song, released in 2010 by an American country-pop singer who is also a singer-songwriter, has heartbreakingly poignant lyrics expressing a wish for a child not to lose their pure cuteness, not to bear the burdens of the world, and not to grow up.

Moreover, those lyrics blend with her sweet, unaffected voice to evoke an indescribable feeling.

Cruel SummerTaylor Swift10rank/position

Taylor Swift – Cruel Summer (Official Audio)

A song sung by American singer-songwriter Taylor Swift that portrays the frenzy and anguish of a secret love.

It’s well known that the track became a massive hit years after its 2019 release, but despite its glittering, summery rush, the pain of a relationship that must be kept hidden is distilled into the single phrase “Cruel Summer.” The frustration of a love you can’t tell anyone about and the precarious feeling of being feverishly drawn to someone tighten listeners’ hearts.

The lyric “I love you, isn’t that the worst thing you’ve ever heard?” is heartbreakingly poignant.

Its anguished cry, carried by passionate sound, gently embraces the hearts of those struggling with the ache of a love where happiness and anxiety are entwined.

Down BadTaylor Swift11rank/position

Taylor Swift – Down Bad (Official Lyric Video)

This song, included on Taylor Swift’s album “The Tortured Poets Department,” released in April 2024, candidly portrays the pain of heartbreak.

The phrase “down bad” is repeated, strikingly expressing an obsession with a finished relationship and a profound sense of despair.

The lyrics and melody, infused with emotions born from her own experiences, create a beautiful yet melancholic atmosphere.

It features distinctive synth-pop and indie-inspired sounds, with polished production from her collaboration with Jack Antonoff and others.

If you want to face the pain of a breakup, it might be good to listen to this song and have a good cry.

lomlTaylor Swift12rank/position

Taylor Swift – loml (Official Lyric Video)

If you’re seeking an experience where a piano melody quietly resonates in your heart, you should listen to this exquisite ballad by American singer-songwriter Taylor Swift.

This work, featuring her delicate vocals and a piano-centered arrangement co-crafted with Aaron Dessner, deeply stirs listeners’ emotions with its beautiful tones.

It portrays the pain of a phrase meaning “the love of one’s life” turning into “the loss of one’s life,” and the protagonist’s profound regret upon realizing that a once-legendary relationship was fleeting and needless is truly moving.

Included on the April 2024 album The Tortured Poets Department, the song has received high acclaim, reaching No.

12 on the Billboard Hot 100.

It’s a perfect track for nights when you want to quietly shed tears and find solace in the sorrow of heartbreak.

Snow On The BeachTaylor Swift ft. Lana del Rey13rank/position

Taylor Swift – Snow On The Beach (Lyric Video) ft. Lana Del Rey

“Snow On The Beach” is an evocative ballad by singer-songwriter Taylor Swift.

The song features fellow singer-songwriter Lana Del Rey, and the way their voices blend is absolutely irresistible.

The title “Snow On The Beach” serves as a metaphor for a contradiction, poignantly expressing how the misfortune that befell her felt unbearably absurd and hard to believe.

…It’s the kind of song that might make you cry when you listen to it during really tough times.