Taylor Swift's Tearjerkers: Best Cry-Worthy and Popular Songs Ranking [2026]

Long LiveTaylor Swift8rank/position

Long Live

Taylor Swift is a globally popular singer-songwriter.

While she now releases a wide range of tracks, including dance music and pop, she originally started out as a country musician.

“Long Live” is a song that lets you appreciate that side of her.

Although the lyrics are somewhat abstract, its theme of taking on new challenges struck a chord with listeners, and it has become known as a classic graduation song.

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Ryo

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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.

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Hirakawa Masako (Bōkarisuto: Sakata Mizumako)

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22Taylor Swift10rank/position

Taylor Swift – 22

A track included on the 2012 album Red is a bright pop anthem that celebrates the innocence and freedom of the early twenties.

Created by Taylor Swift in collaboration with world-renowned producers Max Martin and Shellback, the song portrays a wounded heart finding healing through time spent with friends.

Its breezy sound, blending elements of disco and 1990s rock, emphasizes anticipation for the new days ahead rather than the sadness of a breakup, and will gently support anyone facing the milestone of graduation.

It’s a song I recommend to all who want to carry the days spent with friends in their hearts and take a step toward tomorrow.

All Too Well (10 Minute Version)Taylor Swift11rank/position

All Too Well (10 Minute Version) (Taylor’s Version) (From The Vault) (Lyric Video)

Singer-songwriter Taylor Swift enjoys worldwide popularity and is known for her wide-ranging musical style, spanning country, pop, and rock.

This work is her reconstruction of a track from the 2012 classic album Red into a 10-minute-13-second extended version on the 2021 album Red (Taylor’s Version).

It became a major talking point as the longest song ever to reach No.

1 on the Billboard Hot 100 in the U.S.

Its lyrics vividly depict the pain of heartbreak, making it perfect for listening closely on long, chilly autumn nights.

She also directed the short film All Too Well: The Short Film, which lets you immerse yourself even more deeply in the world of the song through its visuals.

Cruel SummerTaylor Swift12rank/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 Swift13rank/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 Swift14rank/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.