Beautiful tear-jerking songs / songs that make you cry your eyes out

[Masterpiece] Tear-jerking Western songs. The tears won’t stop… truly sad songs [2026]

music writerKOH-1
Started working as a music writer as a side job while employed at a record shop, and for over 18 years I’ve contributed to music magazines, disc guide books, mooks, and web media. As a writer my main field is Western music, but as a listener for over 35 years, I always try to keep my curiosity alive with the motto “I like what I like.” I have experience playing in bands, where I was a bassist who handled songwriting and composition. Instruments I’ve played include bass, guitar, and piano. I began studying English in my mid-40s and continue to do so today.

Music has a mysterious power to heal the heart and, at times, move us to tears.

In this article, we introduce timeless Western songs that transcend language barriers and resonate deeply with the soul—sad and heartrending masterpieces.

The bittersweetness of love, the sorrows of life, the pain of parting…

We present a selection of exquisite melodies and lyrics that have touched hearts around the world, across genres and eras.

If you’re carrying something heavy in your heart right now, these songs will surely stay close to your feelings.

Please enjoy these treasured classics in the playlist here.

[Masterpieces] Western songs that make you cry. The tears won’t stop… truly sad songs [2026] (131–140)

Little Lou, Ugly Jack, Prophet JohnBelle & Sebastian／Norah Jones

Little Lou, Ugly Jack, Prophet John

Little Lou, Ugly Jack, Prophet JohnBelle & Sebastian／Norah Jones

Early Belle & Sebastian are great, but I also love them after the band matured, like in this song.

Even though it’s a sad song, I somehow want to listen to it over and over, and in the end it lifts me up.

I think that’s because there’s an appeal that draws you in—from both the band and the song.

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sad dayFKA Twigs

FKA twigs – sad day (audio)

sad dayFKA Twigs

This is a track from the second album, MAGDALENE, released in 2019 by the uniquely individual British singer-songwriter FKA twigs, five years after her debut.

As the title suggests, it’s a song that evokes sadness, said to express the feeling of growing apart from a lover.

Throughout the album, she sings about various hardships and losses she experienced after her debut, and it captures her real self, who in fact also went through a breakup with her fiancé.

Why not immerse yourself in FKA twigs’ distinctive world while reflecting on your own experiences?

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In conclusion

Timeless, melancholic masterpieces of Western music that continue to be loved across eras and borders.

Their lyrics and melodies touch the heartstrings, accompany our lives, sometimes offering comfort and at other times bringing new insights.

I hope these gems—songs that express universal emotions—serve as a chance for you to discover a piece that resonates with your heart.