[Masterpiece] Tear-jerking Western songs. The tears won’t stop… truly sad songs [2026]
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.
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[Masterpiece] Tear-jerking Western songs. The tears won’t stop… truly sad songs [2026] (71–80)
DESPERADOThe Eagles
A song that depicts the stress of being a rock star, set against the backdrop of a cowboy who refuses to fall in love.
It was started in the late 1960s by Don Henley and is also included on the Eagles’ album Greatest Hits 1971–1975.
I’m With YouAvril Lavigne
If you like girls’ rock, Avril Lavigne is hugely popular and well-known in Japan.
She’s known for her energetic style, but this sorrowful ballad is highly recommended.
You can also see a new side of her, so be sure to give it a listen.
HallelujahRufus Wainwright
Among artists, only a very small number truly have real talent.
For example, someone who is Japanese and only understands Japanese might only listen to Japanese music.
A true artist is someone who can win over even a person like that.
This person is without a doubt the real deal among the real.
[Masterpiece] Tear-jerking Western songs. The tears won’t stop… truly sad songs [2026] (81–90)
Across The UniverseFIONA APPLE
There are countless artists and bands who cover songs by the Beatles, the greatest band in the world.
However, most of them fall far short of the originals, and you’d be much better off just listening to the source material.
Fiona Apple’s cover version, however, is truly outstanding.
Fingers CrossedLauren Spencer Smith
A gem of a ballad that paints the pain of heartbreak, with a sweet, aching voice that seeps into your heart.
Lauren Spencer Smith’s soaring vocals beautifully capture the complex emotions after a breakup.
Released in January 2022, the song quickly went viral on TikTok and hit number one on the charts in Ireland and Norway.
The phrase “crossing my fingers” is especially striking, deftly portraying the futility of love’s promises.
In those moments when memories of past love make your chest tighten, listening to this song might just make your heart feel a little lighter.
Small BumpEd Sheeran
About fifty years after the Kinks’ debut, an artist who exudes quintessential Britishness finally emerged and became a worldwide sensation: Ed Sheeran.
This is what’s wonderful about music—it connects across eras.
While the song carries a sense of sorrow, it is above all a magnificent piece.
Goodbye Never Felt So BadJames Bay
Let me introduce “Goodbye Never Felt So Bad,” a song that delves deeply into the sorrow of heartbreak.
It’s a rock track by British singer-songwriter James Bay.
Set to a driving, fast-paced sound, it gives voice to a woman’s sadness after being dumped by her lover.
The way it conveys grief through various metaphors is especially striking.
While the theme is bittersweet, the powerful vocals and sound might actually lift your spirits.
