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

Small BumpEd Sheeran

Ed Sheeran – Small Bump [Official Music Video]

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.

HallelujahRufus Wainwright

Rufus Wainwright – Hallelujah (Live At The Fillmore)

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.

BrielleSky Sailing

Sky Sailing – Brielle

This is a solo work by the beloved Adam Young.

While it’s a stylish, modern pop song, the acoustic guitar and gentle, conversational vocals give it a slightly sad feel.

It’s especially likely to appeal to young women.

Goodbye Never Felt So BadJames Bay

James Bay – Goodbye Never Felt So Bad (Official Audio)

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.

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Time to Say GoodbyeAndrea Bocelli & Sarah Brightman

Andrea Bocelli, Sarah Brightman – Time To Say Goodbye (Live From Teatro Del Silenzio, Italy / 2007)

British soprano Sarah Brightman and former Italian tenor Andrea Bocelli perform a duet.

Released in 1996, this song became a worldwide hit and helped turn classical crossover into a global movement.

In Japan, Sarah Brightman’s music has been used as a news program theme, making it feel familiar to many.

StrawberryfireApples In Stereo

Apples In Stereo – Strawberryfire

As if awakening to Indian instruments like the Beatles in their Rubber Soul era, this band truly had a songwriting sense that could have taken over the world.

However, whether through bad luck or not, they are now effectively disbanded.

Listen to this song, and let yourself feel sad.

The RiverBruce Springsteen

Bruce Springsteen – The River (The River Tour, Tempe 1980)

A song influenced by Hank Williams’s “My Bucket’s Got a Hole in It.” Bruce Springsteen first performed this song at the “No Nukes” concerts at Madison Square Garden on September 21 and 22, 1979.