Saddest Western Songs Ranking [2026]

Fast CarTracy Chapman36rank/position

Tracy Chapman – Fast Car (Official Music Video)

This is a signature song by American singer-songwriter Tracy Chapman.

Wanting to escape a life of poverty, they pin their hopes on a single fast car.

Her deep, slightly melancholic voice weaves this heartfelt story.

They set out believing in hope, yet reality proves unbearably harsh, and the rift with their partner only widens.

It’s easy to empathize with the loneliness of feeling like you’re the only one struggling desperately, isn’t it? The modest wish to “be somebody someday” crumbles so painfully and fleetingly that it tightens your chest.

If you immerse yourself in the story while listening to this song, its helplessness may bring you to tears.

Small BumpEd Sheeran37rank/position

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.

Harvest MoonNeil Young38rank/position

Neil Young – Harvest Moon [Official Music Video]

In Japan, the Beatles and Eric Clapton are popular, but Neil Young hasn’t reached that level.

I find that personally very disappointing.

This masterpiece has a touch of sadness, yet it’s purely a wonderful song.

Toy SoldiersMartika39rank/position

Martika – Toy Soldiers

Released in 1989 by American singer-songwriter Martika, it reached number one on the Billboard chart.

She didn’t have subsequent hits and was half-forgotten, but in 2004 the song returned to the spotlight when Eminem sampled it.

Time to Say GoodbyeAndrea Bocelli & Sarah Brightman40rank/position

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.

Tears In HeavenEric Clapton41rank/position

Eric Clapton – Tears In Heaven (Official Video)

A song written by Clapton and Will Jennings about Clapton’s four-year-old son, Conor, who died after falling from the 53rd floor of an apartment building on March 20, 1991.

It won Grammy Awards in 1993 for Record of the Year, Song of the Year, and Best Male Pop Vocal Performance.

Moonlight Shadow ft. Maggie ReillyMike Oldfield42rank/position

Mike Oldfield – Moonlight Shadow ft. Maggie Reilly

It was released in 1983 by British musician Mike Oldfield.

The lyrics tell a poignant story about meeting a murdered lover again in heaven someday.

Although there were rumors that it was inspired by John Lennon’s assassination, Mike, who wrote the lyrics, has firmly denied this.

It became a huge hit across Europe.