Saddest Western Songs Ranking [2025]

Small BumpEd Sheeran85rank/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.

How Do I Say GoodbyeDean Lewis86rank/position

Dean Lewis – How Do I Say Goodbye (Official Video)

A work by Dean Lewis known as a tearjerker.

Sparked by his father’s illness, the lyrics convey the anxiety and fear of facing a sudden farewell.

Filled with deep love and gratitude for family, the song was released in August 2022 and included on the album “The Hardest Love.” It resonates with those who have experienced parting from a loved one or who cherish family bonds.

Dean Lewis’s delicate vocals gently embrace listeners’ hearts and evoke empathy.

Fast CarTracy Chapman87rank/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.

Harvest MoonNeil Young88rank/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 SoldiersMartika89rank/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 Brightman90rank/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.

Moonlight Shadow ft. Maggie ReillyMike Oldfield91rank/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.