Saddest Western Songs Ranking [2026]

Strange FruitBillie Holiday78rank/position

Billie Holiday – “Strange Fruit” Live 1959 [Reelin’ In The Years Archives]

This is a historic song by American legendary jazz singer Billie Holiday.

The shock I felt upon learning that the “strange fruit” in the title is a metaphor for Black people hanging from trees is beyond measure.

After an opening of piano that cuts through the silence, her voice—like it’s carving away at her soul—vividly depicts that terrifying scene.

This is not about the heartache of love; it’s a searing indictment of social injustice and a well of deep sorrow.

Intertwined with the epic hardships of her own life, her expression transcends mere music and seems to speak directly to the listener’s heart.

It’s a soul-shaking piece that can hardly be heard without tears.

Standing StillJewel79rank/position

Jewel – Standing Still (Official Music Video)

Jewel is a singer-songwriter from the United States, and her debut album, Pieces of You, sold 12 million copies.

This song was released as a single from the 2001 album This Way.

It was featured in the American teen drama Dawson’s Creek and became a big hit.

cecilia and the satelliteAndrew McMahon80rank/position

Andrew McMahon in the Wilderness – Cecilia And The Satellite

It’s included on “In the Wilderness,” the solo album by Andrew McMahon, the vocalist of Something Corporate.

It was released in 2014.

After overcoming leukemia and making his comeback, Andrew welcomed a daughter in 2013.

It’s said that he wrote this song for his beloved daughter.

the way things gobeabadoobee81rank/position

beabadoobee – the way things go

Beabadoobee is a British singer-songwriter.

While she excels at ’90s alternative rock and dream pop, “the way things go” is a ballad that portrays a heartbroken woman looking back on the past and letting her unresolved feelings build up.

Her high, airy vocals convey that bittersweet state of mind without holding anything back.

It’s also a song about long-distance love, so those who’ve experienced it may find it especially relatable.

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BrielleSky Sailing82rank/position

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.

Across The UniverseFIONA APPLE83rank/position

Fiona Apple – “Across The Universe”

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.

Spanish SaharaFoals84rank/position

Foals – Spanish Sahara [OFFICIAL VIDEO]

A song from Total Life Forever, the second album by the British indie rock band Foals.

It premiered on BBC Radio 1 on March 1, 2010.

The track was selected by NME as the best track of 2010.