Saddest Western Songs Ranking [2026]

RetrogradeJames Blake64rank/position

James Blake – Retrograde

James Blake, who grew from a young rising star of post-dubstep into a singer-songwriter emblematic of his era.

This track is included on his second album, Overgrown, released in 2013.

Written right after a fight with his girlfriend, the song beautifully conveys the complex feelings he had toward her and the realizations that came with the break of dawn.

It’s not exactly a breakup song, but perhaps the sense of sorrow we feel comes from the sound and his voice…

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I Always Wanna Die (Sometimes)The 197565rank/position

I Always Wanna Die (Sometimes)

As of 2020, all three albums they had released had reached No.

1 on the UK charts, making THE 1975 a band at the top both in name and in reality.

This track, which closes their third album released in 2018, A Brief Inquiry into Online Relationships, is, within their genre-spanning sound, a fairly simple rock ballad.

Its startling title carries a characteristically British, paradoxical nuance, and even amid sorrow and resignation, you can sense a subtly ironic kind of optimism.

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Against All OddsPhil Collins66rank/position

Phil Collins “Against All Odds”

It was released in 1984 by British musician Phil Collins.

Used as the theme song for the film “Against All Odds,” it reached No.

1 in the United States.

This is the biggest hit among his released songs.

With this track, he won the Grammy Award for Best Male Pop Vocal Performance in 1985.

F**k it I love youLana Del Rey67rank/position

Lana Del Rey – Fuck it I love you / The greatest

A standout singer-songwriter from New York, Lana Del Rey released this track on her August 2019 album Norman Fucking Rockwell!.

While many of her songs express sadness, this piece—despite its seemingly aggressive title—also carries a melancholy tone and an overall wistful atmosphere.

Many listeners will relate to Lana’s lyrics, which intertwine her journey of leaving her hometown in pursuit of success for California with her feelings for the man she loves.

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It’s So Hard to Say Goodbye to YesterdayBoyz II Men68rank/position

Boyz II Men – It’s So Hard To Say Goodbye To Yesterday

After parting with someone dear, have you ever felt your chest tighten with the thought that you can never return to the joyful “yesterday”? The song “It’s So Hard to Say Goodbye to Yesterday” by the American R&B group Boyz II Men is a classic that sings of longing for the past and the pain of farewell.

Precisely because it’s performed a cappella, without any instruments, the warmth and poignancy of their voices seep directly into the heart.

It’s as if the beautiful harmonies gently embrace the sorrow that overflows no matter how hard you try to hold it back.

This song feels like a warm presence that quietly stays close to a heart that has experienced a painful parting, allowing the tears to flow.

Don`t dream it`s overSixpence None The Richer69rank/position

Sixpence none the richer – Don`t dream it`s over (official video)

They’re a band formed in Texas, USA.

The vocals by Leigh Nash resonate with a poignant, bittersweet quality.

The original is by Crowded House, but since this version was used as the theme song for an NHK program in Japan, it may be the more familiar one there.

Birthday CakeDylan Conrique70rank/position

Dylan Conrique – Birthday Cake (Official Music Video)

A poignant song born from the experience of losing a friend’s mother at the age of 47.

Rather than being crushed by grief, it urges us to live life to the fullest—the way the departed would have wanted.

Dylan Conrique’s crystalline vocals carry a powerful message that finds hope even within sorrow.

Released in February 2022, this work showcases the full talent of the 19-year-old artist from California.

It’s a song that offers comfort to those who have lost someone dear or who stand at a crossroads in life.