Saddest Western Songs Ranking [2026]

You Know You’re RightNirvana43rank/position

Nirvana – You Know You’re Right (LP Version)

A song recorded at Robert Lang Studios in Seattle on January 30, 1994, just before Nirvana embarked on their European tour.

It became the last song before Kurt Cobain’s death on April 5, 1994, and was released as a single eight years later.

Happiest YearJaymes Young44rank/position

Jaymes Young – Happiest Year [Official Music Video]

A song that portrays the feelings of someone who has experienced a broken heart, with a beautiful, heartrending melody that resonates deeply.

Looking back on a love that has ended, it sings of gratitude for the happiest moments.

Released in January 2019, the track is included on the album “Feel Something.” Jaymes Young’s clear, translucent vocals beautifully convey both the pain of heartbreak and the gratitude for the days spent together.

It’s a recommended song for those who have gone through a breakup and are struggling to sort out their feelings, or for anyone who wants to express gratitude to someone important.

Eyes ClosedEd Sheeran45rank/position

Ed Sheeran – Eyes Closed [Official Video]

A heart-stirring ballad that sings of longing for a beloved person who has been lost.

The gentle vocals seep into the heart, beautifully expressing the pain of loss that anyone can relate to.

Released in March 2023, the song was unveiled as the lead single from the album Subtract and achieved success on charts around the world.

Born from the experience of losing a friend, the lyrics are imbued with deep sorrow and nostalgia, offering comfort to listeners.

It’s a song I especially recommend to anyone who has lost someone dear or continues to hold someone in their heart.

Love Is a Losing GameAmy Winehouse46rank/position

Amy Winehouse – Love Is A Losing Game

This is an achingly poignant masterpiece by Amy Winehouse, the singer from England.

True to its title, “Love Is a Losing Game,” it sings of the futility of a love you know will never be rewarded, no matter how hard you try.

Even after giving everything, you’re left behind in the end, with a crushing sense of defeat and helplessness.

Anyone who’s worn themselves down in a barren, one-sided love will feel the sting of this hopeless situation all too well.

Her voice—deep and tinged with resignation—doesn’t console so much as it quietly stays beside the pain.

It’s a song that seeps into your heart on nights when you’re burdened with sorrow that has nowhere to go.

AlwaysDaniel Caesar47rank/position

Daniel Caesar – Always (Official Audio)

Have you ever wished happiness for someone you broke up with, while still holding unchanged feelings deep in your heart? This song, performed by Canadian singer-songwriter Daniel Caesar, gently accompanies that kind of complicated emotion.

Set to a quiet, dreamy sound, it portrays a protagonist who realizes that their love for the other person will never fade.

The track is included on the acclaimed album “NEVER ENOUGH,” released in April 2023, and in October 2023 he performed it on a popular American TV show.

If you feel pressured to forget and move on too quickly, quietly facing your emotions—like in this song—might actually lighten your heart and help you take a new step forward.

AngieThe Rolling Stones48rank/position

The Rolling Stones – Angie – OFFICIAL PROMO (Version 1)

Among the Rolling Stones’ many timeless classics, I think this is the one a lot of people like best.

Even recently, it was featured on a certain news program in connection with a divorce story.

Though it’s a sad song, it also gives a sense of hope for tomorrow.

It’s one of my personal favorites, too.

Wish You The BestLewis Capaldi49rank/position

Lewis Capaldi – Wish You The Best (Official Video)

A heartbreakingly sad piano ballad sung by Scottish singer-songwriter Lewis Capaldi.

You said, “I wish you happiness,” and broke up, even though you didn’t mean it—when deep down you wanted to stay by their side.

Haven’t you ever felt that kind of pain? This song delivers those unspoken truths and regrets with a voice that sounds like a cry from the soul.

The lyrics confess, “I said we should stay friends, but that was a lie,” and for anyone who’s been through a painful breakup, it may feel like the song speaks your feelings for you.

If you let yourself sink into the emotions you’ve kept buried deep in your heart and have a good cry, you might feel a little lighter.