[Masterpiece] Tear-jerking Western songs. The tears won’t stop… truly sad songs [2025]

All My Happiness Is GonePurple Mountains

Purple Mountains “All My Happiness is Gone” (Official Music Video)

Set to a breezy country-rock melody, it somehow makes your chest tighten.

That strange sensation is exactly what this song by the American unit Purple Mountains evokes.

When the central figure, David Berman, sings “All my happiness is gone,” it feels less like a lyric and more like his very soul.

Knowing that this became his final work, the upbeat sound only throws its deep sorrow into sharper relief.

It may be an achingly honest confession, borrowing the form of music.

When you brush against that inescapable loneliness, the tears start flowing and won’t stop.

Strange FruitBillie Holiday

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.

Only Love Can Break Your HeartNeil Young

Only Love Can Break Your Heart

This is a classic song by Canadian singer-songwriter Neil Young that quietly portrays the pain of heartbreak.

It’s said to have been written with his bandmate Graham Nash’s painful breakup in mind.

The universal message in the title—“In the end, only love can break your heart”—pierces deeply into the soul.

That helpless sense of loss when you lose someone precious—many of us know it all too well.

Neil Young’s delicate, fragile voice and the gentle acoustic tones softly cradle a wounded heart.

It’s a song that carries a warm reassurance, as if to say, “You’re not alone,” offering quiet comfort.

Someone Like YouAdele

Adele – Someone Like You (Official Music Video)

This is a gem of a ballad sung by Adele, a singer-songwriter from the UK, that brought tears to listeners around the world.

It’s based on her own real-life experience of learning that her ex had found someone new.

The lyrics, which bravely claim “I’ll find someone like you” while her heart cries out “It isn’t over for me yet,” are so honest they make your chest tighten.

That complicated state of mind—holding painful lingering feelings yet trying to wish the other person happiness—is something anyone who’s been through a hard breakup can’t help but relate to.

Listening to this song may bring back memories of a love you can’t forget.

Her soulful voice etches that sorrow even more deeply into the heart.

Love Is a Losing GameAmy Winehouse

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.

Time After TimeCyndi Lauper

Cyndi Lauper – Time After Time (Official HD Video)

Released in 1983 on Cyndi Lauper’s album She’s So Unusual, it was issued as a single the following year, in 1984.

It reached No.

1 in the U.

S.

and has been covered by many famous artists, including Miles Davis.

It’s So Hard to Say Goodbye to YesterdayBoyz II Men

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.