[Masterpiece] Tear-jerking Western songs. The tears won’t stop… truly sad songs [2026]

Tears In HeavenEric Clapton

Eric Clapton – Tears In Heaven (Official Video)

A song written by Clapton and Will Jennings about Clapton’s four-year-old son, Conor, who died after falling from the 53rd floor of an apartment building on March 20, 1991.

It won Grammy Awards in 1993 for Record of the Year, Song of the Year, and Best Male Pop Vocal Performance.

See You Again ft. Charlie PuthWiz Khalifa

Wiz Khalifa – See You Again ft. Charlie Puth [Official Video] Furious 7 Soundtrack

It was released as an insert song for the blockbuster film Fast & Furious.

The performers are rapper Wiz Khalifa and the rapidly rising Charlie Puth.

Many listeners burst into tears, saying that when they hear the song, it reminds them of Paul Walker, the lead actor who died suddenly in an accident before the film was completed.

Wish You The BestLewis Capaldi

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.

Depression (feat. Coconut Records)Ben Kweller

Depression (feat. Coconut Records)

Have you ever experienced the kind of despair that feels like all the color has drained from the world after suddenly losing a beloved family member? “Depression” by American singer-songwriter Ben Kweller is a song that lays bare his feelings for his son, who died in a car accident.

The fact that he wrote it while listening to recordings his son left behind conveys, almost painfully, the heart-rending ache and deep love he feels as a father.

His voice, singing without hiding his despair, is sure to offer comfort to those carrying similar pain.

This song, which strives to find light from the depths of sorrow, may give you the strength to move forward.

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.

Summertime SadnessLana Del Rey

Lana Del Rey – Summertime Sadness (Official Music Video)

“Summertime Sadness,” a signature song by American singer-songwriter Lana Del Rey.

It’s an achingly beautiful track that sings of the radiant days of summer and the sense of loss brought on by a friend’s tragic end.

Lana Del Rey’s languid, dreamlike vocals match the song’s melancholic atmosphere perfectly.

The chorus, pleading “Kiss me hard before you go,” feels like the climax of a tragic film.

As you listen, happy memories resurface even as you’re confronted with the reality that there’s no going back—you may find yourself unable to hold back tears.

You Break Me FirstTate McRae

Tate McRae – you broke me first (Official Video)

This is a heartbreak song by Canadian singer-songwriter Tate McRae that holds both strength and fragility.

It portrays the cold yet sorrowful feelings when an ex who once hurt you reaches out only when it’s convenient for them.

The line “You’re the one who broke me first” pushes them away, squeezing your chest as you hear it.

Behind those searing words, it feels as if there’s a deep sadness so intense that without saying them, her heart might fall apart.

For anyone who’s been through a painful love, it may resonate with that moment when you put on a brave face to protect yourself.

Her delicate vocals riding over a quiet beat gently wrap around that pain and bring you to tears.