Songs That Make You Cry: Heart-Wrenching Western Music—from Timeless Classics to the Newest Hits
There are times when, instead of listening to music to get pumped up or fired up, you deliberately want to listen to poignant or slightly sad songs and have a good cry alone, right?
Upbeat tracks that give you a push are great, but in this article we’ve researched and selected timeless, heart-wrenching English-language songs that empathize with listeners’ feelings, both old and new.
From classic standards to recent hits and the latest buzzworthy tracks, we’re bringing you a genre-crossing selection.
Try listening in whatever setting makes you feel most at ease—whether that’s in your bedroom or on a drive!
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Tearjerkers! Heartbreaking Western Songs — From Timeless Classics to the Newest Hits — (71–80)
SmileMorgan Wallen
American singer-songwriter Morgan Wallen’s new song is making waves.
Surprise-released in December 2024, the track is a poignant ballad that looks back on a past relationship.
Sparked by a smiling face in a photograph, the lyrics stir nostalgia for a love that’s been lost.
Wallen’s emotive vocals and a sound that blends country and pop are especially compelling.
Fans are also looking forward to its debut at his first-ever festival slated for 2025.
It’s a perfect song for when you’re in the mood to sink into old memories.
How can you mend a broken heartBee Gees
A song that became the Bee Gees’ first No.
1 hit on the U.S.
charts.
It’s also known as a song Robin Gibb wrote effortlessly in about an hour.
Al Green covered it in 1972 on his album “Let’s Stay Together,” and his version was used in the 1999 film “Notting Hill.”
I Can’t Make You Love MeBonnie Raitt
A song written by songwriters Mike Reid and Allen Shamblin.
Reid got the idea for the song from a newspaper article about a man who, while drunk, shot his girlfriend’s car.
It is sung from the perspective of a woman who knows that the person she loves is no longer interested in her.
CryingRoy Orbison
A song depicting a reunion that came too late with a woman he still loves.
It carries the message that crying is not a weakness but a sign of sensitivity.
The song was begun by Roy Orbison for a country singer named Don Gibson, and its working title was “Once Again.”
Wish You The BestLewis Capaldi
Lewis Capaldi is a singer-songwriter from Scotland.
His 2018 single “Someone You Loved” drew attention for reaching No.
1 on the U.S.
singles chart—a rare achievement for a Scottish artist.
And his 2023 release “Wish You The Best” is a love song with a strikingly poignant chorus that says, “I don’t want to be away from you.” It’s an incredibly moving track that might just bring you to tears.
ou’re The Best ThingThe Style Council
Since it was a hit in Japan as well, I think many people know this classic.
It has a distinctly mature vibe.
The Style Council’s sweet vocals match the pop melody, so it doesn’t really come across as a ballad.
Love Is a Losing GameAmy Winehouse
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.