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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Tear-Jerking! Heartbreaking Songs in Western Music — From Timeless Classics to the Newest Hits — (91–100)
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.
You Break Me FirstTate McRae
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.
I’m Not Gonna Miss YouGlen Campbell
Glen Campbell revealed in 2011 that he was battling Alzheimer’s disease.
This song is the last piece he wrote with Julian Raymond.
Inspired by his struggle with Alzheimer’s, it serves as a message to his wife and children.
Wake Me Up When September EndsGreen Day
This is a song about a country boy who becomes an American volunteer soldier.
Also, the title means “Wake me up when September ends,” which indirectly alludes to the 9/11 attacks and strongly expresses an anti-war stance.
Crying My Eyes OutStephen Puth
For those who want to listen to a tear-jerker but aren’t into songs that feel too heavy, Crying My Eyes Out is highly recommended.
The lyrics are crafted to be sad, but the melody is an easy-to-listen-to, electro-infused pop sound.
Show Me The Meaning Of Being LonelyBackstreet Boys
The poignant ballad by the American group Backstreet Boys is a moving song themed around heartbreak and loneliness.
Featuring beautiful strings and a wistful melody, the members’ emotive vocals strike a chord.
Included on the May 1999 album “Millennium,” it was released as a single in December of the same year.
It became a global hit, reaching as high as No.
6 on the Billboard Hot 100.
As a song that offers solace to those grappling with a sense of loss, it continues to be beloved by many listeners today.
Tears can be so softChristine&the Queens
Héloïse Letissier, a singer who represents France.
Under her solo project name, Christine and the Queens, she released Tears can be so soft.
It explores themes of loneliness and sorrow, with lyrics that portray a yearning to see one’s family.
As you listen, pay attention to the eerie yet wistful sound built on string instruments.
By the way, the stylish music video was filmed in Los Angeles.
