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! Heart-wrenching Western songs — from timeless classics to the latest hits — (51–60)
I Eat DinnerRufus Wainwright feat. Dido
Rufus Wainwright’s singing amplifies the feeling of heartbreak to the utmost.
The melody is very quiet, overflowing with a truly sorrowful ballad-like atmosphere.
The lyrics, written about the grief of losing a loved one, make it an incredibly poignant song.
ImaginationShawn Mendes
Shawn Mendes, the Canadian singer-songwriter who’s won popularity with his sweet looks and catchy musical style.
This is a hidden gem included on the deluxe edition of his debut album, Handwritten, which drew attention when he was 16.
The song revolves around an achingly sad unrequited love: being unable to confess your feelings to the person you like and becoming their lover only in your imagination.
His crystalline vocals and the gentle tones of the acoustic guitar portray the protagonist’s pure, single-minded feelings, tightening your chest.
Released in April 2015, this emotional track is one you’ll want to hear if you’re holding onto a love you know will never come true.
Out of LoveAlessia Cara
Alessia Cara, a Canadian singer-songwriter who has earned strong support from many listeners by expressing human emotions straightforwardly.
Her song “Out of Love” also conveys, in a direct way, the feelings of a woman who has broken up with her boyfriend, paired with a melody imbued with quietude.
I Don’t Think That I Like HerCharlie Puth
When it comes to songs that capture the bittersweetness of love, you can’t leave out the work of American artist Charlie Puth.
Released in September 2022, this piece brilliantly conveys the pain of heartbreak and the anxiety of new love.
Puth’s clear, pure vocals and a melody that sinks into the heart resonate deeply with listeners.
The song portrays the complex emotions of a man worn out by dating games, taking a step back—and it’s something anyone who’s experienced heartbreak can relate to.
How about listening to it slowly in your bedroom and taking some time to face your feelings?
EverytimeBritney Spears
Britney has quite a few intense tracks, but this one is a relaxed ballad.
It’s also a heartbreak song that expresses the complex feelings of loving someone who won’t look your way.
I think it’s one of those songs that reaffirms that Britney really does have vocal prowess.