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 Songs in Western Music — From Timeless Classics to the Newest Hits — (31–40)
Adore YouHarry Styles

Harry Styles, a member of One Direction who also enjoys worldwide popularity as a solo artist.
This track, included on his December 2019 album Fine Line, perfectly blends a ’70s-style groove with a contemporary pop sensibility.
The lyrics, which express deep love and devotion for another, gently stay close to a lonely heart and wrap it in warmth.
The song has been widely embraced in many contexts, including its inclusion in the game Just Dance 2021.
The music video—like a film set on a fictional island—is also a must-see.
Give it a listen on nights when you want someone to affirm you, or when you’d like to quietly let your emotions out and have a good cry.
If I die youngThe Band Perry

It begins with the opening line, “If I were to die young…” When I first heard it, I was surprised that a song like this existed.
It has a relaxed, upbeat country feel, but the lyrics—the heart of the song—reflect on life and on life and death.
you were good to meJeremy Zucker & Chelsea Cutler

From the fact that the title is in the past tense, you can already sense the end of a relationship.
It’s a song released in 2019 by rising talent Jeremy Zucker from New Jersey, USA.
The track features guest vocals from Chelsea Cutler, the female singer known for her work on a Kygo track, and the interplay and harmonies between the two are truly beautiful.
Jeremy is an artist who blends electronic and acoustic elements, but this time he captivates with an organic, piano-centered sound kept to a minimum number of layers.
The lyrics depict what is likely a relationship between lovers that has come to an end; even as they try to look forward, the bittersweet inner landscapes they each carry are portrayed with a poignant, melancholic atmosphere.
Say You Won’t Let GoJames Arthur

James Arthur, whose tattoo-covered look is striking, is a maverick singer-songwriter with a tumultuous past: he rose to fame as a musician, was knocked to rock bottom by scandal, and then clawed his way back to success.
His 2016 release “Say You Won’t Let Go” became the song that put his career back on track—a folky ballad that topped the UK charts.
Its very simplicity gives it a universal appeal; it’s a straightforward love song that leaves listeners feeling bittersweet yet warm.
It isn’t exactly sad, but its heartfelt melody and vocals are sure to bring a tear to your eye.
No OneAlicia Keys

Alicia Keys has a very husky, distinctive voice that becomes addictive.
The song condenses a sparkling melody and a richly crafted world.
She also appears in the music video herself, and her stunning looks are a highlight as well.


