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 Latest Hits — (41–50)
BreakevenThe Script
A single released in 2008 by the Irish pop-rock band The Script.
It reached No.
10 on the Irish charts and No.
3 in Australia, and also hit No.
1 on Billboard’s Adult Pop chart.
Anywhere I Lay My HeadTom Waits
A song depicting a man who longs for the joyful days he sees others enjoying.
It is sung by Tom Waits, an American singer-songwriter and actor.
The song is also known for being recorded by actress Scarlett Johansson as the title track of her 2008 album.
You & IOne Direction
Speaking of One Direction, I always had the impression they had lots of poppy, catchy melodies that make you feel energized when you listen.
But they’ve also released such a gentle, tender ballad.
It’s a refreshing, easy-to-listen-to ballad.
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.
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.
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.
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.