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—(21–30)
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.
Say SomethingA Great Big World ft. Christina Aguilera
It’s a song featured in the film “If I Stay.” It’s unbearably heart-wrenching, and just listening to it makes me feel like I’m about to burst into tears.
A Great Big World came to Japan in 2015, and at that time they collaborated with May J.
on this song.
Tearjerkers! Heartbreaking Songs in Western Music — From Timeless Classics to the Newest Hits — (31–40)
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.
The One That Got AwayKaty Perry
When it comes to Katy, I think she usually has a lot of positive, up-tempo songs, but this one is a heart-breaking track and feels unusual.
The tempo is definitely Katy-like and upbeat, but the song’s theme is about a widow.
Listening to it together with the music video makes it even more poignant.
HurtChristina Aguilera
This song makes you realize that it’s not easy to get back what you’ve lost.
What really mattered, what truly made you happy.
It conveys that unbearable, irreparable feeling of having hurt someone, and Christina’s powerful vocals resonate deep in your chest.
Let her goPassenger
It’s a breakup song about her.
It makes you think that you mustn’t take the happiness right in front of you for granted.
You might feel you don’t need the sun when it’s hot, but when it’s cold you realize you do.
I think it’s a song that makes you reflect not only on love, but on life as well.
Wrong DirectionHailee Steinfeld
Hailee Steinfeld, who shot to fame as a prodigy child actress after winning numerous awards for her role as the young girl in the 2010 film True Grit, directed by the Coen Brothers with Steven Spielberg as executive producer, is rapidly gaining popularity in Japan as a rising young actress—and she also has a career as a singer.
Her song Wrong Direction was released in January 2020, and Hailee herself is credited as one of the songwriters.
With lyrics that lay bare piercing emotions, a melody that swells from a whispering intro into something deeply emotional, and an arrangement that seems to echo those feelings, it’s a beautifully melancholic ballad that clearly showcases her skills as a singer-songwriter.
It’s said to be about her breakup with Niall Horan, and if that’s the case, the word “Direction” in the title feels particularly loaded with meaning.