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 Newest Hits — (71–80)
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 YoursJason Mraz
It sounds like a bright and upbeat melody.
With its brisk tempo, it feels like a song that could lift your spirits.
The relatively high male vocals match beautifully with the clean guitar melody.
It’s a song I’d love people who are feeling down to listen to.
The LovedPaul Weller
The performance is a solo singing with a deep, husky voice, and it sounds really cool.
As the title suggests, it’s a heartbreak ballad.
The tempo gradually picks up, and as you listen, it even feels like a song that somehow lifts your spirits.
Tearjerkers! Heart-wrenching Western songs — from timeless classics to the latest hits — (81–90)
California King BedRihanna
It’s a mellow ballad by Rihanna, an artist renowned for working across a wide range of genres like R&B and soul.
Her powerful, clear vocals match the melody perfectly, making it a song that truly resonates with the heart.
Eternal FlameThe Bangles
It seems it was released in Japan under the title “A Full Heart of Love.” The Bangles are a four-woman girls’ band, and their gentle, feminine melodies are really wonderful.
Pay attention to the cute singing voice of the vocalist, Susanna Hoffs.
The Wind Cries MaryThe Jimi Hendrix Experience
A song that Jimi Hendrix was inspired to write by his then-girlfriend, Kathy Mary Etchingham.
They argued about her cooking, and in anger she started throwing pots and pans, then eventually left to spend the night at a friend’s place.
There’s a story that when she came back, Jimi had written The Wind Cries Mary for her.
Die For You (Remix)The Weeknd & Ariana Grande
Die For You (Remix) is also known for going viral on TikTok.
It’s a track The Weeknd created together with Ariana Grande—a remix of The Weeknd’s 2016 release Die For You.
The lyrics portray a deep love, expressing a willingness to do anything for the other person.
While there are a few slightly explicit expressions, they also convey the depth of that affection.
