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 Newest Hits — (101–110)
Free FallingJames Arthur
James Arthur has led a turbulent life.
As a singer-songwriter from the UK, he won The X Factor in 2012 and drew widespread attention.
This track, included on his album Bitter Sweet Love released in January 2024, is a ballad that stirs deep emotions.
Arthur’s distinctive baritone voice poignantly conveys the search for self-worth and the anxiety of an uncertain future.
The song’s structure—beginning with a quiet piano accompaniment and gradually building—offers a compelling listen.
It’s a piece that gently stays by your side when you’re dealing with heartbreak or loneliness.
On a night you want to listen alone in silence, give it a try.
Happiest YearJaymes Young
A wonderful song that blends poignancy with warmth.
Released in January 2019 by Seattle-born James Young, this gem of a love song looks back on a lost romance while expressing gratitude.
James’s gentle vocals and emotional lyrics harmonize beautifully, resonating deeply with listeners.
Loved by many fans as a follow-up to his 2017 album “Feel Something,” this track is perfect for those trying to move forward despite heartbreak or for anyone who wants to cherish precious memories.
Queen Of DenmarkJohn Grant
It’s a song performed solo by John Grant.
The very minor-key, striking piano intro immediately draws you in.
The steady tempo and quiet delivery have a way of touching the heart.
It’s a ballad you can listen to at a relaxed pace.
Breaking PointLogan Michael
The music of American singer-songwriter Logan Michael has the power to leave a deep mark on listeners’ hearts.
Released in October 2023, this work captures the moment of a breakup swirling with intense anger and disappointment.
We catch a glimpse of the protagonist’s torment as he spends sleepless nights with whiskey, and his resolve to throw everything away pierces the chest.
Transcending the bounds of pop/rock, this song will resonate especially with those who have decided to part ways with strong conviction.
Try listening to it in whatever setting makes you feel most at ease—whether in your bedroom or on a drive.
I’ll Be Over YouTOTO
This is a song that drew a lot of attention as a ballad by a band famous for rock.
With its slow tempo and gentle mood far removed from rock, the melody makes it a very calming listen.
The music video, set against a sunset backdrop, also matches the impression of the song.
Tearjerkers! Heart-wrenching Western songs—from timeless classics to the latest hits—(111–120)
feel like shitTate McRae
Released in November 2021, the song by Canadian singer-songwriter Tate McRae is a poignant ballad that lays bare the pain of a breakup.
The protagonist’s struggle, still trapped in a past love, is vividly conveyed through Tate’s candid lyrics and moving vocals.
Issued as the lead single from her 2022 album “I Used to Think I Could Fly,” the track resonates deeply with listeners.
It’s highly relatable for those carrying similar emotional scars and is a perfect song for anyone seeking to heal from the pain of parting.
Now Is The HourThe 1975
A timeless, heart-stirring ballad has arrived from the UK’s The 1975.
Matthew Healy’s expressive vocals depict a profound longing for a lover far away.
Released in February 2024, the track also drew attention as part of the Apple TV+ series The New Look soundtrack.
Produced by Jack Antonoff, it rediscovers the allure of live instrumentation and delivers a fresh sound to listeners.
Resonating with anyone who has experienced long-distance love or a close parting, the song sings of hope for reunion.
With the warmth and depth of a piece that feels like a classic across eras, it reaffirms The 1975’s multifaceted talent.