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—(111–120)
Car’s OutsideJames Arthur
A ballad that stays close to the hearts of those carrying bittersweet feelings—that’s James Arthur’s music.
Released in October 2019, this song explores the difficulties of a long-distance relationship, poignantly expressing the loneliness of living apart from the one you love.
Arthur, a UK native, delivers a vocal performance that is both powerful and delicate, resonating deeply with listeners.
Through the lyrics, the protagonist’s inner struggle—forced into frequent travel—and their earnest wish to be with their loved one come vividly to life.
It’s a song I especially recommend to anyone who has experienced a breakup or is pained by the distance separating them from someone important.
Tearjerkers! Heart-wrenching Western Songs — From Timeless Classics to the Newest Hits — (121–130)
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.
Fingers CrossedLauren Spencer Smith
The song that captured global attention in 2022 is a poignant ballad by Canadian artist Lauren Spencer Smith.
It spread rapidly on TikTok and sparked a huge response worldwide, topping the charts in countries like Ireland and Norway.
The track portrays the pain of a betrayed love.
The expression “crossing fingers” is especially striking, symbolizing the hollowness of love’s promises.
Spencer Smith’s soaring vocals beautifully convey the frustration and heartache of a breakup.
The song is included on her debut album, Mirror, released in July 2023, and it resonates deeply with anyone who has endured the bitter side of love.
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.
Don’t Forget MeMaggie Rogers
The song released in February 2024 reveals a new side of American singer-songwriter Maggie Rogers.
Set to a sound that skillfully blends folk and pop, the lyrics vividly capture the joy and unease she feels through a friend’s wedding, as well as her own views on love.
The line “Love me, but when it’s time to go, don’t forget me” conveys complex emotions that are sure to resonate with many listeners.
It’s a track that makes you want to blast it in the car, evoking the start of a new season.
Especially recommended for those standing at a turning point in life.