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)
Leave Herd4vd
A song released in February 2024 by up-and-coming Texas singer-songwriter DeForVD.
It’s included on the album Withering.
The sound is marked by reverb-drenched guitar tones and a rock-inspired drum beat.
The lyrics explore the difficulty of clinging to past relationships and the need to discover a new self, expressing complex feelings toward an ex who reaches out in the middle of the night.
It’s a track that resonates with anyone facing heartbreak and a journey of self-discovery.
Not A Day Goes ByLonestar
The American country music band Lonestar released a single from I’m Already There in January 2002, a gem of a ballad that portrays profound sorrow and a sense of loss after losing a loved one.
Its gentle, resonant melody, rich harmonies, and deeply expressive vocals blend beautifully to convey both the pain of grief and the enduring love for someone dear.
The song touched many listeners, reaching No.
3 on the Billboard Hot Country Singles chart, and was nominated for Best Country Performance by a Duo or Group with Vocal at the 45th Annual Grammy Awards in 2003.
With its quietly consoling character, it has often been chosen to comfort those who have lost someone and for use in memorial settings—a heartwarming piece that offers solace.
Empty BenchDavid Kushner
A Christmas song filled with a profound sense of loss and aching longing has arrived from American singer-songwriter David Kushner.
After his breakout smash hit “Miserable Man,” his new track conveys the deep sorrow of losing a loved one through the symbolic image of an empty bench.
Teaming up with producer Rick Nowels, the song blends a bittersweet, melancholic atmosphere with Kushner’s deeply emotive vocals.
The music video, released in December 2024, racked up hundreds of thousands of views within days, capturing the hearts of many.
It’s a work that gently stands by those who find themselves alone during a season made for thinking of someone special.
Last NightMorgan Wallen
“Last Night” is a love song by Morgan Wallen, notable for its gentle vibe.
He achieved the rare feat for country music of debuting at No.
1 on the U.S.
albums chart with Dangerous: The Double Album.
In “Last Night,” the line “There’s no way that was the last night” leaves a strong impression, and the aching lyrics about not being able to let go of someone special tighten the chest.
If you’re going through a painful relationship, I hope listening to this song helps you get through it.
Yesterday Once MoreCarpenters
This classic song, which sings of love and nostalgia for music, is one of the Carpenters’ signature works, released in May 1973.
Created by the American brother-and-sister duo, it is imbued with deep affection and longing for pop songs of the 1950s and ’60s, beautifully balancing Karen Carpenter’s warm, tender vocals with Richard Carpenter’s delicate arrangements.
It reached No.
2 on the Billboard Hot 100 and became a worldwide hit.
It’s a must-listen for everyone who loves music—and for those moments when you want to look back on your youth.
Hate MeBlue October
A song by Justin Furstenfeld, the frontman of Blue October, about taking back his life and making amends to those he hurt through his drug addiction.
The track is notable for Justin’s very straightforward vocals, and the music video features his mother.
GeneradeBruno Mars
Generade means “hand grenade.” It’s a song that powerfully expresses a one-sided crush—the resolve to catch even a hand grenade for the sake of someone precious, to endure any pain.
When sung in Bruno’s voice, the sense of longing becomes even more poignant.