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)
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.
Tearjerkers! Heart-wrenching Western Songs — From Timeless Classics to the Newest Hits — (121–130)
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.
The FlameCheap Trick
A soft ballad included on the 1988 album Lap of Luxury.
Written by the songwriting team of Bob Mitchell and Nick Graham, the song was originally penned for the British singer Elkie Brooks.
It became Cheap Trick’s only No.
1 hit on the charts.
Wake Me Up When September EndsGreen Day
This is a song about a country boy who becomes an American volunteer soldier.
Also, the title means “Wake me up when September ends,” which indirectly alludes to the 9/11 attacks and strongly expresses an anti-war stance.
No AirJordin Sparks ft. Chris Brown
A song about a dying relationship produced by the R&B/pop producer duo The Underdogs, who are also known for their work on the Dreamgirls soundtrack.
It’s a duet by Jordin Sparks and her labelmate Chris Brown, and it spent seven weeks at No.
1 on the New Zealand singles chart.
Please Don’t Fall In Love With MeKhalid
This song stands out for its poignant lyrics and a melody that really seeps into the heart.
Khalid, an American artist, weaves a story drawn from his own experiences, inviting listeners on a journey through love, loss, and self-discovery.
The arrangement, which samples an Alicia Keys classic, is excellent and reads as a thoughtful homage to R&B’s heritage.
Released in April 2024, the track signals the beginning of a new musical chapter for Khalid.
Anyone who’s been hurt by past relationships will likely relate.
It’s the perfect song for quiet nights alone or reflective rainy-day drives.
How Am I Supposed To Live Without YouMichael Bolton
This song, styled after 1960s–70s soul music and lamenting the loss of a lover, was written by Michael Bolton and Doug James.
It was originally offered to Air Supply, but because the executive producer wanted changes to the chorus and Bolton refused, it has been placed on indefinite hold.