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!
- Top Tearjerker Western Songs Ranking [2026]
- Western songs about saying “goodbye” — perfect for bereavement or a departed lover
- When you’re hurting and feel like you want to disappear… timeless Western songs to listen to at times like these
- Hidden gems of tear-jerking Western songs. Recommended popular tracks.
- [2026] Moving Western songs that touch the heart: A roundup of recommended classics
- Top Cry-Inducing Western Songs Ranking [2026]
- Beautiful, lovely Western music. A roundup of recommended classic songs.
- Top 2026 Rankings of Melancholic Western Songs
- A Collection of Heart-Touching Western Ballads — From Classics to the Newest Hits
- Really dark... Classic Western songs | So dark that it may trigger depression—proceed with caution!
- Western songs used in commercials — tear-jerking classics and popular tracks
- A collection of emotionally resonant dark-themed Western songs—tracks with lyrics that deeply echo in the heart
- Emotional Western Music Special | Handpicked from All Generations
Tearjerkers! Heartbreaking Western Songs — From Timeless Classics to the Latest Hits — (41–50)
Lost In Your EyesDebbie Gibson

It seems that the artist singing this song, Debbie Gibson, was also active as an actress.
Her clear soprano voice matches the bright piano melody very well.
Apparently, she also plays the piano herself.
Whatcha sayJason Derulo

This is the song that became famous during the well-known Tiger Woods cheating scandal.
Jason Derulo is said to have composed the song himself while imagining Woods.
Jason also made his debut with this track.
At first, his dancing wasn’t very good, but now he moves like a professional dancer.
Tears In HeavenEric Clapton

Eric Clapton is a legendary singer-songwriter and guitarist whose name is etched in music history, continually creating timeless songs loved across generations.
“Tears in Heaven,” distinguished by its warm fingerpicked acoustic guitar and the mellow tone of a fretless acoustic bass, was released in 1992.
It became a hit as the theme song for the film Rush and is one of Clapton’s signature tracks, even earning a Grammy nomination.
The story behind the song is deeply sorrowful: Clapton wrote it in 1991 as a tribute to his young son, who tragically passed away in an accident.
With that in mind, reading the lyrics while listening to the song evokes the image of Clapton striving to overcome tragedy and move forward—something that is sure to bring listeners to tears.
BreakevenThe Script

A single released in 2008 by the Irish pop-rock band The Script.
It reached No.
10 on the Irish charts and No.
3 in Australia, and also hit No.
1 on Billboard’s Adult Pop chart.
You & IOne Direction

Speaking of One Direction, I always had the impression they had lots of poppy, catchy melodies that make you feel energized when you listen.
But they’ve also released such a gentle, tender ballad.
It’s a refreshing, easy-to-listen-to ballad.


