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!
- [2026] Moving Western songs that touch the heart: A roundup of recommended classics
- Top Tearjerker Western Songs Ranking [2026]
- Western songs about saying “goodbye” — perfect for bereavement or a departed lover
- Hidden gems of tear-jerking Western songs. Recommended popular tracks.
- 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
- When you’re hurting and feel like you want to disappear… timeless Western songs to listen to at times like these
- Emotional Western Music Special | Handpicked from All Generations
Tearjerkers! Bittersweet Western Songs — From Timeless Classics to the Newest Hits — (151–160)
RainMadonna
It’s a song with a very distinctive and mysterious melody.
It has become one of Madonna’s signature ballads and is a classic that everyone knows.
In the music video, the renowned pianist Ryuichi Sakamoto even appears in the role of a director.
CirclesPost Malone
I think it’s hard to catch the lyrics of songs in English.
With this song, “Circles,” many people might feel it sounds bright if they just listen to the melody.
The vibe is upbeat, but in fact it’s a song about losing someone important.
Please give it a listen.
What Hurts The MostRascal Flatts
A song with the message “Don’t wait to tell someone how you feel; don’t hold back your feelings.” It was originally first recorded in 2003 by country singer Mark Willis.
This Rascal Flatts version reached No.
1 on the Country and Adult Contemporary charts in 2006.
How Do You Sleep?Sam Smith
“How Do You Sleep?” is striking for its explosive, emotion-laden melody.
The song portrays the fragile feelings of a man being lied to by his lover.
Its serious melody accentuates the rawness of the lyrics.
It may bring you down, but it’s a real tearjerker.
Don’t need you toSamantha Mumba
This is a song featured in the film Legally Blonde 1.
The protagonist, Elle, is relentlessly positive, cheerful, and fiercely competitive.
I think this song portrays a strong woman who also shows glimpses of vulnerability, much like Elle.
It also conveys a woman’s desire for love to be shown through actions, not just words.
Heaven’s Only Days Down The RoadShelby Lynne
Shelby Lynne went through a tragic experience in 1986 when her father shot and killed her mother.
She and her sister, singer Allison Moorer, were left orphaned and lived with relatives.
Twenty-five years later, she wrote the song “Heaven’s Only Days Down the Road” from her father’s perspective after the fact.
Tearjerkers! Heartbreaking Western Songs — From Timeless Classics to the Latest Hits — (161–170)
PerfectSimple Plan
It’s a song that expresses the complicated feelings of adolescence—knowing I’m not perfect and feeling sorry toward my parents.
I think the reason Simple Plan resonates so well with teenagers is that they directly capture these uniquely adolescent emotions in their music.
I discovered this song when I was in middle school and listened to it all the time.