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! Heart-wrenching Western Songs — From Timeless Classics to the Newest Hits — (121–130)
I’ll Be Over YouTOTO
This is a song that drew a lot of attention as a ballad by a band famous for rock.
With its slow tempo and gentle mood far removed from rock, the melody makes it a very calming listen.
The music video, set against a sunset backdrop, also matches the impression of the song.
D-I-V-O-R-C-ETammy Wynette
This poignant country song, which became a No.
1 chart hit by Tammy Wynette, was written by the songwriting duo Robert Valentine “Bobby” Braddock and Claude “Curly” Putman Jr.
It is sung from a woman’s perspective about divorce.
feel like shitTate McRae
Released in November 2021, the song by Canadian singer-songwriter Tate McRae is a poignant ballad that lays bare the pain of a breakup.
The protagonist’s struggle, still trapped in a past love, is vividly conveyed through Tate’s candid lyrics and moving vocals.
Issued as the lead single from her 2022 album “I Used to Think I Could Fly,” the track resonates deeply with listeners.
It’s highly relatable for those carrying similar emotional scars and is a perfect song for anyone seeking to heal from the pain of parting.
Now Is The HourThe 1975
A timeless, heart-stirring ballad has arrived from the UK’s The 1975.
Matthew Healy’s expressive vocals depict a profound longing for a lover far away.
Released in February 2024, the track also drew attention as part of the Apple TV+ series The New Look soundtrack.
Produced by Jack Antonoff, it rediscovers the allure of live instrumentation and delivers a fresh sound to listeners.
Resonating with anyone who has experienced long-distance love or a close parting, the song sings of hope for reunion.
With the warmth and depth of a piece that feels like a classic across eras, it reaffirms The 1975’s multifaceted talent.
Run To YouWhitney Houston
It’s a song used in part of the movie The Bodyguard, in which Whitney Houston herself appeared.
The film’s theme song is I Will Always Love You, and both songs are quite poignant.