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 Songs in Western Music—from Timeless Classics to the Newest Hits—(141–150)
Happiest YearJaymes Young
A wonderful song that blends poignancy with warmth.
Released in January 2019 by Seattle-born James Young, this gem of a love song looks back on a lost romance while expressing gratitude.
James’s gentle vocals and emotional lyrics harmonize beautifully, resonating deeply with listeners.
Loved by many fans as a follow-up to his 2017 album “Feel Something,” this track is perfect for those trying to move forward despite heartbreak or for anyone who wants to cherish precious memories.
Queen Of DenmarkJohn Grant
It’s a song performed solo by John Grant.
The very minor-key, striking piano intro immediately draws you in.
The steady tempo and quiet delivery have a way of touching the heart.
It’s a ballad you can listen to at a relaxed pace.
Fingers CrossedLauren Spencer Smith
The song that captured global attention in 2022 is a poignant ballad by Canadian artist Lauren Spencer Smith.
It spread rapidly on TikTok and sparked a huge response worldwide, topping the charts in countries like Ireland and Norway.
The track portrays the pain of a betrayed love.
The expression “crossing fingers” is especially striking, symbolizing the hollowness of love’s promises.
Spencer Smith’s soaring vocals beautifully convey the frustration and heartache of a breakup.
The song is included on her debut album, Mirror, released in July 2023, and it resonates deeply with anyone who has endured the bitter side of love.
Breaking PointLogan Michael
The music of American singer-songwriter Logan Michael has the power to leave a deep mark on listeners’ hearts.
Released in October 2023, this work captures the moment of a breakup swirling with intense anger and disappointment.
We catch a glimpse of the protagonist’s torment as he spends sleepless nights with whiskey, and his resolve to throw everything away pierces the chest.
Transcending the bounds of pop/rock, this song will resonate especially with those who have decided to part ways with strong conviction.
Try listening to it in whatever setting makes you feel most at ease—whether in your bedroom or on a drive.
Don’t Forget MeMaggie Rogers
The song released in February 2024 reveals a new side of American singer-songwriter Maggie Rogers.
Set to a sound that skillfully blends folk and pop, the lyrics vividly capture the joy and unease she feels through a friend’s wedding, as well as her own views on love.
The line “Love me, but when it’s time to go, don’t forget me” conveys complex emotions that are sure to resonate with many listeners.
It’s a track that makes you want to blast it in the car, evoking the start of a new season.
Especially recommended for those standing at a turning point in life.
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.