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!
- [2025] Moving Western songs that touch the heart: A roundup of recommended masterpieces
- Ranking of Tear-Jerking Western Songs [2025]
- 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.
- Top Cry-Inducing Western Songs Ranking [2025]
- Beautiful, lovely Western music. A roundup of recommended classic songs.
- Ranking of Melancholic Western Songs [2025]
- 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! Bittersweet Western Songs — From Timeless Classics to the Newest Hits — (151–160)
Casimir Pulaski DaySufjan Stevens
A song included on the 2005 concept album Illinois.
The title, Casimir Pulaski Day, refers to an Illinois state holiday held on the first Monday of March each year, honoring Casimir Pulaski, a Polish cavalry officer who fought in the American Revolutionary War.
White HorseTaylor Swift
This is a song by a woman who was cheated on and had her heart broken.
Even so, it expresses the desire to find someone better and keep moving forward.
Since Taylor has been heading in a more pop direction lately, I think it’s also nice that this song has a now-rare country style.
If I Were To DieWinona Oak
The song released in February 2024 by Swedish artist Winona Oak is a poignant love ballad that portrays the fear of losing someone you love and the courage to choose love anyway.
Winona’s clear, airy vocals delicately capture the vulnerability and beauty of falling in love.
This track was unveiled as a single ahead of the EP “Void,” scheduled for release on May 3, 2024.
Reflecting a difficult period Winona experienced, the piece is sure to resonate deeply with listeners.
It’s a recommended listen for anyone who, while imagining a possible farewell to a loved one, still cherishes the precious time spent together.
Little BonnieDrive-By Truckers
A country-gothic ballad written by lead singer and guitarist Patterson Hood about his first cousin, Bonnie, who died before he was born.
It sings of the family’s emotions and the fact that, even though she is gone, she remains an eternal presence in their hearts.
Cry Me A RiverJustin Timberlake
A song Justin Timberlake wrote about Britney Spears.
They both appeared on The Mickey Mouse Club and lived together for two and a half years before breaking up in 2002.
The piano on the track is performed by Scott Storch.
Damn You For Breaking My HeartCaitlyn Smith
If you love grand, sweeping songs, I recommend “Damn You For Breaking My Heart.” The verses are relatively calm, but once the chorus hits, it bursts into a powerful, fast-paced, expansive melody.
The lyrics are quite dark and heavy, so have a handkerchief ready when you look them up.
.
.
Tearjerkers! Heartbreaking Western Songs — From Timeless Classics to the Latest Hits — (161–170)
You should be sadHalsey
Halsey’s go-to tearjerker, “You should be sad.” The melody is generally on the brighter side, but the overall tone is serious.
Even if you don’t understand the lyrics, it’s the kind of song that can make you cry just from the melody.
The chorus has a powerful, scream-like feel that’s bound to stir your emotions.