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!
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Tearjerkers! Bittersweet Western Songs — From Timeless Classics to the Newest Hits — (151–160)
Crying My Eyes OutStephen Puth
For those who want to listen to a tear-jerker but aren’t into songs that feel too heavy, Crying My Eyes Out is highly recommended.
The lyrics are crafted to be sad, but the melody is an easy-to-listen-to, electro-infused pop sound.
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.