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! Heart-wrenching Western Songs — From Timeless Classics to the Newest Hits — (121–130)
This Is The Sound OfSnow Patrol
A rock band that Scotland is proud of, Snow Patrol have released their first single in seven years.
Interweaving poetic, emotional lyrics with their signature melodic sound, the track is said to center on a long-distance relationship and truly resonates with listeners.
Speaking of the band, “Chasing Cars” from their 2005 album Eyes Open is known as the most-played song on UK radio in the 21st century.
With its romantic atmosphere, this new song is perfect for moments when you want to reminisce about a lover or think of someone special.
Why not give it a listen on a calm, quiet night?
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.
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.
WILDFLOWERBillie Eilish
This song by American artist Billie Eilish portrays the guilt of a protagonist who, while trying to comfort a friend after a breakup, ends up getting involved with that friend’s ex.
With delicate vocals and a soothing beat, the track blends elements of soft rock and pop to create a sound that resonates deeply with listeners.
Featured on the May 2024 album HIT ME HARD AND SOFT, it stands out for lyrics that express complex emotions with striking simplicity.
It was also performed on Saturday Night Live in October of the same year, capturing the hearts of many.
Highly recommended for anyone who has experienced heartbreak or complicated relationships, as it’s sure to evoke empathy.
Tearjerkers! Heartbreaking Songs in Western Music — From Timeless Classics to the Newest Hits — (131–140)
Empty BenchDavid Kushner
A Christmas song filled with a profound sense of loss and aching longing has arrived from American singer-songwriter David Kushner.
After his breakout smash hit “Miserable Man,” his new track conveys the deep sorrow of losing a loved one through the symbolic image of an empty bench.
Teaming up with producer Rick Nowels, the song blends a bittersweet, melancholic atmosphere with Kushner’s deeply emotive vocals.
The music video, released in December 2024, racked up hundreds of thousands of views within days, capturing the hearts of many.
It’s a work that gently stands by those who find themselves alone during a season made for thinking of someone special.
Tears can be so softChristine&the Queens
Héloïse Letissier, a singer who represents France.
Under her solo project name, Christine and the Queens, she released Tears can be so soft.
It explores themes of loneliness and sorrow, with lyrics that portray a yearning to see one’s family.
As you listen, pay attention to the eerie yet wistful sound built on string instruments.
By the way, the stylish music video was filmed in Los Angeles.
When I Get ThereP!nk
P!nk is one of America’s leading female R&B singers.
Her deep vocals with a husky edge always move people’s hearts.
Among her songs, the one I especially recommend is When I Get There.
As you can tell from the music video, it’s a song about her feelings for her late father, and it’s been crafted into an emotional track, reminiscent of the intensity we heard in Anywhere Away From Here with Rag’n’Bone Man.
