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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Tear-Jerking! Heartbreaking Songs in Western Music — From Timeless Classics to the Newest Hits — (91–100)
Don’t Cry, Put Your Head On My ShoulderTom Odell
The new song released in May 2025 by British singer-songwriter Tom Odell is a truly exquisite ballad that resonates deep within the heart.
Its delicate, piano-centered arrangement is layered with his warm vocals, and the lyrics—centering on gentle comfort for those in sorrow—are profoundly moving.
Carefully crafted over a nine-month production period, the piece is positioned as the second single from the album “A Wonderful Life.” The music video, featuring his wife Georgie, has also drawn attention.
It’s the kind of track you’ll want to listen to alone on a quiet night—a masterpiece especially recommended for those facing life’s hardships or seeking emotional support.
Yesterday Once MoreCarpenters
This classic song, which sings of love and nostalgia for music, is one of the Carpenters’ signature works, released in May 1973.
Created by the American brother-and-sister duo, it is imbued with deep affection and longing for pop songs of the 1950s and ’60s, beautifully balancing Karen Carpenter’s warm, tender vocals with Richard Carpenter’s delicate arrangements.
It reached No.
2 on the Billboard Hot 100 and became a worldwide hit.
It’s a must-listen for everyone who loves music—and for those moments when you want to look back on your youth.
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.
the way things gobeabadoobee
Beabadoobee is a British singer-songwriter.
While she excels at ’90s alternative rock and dream pop, “the way things go” is a ballad that portrays a heartbroken woman looking back on the past and letting her unresolved feelings build up.
Her high, airy vocals convey that bittersweet state of mind without holding anything back.
It’s also a song about long-distance love, so those who’ve experienced it may find it especially relatable.
I’m SorryAli Gatie
Ari Gatie, the Canadian artist known for his sweet voice, released a new song in January 2024 that’s been generating buzz.
Lyrically weaving themes of regret and reflection in love, the track is a beautiful three-and-a-half-minute piece that masterfully blends pop and R&B.
Born in 1997, Ari’s lyrics flow as if written in a single stroke, gently embracing listeners who’ve experienced heartbreak.
His signature style—renowned for vividly portraying emotion—shines in this work as well.
When you want your post-breakup feelings to be stirred, lend an ear to the melody and lyrics that will resonate deep within your heart.