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! Heartbreaking Western Songs — From Timeless Classics to the Latest Hits — (41–50)
MapsMaroon 5
The music video for this song is quite provocative.
In it, a girl who witnesses her boyfriend cheating ends up dying in an accident, making for a very bitter aftertaste.
The song itself was written by the composers behind Payphone and Moves Like Jagger, so it’s very up-tempo.
Tearjerkers! Heart-wrenching Western songs — from timeless classics to the latest hits — (51–60)
In Your FeelingsMariah Carey
Featured on the album “Here for It All,” released in September 2025, this track is an R&B number that delicately weaves shifting emotions.
Co-produced with Anderson .Paak, it achieves a soundscape where the warmth of the drums melds with the luster of the strings.
It sings of an inner journey—from moments of heart-flutter and loss to gradually reclaiming confidence in oneself.
Mariah’s signature delicate melisma and richly resonant lower register lend profound conviction to every word.
It’s a song that gently stays by the side of anyone feeling swept away by their emotions.
I Don’t Like YouGrace VanderWaal
I recommend this song, “I Don’t Like You,” to anyone struggling with relationship issues.
Love can sometimes force you to endure things.
“I Don’t Like You” conveys the pain of a woman who can’t bring herself to tell her partner that she doesn’t really like them.
Tears In HeavenEric Clapton
Eric Clapton is a legendary singer-songwriter and guitarist whose name is etched in music history, continually creating timeless songs loved across generations.
“Tears in Heaven,” distinguished by its warm fingerpicked acoustic guitar and the mellow tone of a fretless acoustic bass, was released in 1992.
It became a hit as the theme song for the film Rush and is one of Clapton’s signature tracks, even earning a Grammy nomination.
The story behind the song is deeply sorrowful: Clapton wrote it in 1991 as a tribute to his young son, who tragically passed away in an accident.
With that in mind, reading the lyrics while listening to the song evokes the image of Clapton striving to overcome tragedy and move forward—something that is sure to bring listeners to tears.
Eyes ClosedEd Sheeran
The lead single from Ed Sheeran’s 2023 album “-” is “Eyes Closed,” which reached number one on the UK Singles Chart.
The song is dedicated to DJ Jamal Edwards, a close friend of Ed’s who passed away in 2022.
Its lyrics about “losing someone close to you” really hit home.
The blue monster that appears in the music video is said to symbolize Ed’s grief.
EverytimeBritney Spears
Britney has quite a few intense tracks, but this one is a relaxed ballad.
It’s also a heartbreak song that expresses the complex feelings of loving someone who won’t look your way.
I think it’s one of those songs that reaffirms that Britney really does have vocal prowess.
Lost In Your EyesDebbie Gibson
It seems that the artist singing this song, Debbie Gibson, was also active as an actress.
Her clear soprano voice matches the bright piano melody very well.
Apparently, she also plays the piano herself.