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 — (101–110)
OutsideCalvin Harris ft. Ellie Goulding
Outside is a song by DJ Calvin Harris, so the track itself is a very upbeat club tune.
But the key theme is about the struggle with emotional distance in a relationship (at least that’s how I interpret it).
Someone who’s close yet feels far away—I really feel that sense of melancholy.
TornNatalie Imbruglia
A song written by songwriters Anne Preven and Scott Cutler with producer Phil Thornalley.
It was originally recorded by Danish singer Lis Sørensen under the title “Brændt.” This version by Australian actress Natalie Imbruglia is included on her debut album “Left of the Middle,” released in 1998.
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.
Nice Knowing YouSadie Jean
This is an expressive song that skillfully weaves together the bittersweetness and forward-looking emotions characteristic of Sadie Jean’s music.
True to her American roots, the lyrics brim with unfiltered, genuine feelings and leave a strong impression.
While conveying the loneliness of a breakup, the song also wishes happiness for the other person, capturing a complex emotional state in a clear, translucent vocal delivery.
Included on her debut EP, “Simple Like 17,” released in December 2023, the track strongly reflects Sadie Jean’s personal experiences and emotions.
The delicate words she crafted while attending New York University make this a song that truly resonates with anyone who has just gone through heartbreak.
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.
Tearjerkers! Heart-wrenching Western songs—from timeless classics to the latest hits—(111–120)
What it takesAerosmith
This song conveys an overwhelming feeling of having let go of the woman he loves.
The breakup wasn’t what he wanted, and he’s willing to do anything to win her back.
That’s why he’s asking to be told what he needs to do.
Steven’s husky voice really resonates, and the melody in the chorus is absolutely irresistible.
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.