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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!

Tearjerkers! Heart-wrenching Western Songs — From Timeless Classics to the Newest Hits — (101–110)

When I Get ThereP!nk

P!NK – When I Get There (Lyric Video)
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.

Nice Knowing YouSadie Jean

Sadie Jean – Nice Knowing You (Lyric Video)
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.

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.

Have You EverBrandy

Brandy – Have You Ever (Official Video)
Have You EverBrandy

The song with which Brandy earned her first No.

1 on the Billboard Hot 100.

It was written by Diane Warren and produced by David Foster.

In 2007, it was covered by the Irish boy band Westlife on their album Back Home.

The Voice WithinChristina Aguilera

Christina Aguilera – The Voice Within (Official HD Video)
The Voice WithinChristina Aguilera

Even just the pure, incredibly clear and beautiful singing voice alone makes this song moving.

On top of that, the gentle, wistful melody turns it into a ballad.

With its powerful vocals, it feels like it gives you a push forward as you listen.