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! Bittersweet Songs in Western Music—from Timeless Classics to the Newest Hits—(141–150)
RainMadonna

It’s a song with a very distinctive and mysterious melody.
It has become one of Madonna’s signature ballads and is a classic that everyone knows.
In the music video, the renowned pianist Ryuichi Sakamoto even appears in the role of a director.
How Am I Supposed To Live Without YouMichael Bolton

This song, styled after 1960s–70s soul music and lamenting the loss of a lover, was written by Michael Bolton and Doug James.
It was originally offered to Air Supply, but because the executive producer wanted changes to the chorus and Bolton refused, it has been placed on indefinite hold.
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.
CirclesPost Malone

I think it’s hard to catch the lyrics of songs in English.
With this song, “Circles,” many people might feel it sounds bright if they just listen to the melody.
The vibe is upbeat, but in fact it’s a song about losing someone important.
Please give it a listen.
What Hurts The MostRascal Flatts

A song with the message “Don’t wait to tell someone how you feel; don’t hold back your feelings.” It was originally first recorded in 2003 by country singer Mark Willis.
This Rascal Flatts version reached No.
1 on the Country and Adult Contemporary charts in 2006.


