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

I’m Not Gonna Miss YouGlen Campbell

Glen Campbell – I’m Not Gonna Miss You
I'm Not Gonna Miss YouGlen Campbell

Glen Campbell revealed in 2011 that he was battling Alzheimer’s disease.

This song is the last piece he wrote with Julian Raymond.

Inspired by his struggle with Alzheimer’s, it serves as a message to his wife and children.

No AirJordin Sparks ft. Chris Brown

Jordin Sparks, Chris Brown – No Air (Official Video) ft. Chris Brown
No AirJordin Sparks ft. Chris Brown

A song about a dying relationship produced by the R&B/pop producer duo The Underdogs, who are also known for their work on the Dreamgirls soundtrack.

It’s a duet by Jordin Sparks and her labelmate Chris Brown, and it spent seven weeks at No.

1 on the New Zealand singles chart.

Please Don’t Fall In Love With MeKhalid

Khalid – Please Don’t Fall In Love With Me (Visualizer)
Please Don't Fall In Love With MeKhalid

This song stands out for its poignant lyrics and a melody that really seeps into the heart.

Khalid, an American artist, weaves a story drawn from his own experiences, inviting listeners on a journey through love, loss, and self-discovery.

The arrangement, which samples an Alicia Keys classic, is excellent and reads as a thoughtful homage to R&B’s heritage.

Released in April 2024, the track signals the beginning of a new musical chapter for Khalid.

Anyone who’s been hurt by past relationships will likely relate.

It’s the perfect song for quiet nights alone or reflective rainy-day drives.

RainMadonna

Madonna – Rain (Official Video) [HD]
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

Michael Bolton – How Am I Supposed To Live Without You
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

Natalie Imbruglia – Torn (Official Video)
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

Post Malone – Circles (Official Music Video)
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.