Lovely Western music

Songs That Make You Cry: Heart-Wrenching Western Music—from Timeless Classics to the Newest Hits

Active club DJkento
Active club DJ. With over five years on the front lines of the club scene, they freely cross over from dance music to US hip-hop and Japanese rap. Blending in their own edits with assured mixing, they craft a unique groove that captivates the floor.
music writerKOH-1
Started working as a music writer as a side job while employed at a record shop, and for over 18 years I’ve contributed to music magazines, disc guide books, mooks, and web media. As a writer my main field is Western music, but as a listener for over 35 years, I always try to keep my curiosity alive with the motto “I like what I like.” I have experience playing in bands, where I was a bassist who handled songwriting and composition. Instruments I’ve played include bass, guitar, and piano. I began studying English in my mid-40s and continue to do so today.

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! Heartbreaking Western Songs — From Timeless Classics to the Latest Hits — (161–170)

White HorseTaylor Swift

Taylor Swift – White Horse

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.

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Little BonnieDrive-By Truckers

Little Bonnie

Little BonnieDrive-By Truckers

A country-gothic ballad written by lead singer and guitarist Patterson Hood about his first cousin, Bonnie, who died before he was born.

It sings of the family’s emotions and the fact that, even though she is gone, she remains an eternal presence in their hearts.

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WILDFLOWERBillie Eilish

Billie Eilish – WILDFLOWER (Official Lyric Video)

WILDFLOWERBillie Eilish

This song by American artist Billie Eilish portrays the guilt of a protagonist who, while trying to comfort a friend after a breakup, ends up getting involved with that friend’s ex.

With delicate vocals and a soothing beat, the track blends elements of soft rock and pop to create a sound that resonates deeply with listeners.

Featured on the May 2024 album HIT ME HARD AND SOFT, it stands out for lyrics that express complex emotions with striking simplicity.

It was also performed on Saturday Night Live in October of the same year, capturing the hearts of many.

Highly recommended for anyone who has experienced heartbreak or complicated relationships, as it’s sure to evoke empathy.

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You Are Not AloneMichael Jackson

Michael Jackson – You Are Not Alone (Official Video)

You Are Not AloneMichael Jackson

It’s a song that’s also famous for having reached number one on the Billboard chart.

I think many people in Japan have heard it on TV shows and the like.

Michael Jackson’s gentle vocals match beautifully with the mellow melody.

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Fall On MeA Great Big World, Christina Aguilera

Fall On Me

Fall On MeA Great Big World, Christina Aguilera

Fall On Me is a collaboration between Christina Aguilera and A Great Big World.

It showcases an emotional side of Christina, different from her usual, full-throttle R&B intensity.

Highly recommended for those who enjoy tear-jerking R&B.

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In conclusion

From timeless classics that have been loved for years to the latest tracks likely to become future standards, we’ve brought you a selection of tear-jerking, heart-wrenching songs. Did you discover a new favorite bittersweet song among the ones introduced in this article? When you feel sad or weighed down, let it all out and detox by having a good cry while listening to your favorite tunes!