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)

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.

Raise the rankinglower

Report a problem

Empty BenchDavid Kushner

David Kushner – Empty Bench (Official Music Video)

Empty BenchDavid Kushner

A Christmas song filled with a profound sense of loss and aching longing has arrived from American singer-songwriter David Kushner.

After his breakout smash hit “Miserable Man,” his new track conveys the deep sorrow of losing a loved one through the symbolic image of an empty bench.

Teaming up with producer Rick Nowels, the song blends a bittersweet, melancholic atmosphere with Kushner’s deeply emotive vocals.

The music video, released in December 2024, racked up hundreds of thousands of views within days, capturing the hearts of many.

It’s a work that gently stands by those who find themselves alone during a season made for thinking of someone special.

Raise the rankinglower

Report a problem

Last NightMorgan Wallen

Morgan Wallen – Last Night (One Record At A Time Sessions)

Last NightMorgan Wallen

“Last Night” is a love song by Morgan Wallen, notable for its gentle vibe.

He achieved the rare feat for country music of debuting at No.

1 on the U.S.

albums chart with Dangerous: The Double Album.

In “Last Night,” the line “There’s no way that was the last night” leaves a strong impression, and the aching lyrics about not being able to let go of someone special tighten the chest.

If you’re going through a painful relationship, I hope listening to this song helps you get through it.

Raise the rankinglower

Report a problem

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.

Raise the rankinglower

Report a problem

You should be sadHalsey

Halsey – You should be sad

You should be sadHalsey

Halsey’s go-to tearjerker, “You should be sad.” The melody is generally on the brighter side, but the overall tone is serious.

Even if you don’t understand the lyrics, it’s the kind of song that can make you cry just from the melody.

The chorus has a powerful, scream-like feel that’s bound to stir your emotions.

Raise the rankinglower

Report a problem