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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Tear-Jerking! Heartbreaking Songs in Western Music — From Timeless Classics to the Newest Hits — (91–100)
I’ll Be Over YouTOTO
This is a song that drew a lot of attention as a ballad by a band famous for rock.
With its slow tempo and gentle mood far removed from rock, the melody makes it a very calming listen.
The music video, set against a sunset backdrop, also matches the impression of the song.
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.
Tearjerkers! Heart-wrenching Western Songs — From Timeless Classics to the Newest Hits — (101–110)
I don’t want you backEamon
It’s a bittersweet song, but it’s also packed with a lot of anger toward the ex-girlfriend.
Since the lyrics are full of F**k, they made quite a few changes when it aired on TV.
Still, I think it’s great how it expresses honest feelings about love so directly.
Wake Me Up When September EndsGreen Day
This is a song about a country boy who becomes an American volunteer soldier.
Also, the title means “Wake me up when September ends,” which indirectly alludes to the 9/11 attacks and strongly expresses an anti-war stance.
PerfectSimple Plan
It’s a song that expresses the complicated feelings of adolescence—knowing I’m not perfect and feeling sorry toward my parents.
I think the reason Simple Plan resonates so well with teenagers is that they directly capture these uniquely adolescent emotions in their music.
I discovered this song when I was in middle school and listened to it all the time.
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.
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.