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 — (1–10)
Don’t Look Back In AngerOasis
Released in 1995 by Oasis—the most powerful rock band to come out of the UK in the ’90s—Don’t Look Back in Anger is a timeless classic that has become a national anthem in their home country.
Sung by guitarist and songwriter Noel Gallagher, the song needs no explanation for anyone who has ever seen Oasis live; the overwhelming sense of unity as the entire crowd sings along is an unforgettable experience.
More recently, many will remember Ariana Grande and Coldplay’s Chris Martin performing the song at a charity concert following the tragic events in Manchester.
It’s best listened to not as a sad, mournful tune, but as a song to help you look forward after you’ve had a good, cathartic cry.
Good DaysSZA
It’s a song where wistfulness and hope coexist.
SZA, an American artist, delicately portrays the resolve to face forward while confronting past pain.
Her emotional vocals and dreamlike sound seep into the listener’s heart.
Released in December 2020, the track resonated with many and reached No.
9 on the Billboard Hot 100.
It’s recommended for times when you want to reflect on yourself or sort through your feelings.
As you listen to SZA’s voice, won’t you believe in “Good Days,” too?
So SickNe-Yo
An early classic released in 2006 by the hugely popular singer-songwriter Ne-Yo.
Even before debuting as a solo artist, he was highly regarded for his solid songwriting skills—famously credited as a composer of Mario’s 2004 smash hit “Let Me Love You.” One of Ne-Yo’s signature tracks, “So Sick,” is a gem of a mid-tempo ballad: a beautiful melody rooted in R&B but highlighted by smooth, universally appealing choruses, with the distinctive harp-like tone leaving a strong impression.
The lyrics capture a complex, aching state of mind—he’s “so sick of love songs” and yet can’t bring himself to turn off the radio—making it a truly first-rate heartbreaker.
Tearjerkers! Heartbreaking Western Songs — From Timeless Classics to the Newest Hits — (11–20)
You asked for thisHalsey
This song vividly captures a poignant sense of longing.
The lyrics, woven from the personal experiences of American singer-songwriter Halsey, lay bare the turmoil of a heart caught between societal expectations and self-actualization.
Featured on the album If I Can’t Have Love, I Want Power, released in August 2021, the track is marked by a heavy sound that incorporates industrial elements.
Combined with its dark, powerful musicality, it leaves a deep impression on listeners.
For those searching for their true selves or feeling on the verge of losing their identity within society, it offers empathy and courage.
Be AlrightDean Lewis
Dean Lewis is a singer-songwriter from Sydney whose debut album, A Place We Knew, released in 2019, reached No.
1 in his home country of Australia and earned worldwide acclaim.
Though he made a late-blooming debut in his thirties, he has become a standout singer-songwriter drawing attention here in Japan as well.
One of his signature songs, Be Alright, released in 2018, showcases his wonderful vocals and strong melodies, racking up over 500 million streams.
Its lyrics—about friends gently encouraging a protagonist who can’t get over a heartbreak—are deeply moving.
If you’re going through something similar, listen to your friends’ advice, put this song on, and keep looking forward, believing you can get through it.
I Want It That WayBackstreet Boys
Speaking of the Backstreet Boys, they’re a male group that epitomized the 1990s and, as the best‑selling boy band, have maintained enduring popularity well into the 2000s and beyond.
Among the many timeless hits they produced, this time I’ll introduce one of their signature songs, “I Want It That Way,” released in 1999 and a massive hit.
Back then, it was playing everywhere in Japan, too, and just hearing that ultra-famous chorus phrase will probably make many people think, “Oh, that song.” Even if you don’t understand the lyrics, the delicate melody alone gives you a twinge of sadness.
In fact, the lyrics poignantly depict a subtle “disconnect” between two important people, and when you realize their paths likely won’t cross, it leaves you with a profound sense of helplessness.
Lose You to Love MeSelena Gomez
It’s a beautiful ballad that captivates you from the moment you hear the solemn piano accompaniment and whisper-like vocals in the opening.
Released in 2019 by the popular singer and actress Selena Gomez, the single “Lose You To Love Me” topped the U.S.
Billboard chart, marking her first-ever No.
1 hit in the United States.
The raw emotion Selena pours into lyrics like “I had to lose you to love me” reaches its peak in the chorus, where majestic harmonies layer together.
Precisely because the melody and arrangement are restrained throughout, the song conveys not just sorrow, but a quiet strength as well.