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! Heartbreaking Western Songs — From Timeless Classics to the Newest Hits — (11–20)
FlowersMiley Cyrus
It’s a powerful song carrying a message of self-love and independence.
Released in January 2023 by American artist Miley Cyrus, the track drew attention as a pop song infused with disco and funk elements.
Its lyrics, which emphasize the importance of valuing oneself without relying on past relationships, have resonated with many listeners.
It also achieved major commercial success, including 13 consecutive weeks at No.
1 on the Billboard Hot 100.
Highly recommended for those who want to cherish time alone or boost their self-esteem.
Happier Than EverBillie Eilish
A song by American artist Billie Eilish that candidly chronicles her past romantic experiences.
It begins as a quiet ballad and shifts into a guitar-driven rock style, a structure that brilliantly mirrors the emotional changes after a breakup.
Released in July 2021, it is the title track of the album Happier Than Ever and centers on themes of her growth and independence.
Reflecting on her relationship with an ex, the lyrics trace how she learned the importance of valuing herself.
This work conveys the joy of overcoming painful experiences and discovering a new self, making it recommended for those looking to recover from the pain of heartbreak.
Someone You LovedLewis Capaldi
A poignant, heart-stirring ballad by Scottish artist Lewis Capaldi is capturing widespread attention.
Centered on themes of heartbreak and loss, the song is marked by deeply emotional lyrics and a powerful vocal performance.
Released in November 2018, it spent seven consecutive weeks at No.
1 on the UK Singles Chart and also reached No.
1 on the U.
S.
Billboard Hot 100.
The music video, produced in collaboration with an organ donation charity, tells a moving story.
It’s a song that stays close to your heart on solitary nights or whenever you’re remembering someone special.
Easy On MeAdele
The exquisite ballad woven by Adele, hailing from the UK, is a cry from the soul born out of the life-changing experience of divorce.
Carried by a gentle piano melody, her powerful voice resonates deeply.
Released in October 2021, the song garnered major attention as the lead single from the album “30.” Adele writes candidly from her own experience, imbued with love and apology to her son.
It’s a track I highly recommend to anyone standing at a crossroads in life or looking to sort out their feelings.
Why not savor it slowly in a bedroom or a quiet café?
drivers licenseOlivia Rodrigo
This poignant love song by American artist Olivia Rodrigo uses getting a driver’s license for the first time as its theme to depict the pain of heartbreak.
Released in January 2021, her debut single captivated many listeners with its piano-centered, beautiful melody and relatable lyrics.
Evoking the feeling of lonely nighttime drives after a breakup, this track is especially recommended for young people experiencing the end of a relationship and personal growth.
It spent eight consecutive weeks at No.
1 on the Billboard Hot 100 and won a Grammy, making it one of her signature works—be sure to give it a listen.
Your SongElton John
Just from the intro that begins with a lyrical piano tone, you know it’s an achingly beautiful masterpiece bursting with emotion! It’s one of the early signature songs by Elton John, a singer-songwriter who will go down in music history, and in Japan it’s also well known by the title “Boku no Uta wa Kimi no Uta” (My Song Is Your Song).
In 2019, the autobiographical musical film Rocketman was released, which, much like Queen’s resurgence, gave younger generations a chance to discover John anew.
Featured on the Rocketman soundtrack, Your Song was released in 1970; it’s a perfect love song that needs nothing added, blending a folky texture with elements of jazz.
The lyrics are simple and easy to understand, and perhaps it’s nice, from time to time, to immerse yourself in such a sweet and gentle world and spend a moment shedding warm tears that are different from sadness.
Tearjerkers! Heart-wrenching Western songs—from timeless classics to the latest hits—(21–30)
ImaginationShawn Mendes
Shawn Mendes, the Canadian singer-songwriter who’s won popularity with his sweet looks and catchy musical style.
This is a hidden gem included on the deluxe edition of his debut album, Handwritten, which drew attention when he was 16.
The song revolves around an achingly sad unrequited love: being unable to confess your feelings to the person you like and becoming their lover only in your imagination.
His crystalline vocals and the gentle tones of the acoustic guitar portray the protagonist’s pure, single-minded feelings, tightening your chest.
Released in April 2015, this emotional track is one you’ll want to hear if you’re holding onto a love you know will never come true.