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! Heart-wrenching Western songs—from timeless classics to the latest hits—(21–30)
HurtChristina Aguilera
This song makes you realize that it’s not easy to get back what you’ve lost.
What really mattered, what truly made you happy.
It conveys that unbearable, irreparable feeling of having hurt someone, and Christina’s powerful vocals resonate deep in your chest.
The One That Got AwayKaty Perry
When it comes to Katy, I think she usually has a lot of positive, up-tempo songs, but this one is a heart-breaking track and feels unusual.
The tempo is definitely Katy-like and upbeat, but the song’s theme is about a widow.
Listening to it together with the music video makes it even more poignant.
Tearjerkers! Heartbreaking Songs in Western Music — From Timeless Classics to the Newest Hits — (31–40)
If I die youngThe Band Perry
It begins with the opening line, “If I were to die young…” When I first heard it, I was surprised that a song like this existed.
It has a relaxed, upbeat country feel, but the lyrics—the heart of the song—reflect on life and on life and death.
In Your FeelingsMariah Carey
Featured on the album “Here for It All,” released in September 2025, this track is an R&B number that delicately weaves shifting emotions.
Co-produced with Anderson .Paak, it achieves a soundscape where the warmth of the drums melds with the luster of the strings.
It sings of an inner journey—from moments of heart-flutter and loss to gradually reclaiming confidence in oneself.
Mariah’s signature delicate melisma and richly resonant lower register lend profound conviction to every word.
It’s a song that gently stays by the side of anyone feeling swept away by their emotions.
Wrong DirectionHailee Steinfeld
Hailee Steinfeld, who shot to fame as a prodigy child actress after winning numerous awards for her role as the young girl in the 2010 film True Grit, directed by the Coen Brothers with Steven Spielberg as executive producer, is rapidly gaining popularity in Japan as a rising young actress—and she also has a career as a singer.
Her song Wrong Direction was released in January 2020, and Hailee herself is credited as one of the songwriters.
With lyrics that lay bare piercing emotions, a melody that swells from a whispering intro into something deeply emotional, and an arrangement that seems to echo those feelings, it’s a beautifully melancholic ballad that clearly showcases her skills as a singer-songwriter.
It’s said to be about her breakup with Niall Horan, and if that’s the case, the word “Direction” in the title feels particularly loaded with meaning.
Big girls don’t cryFergie
This is a solo song by Fergie from the Black Eyed Peas.
It might be her first breakup song since she started her solo career.
Fergie herself aims to be a strong woman and is quite disciplined, so I feel this song reflects the strength of not crying even after a heartbreak.
Say SomethingA Great Big World ft. Christina Aguilera
It’s a song featured in the film “If I Stay.” It’s unbearably heart-wrenching, and just listening to it makes me feel like I’m about to burst into tears.
A Great Big World came to Japan in 2015, and at that time they collaborated with May J.
on this song.