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 — (81–90)
Through the RainMariah Carey
It’s a song by a diva known for singing many ballads.
Her voice is husky yet somehow clear and soaring, making it a truly pleasant listen.
If you focus on the lyrics, which are steeped entirely in a ballad mood, the song becomes even more heartrending.
California King BedRihanna
It’s a mellow ballad by Rihanna, an artist renowned for working across a wide range of genres like R&B and soul.
Her powerful, clear vocals match the melody perfectly, making it a song that truly resonates with the heart.
Eternal FlameThe Bangles
It seems it was released in Japan under the title “A Full Heart of Love.” The Bangles are a four-woman girls’ band, and their gentle, feminine melodies are really wonderful.
Pay attention to the cute singing voice of the vocalist, Susanna Hoffs.
Depression (feat. Coconut Records)Ben Kweller
Have you ever experienced the kind of despair that feels like all the color has drained from the world after suddenly losing a beloved family member? “Depression” by American singer-songwriter Ben Kweller is a song that lays bare his feelings for his son, who died in a car accident.
The fact that he wrote it while listening to recordings his son left behind conveys, almost painfully, the heart-rending ache and deep love he feels as a father.
His voice, singing without hiding his despair, is sure to offer comfort to those carrying similar pain.
This song, which strives to find light from the depths of sorrow, may give you the strength to move forward.
It’s So Hard to Say Goodbye to YesterdayBoyz II Men
After parting with someone dear, have you ever felt your chest tighten with the thought that you can never return to the joyful “yesterday”? The song “It’s So Hard to Say Goodbye to Yesterday” by the American R&B group Boyz II Men is a classic that sings of longing for the past and the pain of farewell.
Precisely because it’s performed a cappella, without any instruments, the warmth and poignancy of their voices seep directly into the heart.
It’s as if the beautiful harmonies gently embrace the sorrow that overflows no matter how hard you try to hold it back.
This song feels like a warm presence that quietly stays close to a heart that has experienced a painful parting, allowing the tears to flow.
The Wind Cries MaryThe Jimi Hendrix Experience
A song that Jimi Hendrix was inspired to write by his then-girlfriend, Kathy Mary Etchingham.
They argued about her cooking, and in anger she started throwing pots and pans, then eventually left to spend the night at a friend’s place.
There’s a story that when she came back, Jimi had written The Wind Cries Mary for her.
Tear-Jerking! Heartbreaking Songs in Western Music — From Timeless Classics to the Newest Hits — (91–100)
Don’t Cry, Put Your Head On My ShoulderTom Odell
The new song released in May 2025 by British singer-songwriter Tom Odell is a truly exquisite ballad that resonates deep within the heart.
Its delicate, piano-centered arrangement is layered with his warm vocals, and the lyrics—centering on gentle comfort for those in sorrow—are profoundly moving.
Carefully crafted over a nine-month production period, the piece is positioned as the second single from the album “A Wonderful Life.” The music video, featuring his wife Georgie, has also drawn attention.
It’s the kind of track you’ll want to listen to alone on a quiet night—a masterpiece especially recommended for those facing life’s hardships or seeking emotional support.