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)
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.
You Break Me FirstTate McRae
This is a heartbreak song by Canadian singer-songwriter Tate McRae that holds both strength and fragility.
It portrays the cold yet sorrowful feelings when an ex who once hurt you reaches out only when it’s convenient for them.
The line “You’re the one who broke me first” pushes them away, squeezing your chest as you hear it.
Behind those searing words, it feels as if there’s a deep sadness so intense that without saying them, her heart might fall apart.
For anyone who’s been through a painful love, it may resonate with that moment when you put on a brave face to protect yourself.
Her delicate vocals riding over a quiet beat gently wrap around that pain and bring you to tears.
Wish You The BestLewis Capaldi
Lewis Capaldi is a singer-songwriter from Scotland.
His 2018 single “Someone You Loved” drew attention for reaching No.
1 on the U.S.
singles chart—a rare achievement for a Scottish artist.
And his 2023 release “Wish You The Best” is a love song with a strikingly poignant chorus that says, “I don’t want to be away from you.” It’s an incredibly moving track that might just bring you to tears.
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.