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 Latest Hits — (61–70)
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.
Missing YouBackstreet Boys
The Backstreet Boys are a U.S.-born vocal group that dominated the music scene in the ’90s, and they’re also known for their 1999 album Millennium, which sold over 24 million copies worldwide.
This song is a hidden gem of a ballad quietly included on their classic 1997 release Backstreet’s Back, during the height of their fame.
The earnest longing to see a cherished person who has gone away is sung straight from the heart over a wistful melody.
The structure, with members taking turns as lead vocalists, and the beautiful harmonies woven by all five members are truly moving—simply mesmerizing.
It’s the kind of song that will gently comfort your heart when you want to bask in a bit of sentimentality at night or when an old love suddenly comes to mind.
I Don’t Like YouGrace VanderWaal
I recommend this song, “I Don’t Like You,” to anyone struggling with relationship issues.
Love can sometimes force you to endure things.
“I Don’t Like You” conveys the pain of a woman who can’t bring herself to tell her partner that she doesn’t really like them.
I’m not the only oneSam Smith
“I’m not the only one” means “I’m not the only one,” but when I first heard the song, I thought it was about a man being cheated on by a woman.
After watching the music video, though, I realized it’s a story about a woman being cheated on by a man.
Sam Smith’s warm yet heartrending voice brings me to tears.
We Are the WorldUSA For Africa
Rather than a tearjerker, it’s a song that genuinely moves you.
It’s the globally renowned classic born in 1985 from “USA for Africa,” a project proposed by Harry Belafonte inspired by the UK’s Band Aid to relieve famine in Africa.
As a charity single created to help alleviate the worsening famine in Africa, it brought together 45 of the era’s top American superstars, leaving its mark on history as a landmark undertaking.
There’s no need to rehash the significance or brilliance of the song itself, but collaborations of this caliber among such extraordinary vocalists are exceedingly rare, and as a music fan, the mere fact that this track came to be is deeply moving.
Be sure to check out the documentary footage of the recording sessions as well!
Bleeding LoveLeona Lewis
It’s a song that really brings out Leona Lewis’s sexy, powerful vocals.
The melody has a somewhat rhythmic, pop-like structure, and it’s a bittersweet track that sings about the joy that comes from falling in love.
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.