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 Songs in Western Music — From Timeless Classics to the Newest Hits — (31–40)
Love Is a Losing GameAmy Winehouse
This is an achingly poignant masterpiece by Amy Winehouse, the singer from England.
True to its title, “Love Is a Losing Game,” it sings of the futility of a love you know will never be rewarded, no matter how hard you try.
Even after giving everything, you’re left behind in the end, with a crushing sense of defeat and helplessness.
Anyone who’s worn themselves down in a barren, one-sided love will feel the sting of this hopeless situation all too well.
Her voice—deep and tinged with resignation—doesn’t console so much as it quietly stays beside the pain.
It’s a song that seeps into your heart on nights when you’re burdened with sorrow that has nowhere to go.
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.
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.
BreakevenThe Script
A single released in 2008 by the Irish pop-rock band The Script.
It reached No.
10 on the Irish charts and No.
3 in Australia, and also hit No.
1 on Billboard’s Adult Pop chart.
Just Want You to KnowBackstreet Boys
This song by the American group Backstreet Boys pours unspoken feelings for a former lover into a powerful sound.
Released in July 2005, it’s included on the acclaimed album “Never Gone” and reached the top 10 on the charts in the UK and Spain.
Stepping beyond their traditional pop image, the track shifts to a rock-tinged sound marked by memorable guitar riffs, revealing a new side of the group.
It portrays a bittersweet yet straightforward male perspective, wishing to tell someone they’ll never meet again, “There’s just this one thing I want you to know.” If you have lingering feelings about a past relationship, listening to this song might help you face your emotions.
Tearjerkers! Heartbreaking Western Songs — From Timeless Classics to the Latest Hits — (41–50)
Because of youKelly Clarkson
A song Kelly Clarkson wrote about her parents’ divorce, which she experienced when she was six years old.
It depicts her resolve not to repeat her parents’ mistakes and her anxiety about falling in love for fear of experiencing the same pain they did.
She had written the song even before she won American Idol.
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.