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 — (41–50)
Pale Blue EyesVelvet Underground
A song included on the self-titled album released in 1969.
It was written by Lou Reed.
In contrast to their previously violent lyrics, it is a quiet, relaxed, lullaby-like sweet love song.
It has been covered by many artists, including Patti Smith and R.
E.
M.
Tearjerkers! Heart-wrenching Western songs — from timeless classics to the latest hits — (51–60)
SmileMorgan Wallen
American singer-songwriter Morgan Wallen’s new song is making waves.
Surprise-released in December 2024, the track is a poignant ballad that looks back on a past relationship.
Sparked by a smiling face in a photograph, the lyrics stir nostalgia for a love that’s been lost.
Wallen’s emotive vocals and a sound that blends country and pop are especially compelling.
Fans are also looking forward to its debut at his first-ever festival slated for 2025.
It’s a perfect song for when you’re in the mood to sink into old memories.
Whatcha sayJason Derulo
This is the song that became famous during the well-known Tiger Woods cheating scandal.
Jason Derulo is said to have composed the song himself while imagining Woods.
Jason also made his debut with this track.
At first, his dancing wasn’t very good, but now he moves like a professional dancer.
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.
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.
Not A Day Goes ByLonestar
The American country music band Lonestar released a single from I’m Already There in January 2002, a gem of a ballad that portrays profound sorrow and a sense of loss after losing a loved one.
Its gentle, resonant melody, rich harmonies, and deeply expressive vocals blend beautifully to convey both the pain of grief and the enduring love for someone dear.
The song touched many listeners, reaching No.
3 on the Billboard Hot Country Singles chart, and was nominated for Best Country Performance by a Duo or Group with Vocal at the 45th Annual Grammy Awards in 2003.
With its quietly consoling character, it has often been chosen to comfort those who have lost someone and for use in memorial settings—a heartwarming piece that offers solace.
When I Was Your ManBruno Mars
Bruno Mars continues to achieve overwhelming commercial success with his outstanding singer-songwriter talent.
Some people may still associate him only with upbeat party tunes because of the glamorous disco-funk image of his blockbuster third album, 24K Magic.
But listening to the song we’re featuring today, When I Was Your Man, will surely change that perception.
It’s a piano ballad from his second album, Unorthodox Jukebox, released in 2012, which was given the Japanese title “Kimi ga Ita Ano Koro ni” (Back to When You Were Here).
Bruno’s emotional vocals, expressing a complex mix of regret and lingering feelings for an ex, along with enduring love, will resonate deeply.
Why not entrust your tangled emotions to this song as you sit alone in a dark room?