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)
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.
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.
Angels CryMariah Carey
A gem-like R&B ballad imbued with a heartfelt desire to mend a relationship on the brink of breaking.
Featured on the 2009 album “Memoirs of an Imperfect Angel,” a duet version with singer-songwriter Ne-Yo was released in January 2010.
Riding on luminous strings and resonant piano, Mariah Carey’s vocals are showcased to the fullest.
The longing to restore a bond with a loved one is woven through delicate harmonies, evoking a beauty like an angel shedding tears.
It’s a song to listen to when you feel uncertain about your relationship, or when you want to reflect on the bond you share with someone you love.
When your goneAvril Lavigne
It’s said to be one of Avril’s breakup songs, but depending on how you interpret it, it can also be taken as a song about losing someone important to you.
Even after that precious person is no longer right in front of you, the song powerfully expresses the enduring feelings you have for them, and Avril’s strong vocals resonate deeply in the chest.
Anywhere I Lay My HeadTom Waits
A song depicting a man who longs for the joyful days he sees others enjoying.
It is sung by Tom Waits, an American singer-songwriter and actor.
The song is also known for being recorded by actress Scarlett Johansson as the title track of her 2008 album.
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.
Adore YouHarry Styles
Harry Styles, a member of One Direction who also enjoys worldwide popularity as a solo artist.
This track, included on his December 2019 album Fine Line, perfectly blends a ’70s-style groove with a contemporary pop sensibility.
The lyrics, which express deep love and devotion for another, gently stay close to a lonely heart and wrap it in warmth.
The song has been widely embraced in many contexts, including its inclusion in the game Just Dance 2021.
The music video—like a film set on a fictional island—is also a must-see.
Give it a listen on nights when you want someone to affirm you, or when you’d like to quietly let your emotions out and have a good cry.