Classic Western songs about regret. Recommended popular tracks.
Here’s a list of classic Western songs about “regret.”
The genres vary—love, friendship, and regrets about the past.
As is often the case with Western music, the lyrics in each track feel disarmingly straightforward, almost awkwardly sincere.
There are some lesser-known hidden gems too, so don’t miss them.
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Classic Western songs about regret: Recommended popular tracks (71–80)
Could’ve BeenTiffany
This song is a love ballad that tenderly conveys feelings of regret.
I felt that many people could relate to the thought, “If only I had done things differently back then, could the two of us still be together as lovers?” No matter what kind of relationship you have, there are times when you go on living with regret.
It’s a song that really makes you think.
WreckedImagine Dragons
Imagine Dragons’ masterpiece “Wrecked.” If you’re in the mood to wallow in sadness, this song is for you.
At first glance it seems like a simple breakup song, but it carries a pervasive darkness beneath the surface.
The lyrics, which depict a man who, after parting with the one he loves, gradually turns into someone he hates, really cut deep.
The melody also matches that mood with a darker tone, so if you want to sink even further into your feelings after a breakup, be sure to give it a listen.
Caroline, NoThe Beach Boys
A ballad about a woman living a miserable life and wondering where she went wrong.
It was released by The Beach Boys in 1966 and was selected by Rolling Stone for “The 500 Greatest Songs of All Time.”
Love HurtsNazareth
Originally recorded by The Everly Brothers in 1960, the track sings about heartbreak and despair brought on by a passionate young romance.
The version by the Scottish hard rock band Nazareth was released in 1974 and reached the Top 10 on charts around the world.
EverytimeBritney Spears
A song by Britney Spears released in 2003, it’s an apology to a partner she ended up breaking up with because of her own actions.
She sings heartbreakingly about wanting them to come back.
With a slow melody and simple English, it should be easy to sing.
It’s a piece you’ll want to perform gently and emotionally.
Too Little Too LateJoJo
A breakup song by American pop singer JoJo.
It’s a bittersweet yet empowering track about deciding to break up for your own sake, even though the feelings are still there.
The title “A Little Too Late” feels somehow poignant, doesn’t it? Her powerful vocals make this a truly captivating piece.
Sorry Seems To Be The Hardest WordBlue ft. Elton John
A song by the British four-piece R&B group Blue that covers an Elton John track and even features a collaboration.
Its wistful melody, the sound of the piano, and the lyric “The words ‘I’m sorry’ are the most painful words” make it a very heartrending breakup song.