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 (51–60)
Let Her GoPassenger

After we broke up and I lost them, I realized how I felt about that person and how important they were to me, and I regretted it deeply.
It’s a song filled with so much sadness and remorse that the tears start to flow naturally.
I think many people can relate to this song.
In Your LetterREO Speed Wagon

A single released by REO Speedwagon in 1981.
The song is in a major key and has a breezy pop feel, so it’s easy to assume it’s about something fun, but it’s actually a perfect breakup song.
It cheerfully sings, like, “Ah, I got dumped.”
What Hurts The MostRascal Flatts

The track was originally released by Mark Wills in 2003.
The version by the American country music band Rascal Flatts was released in 2006 and reached No.
1 on the U.S.
charts.
It’s a sad track that sings about the importance of not holding back your feelings and expressing them.
I Remember YouSkid Row

A rock ballad about the end of a relationship.
It was released in 1989 by the American heavy metal band Skid Row and reached No.
2 on the New Zealand charts.
It has been covered by artists such as DJ Deckstream and The Ataris.
Classic Western songs about regret. Recommended popular tracks (61–70)
Give You HellThe All-American Rejects

This song isn’t just about heartbreak; it’s a track that wishes anyone who’s had something awful happen—or anyone who gets upset every time they see a certain person—could make them feel the same way.
If you went through the worst kind of breakup, blasting this song and singing along at the top of your lungs might be the best way to blow off steam.
Gives You HellThe All-American Rejects

The All-American Rejects are an American band that’s hugely popular—especially in the United States, where two of their albums have been certified platinum.
They’re known for many songs that evoke a sense of youth and feature highly relatable lyrics, and this track, too, hits close to home as if it were about one’s own life.
You Won’t See MeThe Beatles

It’s been only a few days since I realized I no longer see myself reflected in your eyes, yet it feels as if years have passed…
The protagonist of this song is in the midst of heartbreak so intense that tears well up in their eyes.
A track from the 1965 masterpiece album Rubber Soul.


