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.
- Classic Western songs about getting back together: recommended popular tracks
- [Songs About Loving Yet Parting] Love songs for those who want to overcome heartbreak
- Western songs about saying “goodbye” — perfect for bereavement or a departed lover
- Beautiful, lovely Western music. A roundup of recommended classic songs.
- [Unrequited Love] Heart-wrenching Love Songs | A Roundup of Tear-Inducing Crush and Breakup Tracks
- [Trash Songs] A carefully curated selection of tracks about the lowest, worst kind of loser—and hidden gems!
- [2026] Moving Western songs that touch the heart: A roundup of recommended classics
- Breakup songs by Western bands. World-famous classics and popular tracks.
- [2026] Western music you've heard at least once — from trending new tracks to timeless classics
- [Adultery Song] A forbidden song about an affair that sings of an impossible love
- [TikTok] “I know this chorus!” A collection of popular Western songs on TikTok [2026]
- [Foreign-Love Songs] A roundup of popular overseas love songs and romance songs [2026]
- Western classic songs covered by Japanese artists. Hit songs rediscovered through Japanese-language covers.
Masterpieces of Western music about regret: Recommended popular songs (21–30)
Best I Ever HadGary Allan
Originally released in 2001 by Vertical Horizon under the title “Best I Ever Had (Grey Sky Morning).” The version by American country music singer Gary Allan was released in 2005 after his wife’s suicide.
Praying For TimeGeorge Michael
A melancholic track that sings about people suffering from poverty and inequality, as well as hypocrisy, hatred, and regret.
It was released in 1990 by British singer-songwriter George Michael.
The song became a hit around the world, reaching No.
1 on the charts in the United States and Canada.
BlurryPuddle of Mudd
This song gained attention in Japan when it was used as the theme for the shooting game “Ace Combat 5: The Unsung War.” It’s a track by the American rock band Puddle of Mudd, included on their 2001 album “Come Clean.” The lyrics express a poignant feeling of wondering how things ended up this way, despite how important it all was.
Running BackTHIN LIZZY
It’s a song by Thin Lizzy, the rock band from Ireland.
The laid-back rhythm makes it really pleasant to listen to.
It’s included on their 1976 album Jailbreak.
The lyrics compare a sad love affair to an American football game.
Don’t Look Back In AngerOasis
Oasis is a hugely popular band often called the second coming of the Beatles, and this particular song is so famous that many people recognize it even if they don’t know the title.
When you listen to the lyrics, the song takes on even more depth, so I recommend taking the time to focus on the words and enjoy it.
SorryCiara
A track that sings about the need to clear up misunderstandings.
It’s an R&B track released in 2012 by American singer-songwriter Ciara, and it became a hit in the United States, the United Kingdom, and other countries.
It was inspired by Ginuwine’s 2001 track “Differences.”
If I Could Turn Back TimeCher
A track produced by Diane Warren, who has also worked on songs for artists like Aretha Franklin and Celine Dion.
It sings about regret for every word and action that hurt a lover.
It was released in 1989 by Cher, the American singer and actress.