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 (41–50)
Best Thing I Never HadBeyoncé

I don’t think a Japanese person could write this song.
It sounds like they’re thanking the person they broke up with, but they’re not at all—they’re casually throwing in words of resentment.
And yet there’s nothing messy about it, and in the end they thank God.
I think it’s interesting and a good song.
Classic Western songs about regret. Recommended popular tracks (51–60)
Sorry Seems To Be The Hardest WordBlue

They are a British dance-vocal group.
They have a mature coolness and are great singers—perhaps similar to EXILE in Japan.
It’s a song about not being able to say words of apology, no matter what.
The emotions are poured into the vocals, and listening to it can bring you to tears.
Sorry Seems To Be The Hardest WorldBlue Featuring Elton John

The original is by Elton John, and the Japanese title is “Ballad of Sorrow.” Blue’s cover version was released in 2002.
It’s a beautifully melancholic broken-heart ballad that really touches the heart.
The music video where the original creator, Elton, and Blue sing the song together is simple and elegant.
Hard To Say I’m SorryCHICAGO

Some of you may have heard a cover version by a Japanese artist.
It’s a song by Chicago, the popular band from the United States.
It was released in 1982.
As the title suggests, the lyrics express the regret of not being able to be honest with someone you love.
Careless WhisperGeorge Michael

These are lyrics about someone who cheated but doesn’t want to give up on his girlfriend.
In romantic relationships, it’s common that even if the one who cheated regrets it, the person who was betrayed finds it very hard to forgive.
The content of the lyrics is unfortunate, but the song itself is wonderful.
The One That Got AwayKaty Perry

Rather than a heartbreak song, it’s closer to a memory song—or even a regret song.
The lyrics capture a very teenage vibe, about cutting loose and doing reckless things.
It’s poppy and easy to listen to, with an addictive hook that makes you want to sing it at karaoke.
The music video, which builds to a shocking ending, is a must-see.
GoodbyeNight Ranger

Night Ranger is a hard rock band from the United States.
This song was included on their 1985 album “7 Wishes” and became a hit, reaching No.
17 on the U.S.
charts.
It’s a wistful ballad.
The feelings of the man who “couldn’t say goodbye properly” are heartbreaking.


