The feeling that always shows up late
Regret is the one emotion that only arrives after the door has closed. You cannot feel it in the moment, only afterward, when the wrong word is already said and the chance to say the right one is gone. Every song on this list lives in that afterward. Yesterday is Paul McCartney waking up to a love that vanished overnight. If I Could Turn Back Time packs the entire feeling into one impossible wish. The subject does not change much from decade to decade, because the mistake at the center of it is as old as people.
A few of these songs do the rare and useful thing of owning the fault outright. Back to December is Taylor Swift apologizing to someone she treated badly, naming her own mistake instead of the other person’s. The Living Years is a son listing everything he never told his father while there was still time to say it. These are harder to write than the ones that blame someone else, and they land harder too, because most real regret is about what we did rather than what was done to us.
Grief, guilt, and the grocery store
Regret shades easily into grief, and the list keeps the overlap. Tears in Heaven is Eric Clapton carrying an unbearable loss and somehow turning it toward grace. Fire and Rain has James Taylor tangled in loss and guilt at once, calling out for help. The heaviest entries are the ones where the person you would apologize to is no longer there to hear it, which is regret with no possible exit.
Not all of it is so stark. Same Old Lang Syne is Dan Fogelberg running into an old flame in a grocery store on Christmas Eve, the whole song a quiet inventory of the road not taken. My Way is Frank Sinatra admitting to a few regrets and then shrugging them off, which is its own kind of hard-won peace. The best regret songs know the feeling is not a place to stay. They sit in it long enough to feel it, then look for the door.
Related lists
Regret borders a few gentler subjects here. The forward motion out of it runs through songs about moving on. The deliberate act of putting it down fills songs about letting go, and the harder work of making peace with what happened lives in songs about forgiveness, which includes forgiving yourself.
If a line is stuck in your head, some verse about turning back time or a chance you missed, the search bar on our home page turns remembered words into titles quickly.
The songs here span from 1965 to the last decade, and the ache has not aged. Everyone eventually collects a few of these moments, the word unsaid, the exit taken too fast, and a good regret song does not fix any of it. It just proves someone else stood exactly where you are standing, wishing for the same extra day. That company is the point, and it is worth more than it sounds.