10 Best Songs About Regret

Sad songs are often much better than happy songs; that's why every one of the 10 best songs about regret is an all-time great. From punk rock to hip-hop, these songs of sorrow may make you wonder if it's even worth it to go on, until you realize that great music was the result. Here are the 10 best songs about regret of all time:

  1. "Kiss the Bottle" by Jawbreaker. "I kissed the bottle. I should have been kissing you." Is there a line more filled with regret than that? This punk rock breakup song tops the list of the 10 best songs about regret.
  2. "The Mercy Seat" by Nick Cave & the Bad Seeds. Who has more regret than a condemned murderer waiting to take his place on the electric chair? Surely not many. Nick Cave's most enduring lament is told from the eye of one such prisoner. It is beautiful, poetic, sad, and scary; easily one of the best songs about regret in popular music history.
  3. "Private Eye" by Alkaline Trio. Another punk rock tale of woe, this regretful song details a New Year's Eve with no one to kiss and nothing to drink, except some "old rotten milk someone left in the sink." It ends like most of the best songs about regret, with its hero smoking himself stupid.
  4. "Regret" by New Order. A dance floor ditty, the feeling of regret in the title makes its way more through the lyrics than the music. That is what makes it a great but deceptive entry on this list of the 10 best songs about regret.
  5. "My Back Pages" by Bob Dylan. This is one of the songwriting master's most regretful tunes. He looks back on his past and shakes his head; hindsight is 20/20, even for a man as smart as Bob Dylan.
  6. "Roses" by Sheer Terror. This hardcore punk classic is a melodic masterpiece of despair. The Reverend Paul Bearer sings of a miserable year with dramatic irony.
  7. "Mockingbird" by Eminem. "Mockingbird," in which the star rapper lays out everything he's done wrong in the life of his only child. It's angry, heartbreaking, and funny at the same time, something that can be said about only the best songs about regret.
  8. "Remedy" by Hot Water Music. You can practically feel the despair coursing through the gruff vocals that begin this song and carry it through to the end. Teenagers will pump their fists to this tale of woe for decades to come.
  9. "Dreaming from the Waist" by the Who. Pete Townshend wrote this one about drinking too much and sleeping around. The best songs about regret are usually about nothing else.
  10. "Alone and Forsaken" by Hank Williams. The master of country regret gave us this, one of his most enduring songs. "Alone and Forsaken," fittingly, closes out this list of the 10 best songs about regret of all time.
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