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10 Best Songs about Regret and Remorse

10 Best Songs about Regret and Remorse

In artistic terms, there can be little doubt that regret has remained one of the most popular themes addressed by pop songwriters. Sometimes falling in love means falling out of love. Sometimes risking it all means losing it all. Many of the following ten songs evoke the strong feelings of regret that often accompany breakups or the break-down of family relationships.

As these songs show, moreover, songs about regret can be one of the most powerful emotions that a musician can use to connect with an audience.

Best Songs About Regret

Phil Collins, “Against All Odds”

As everyone knows, it can be extremely difficult to move on from a relationship that hasn’t worked out, and Phil Collins knew intuitively that regret often constitutes the biggest part of a falling out with someone.

“Against All Odds” remains one of Collins’s most touching odes to lost love; for anyone who relishes a well-written ballad, it’s hard not to get weepy-eyed at this true heartbreaker of a song. Musically, “Against All Odds” remains one of the finest evocations of regret ever released.


Sade, “Is It A Crime”

As is often true in life, sometimes a breakup causes us to discover that our minds and our hearts are moving in different directions from one another. We know that we should move on with our lives, for example, but the emotional pull towards the object of our affections is still as strong as ever.

On “Is It A Crime,” Sade expresses this truth in the aptest and poetic way possible: Even by her own high songwriting standards, the song is profoundly moving.


Cat Stevens, “Father and Son”

Almost certainly one of the best songs about generational divides ever written, “Father and Son” by Cat Stevens describes the way in which our failure to connect with our families or live up to the expectations of others can often lead to deep regrets at a later time. While “Father and Son” certainly doesn’t feature Stevens at his most upbeat, the song does show us that we aren’t alone in our struggle to be heard and to make our own way in the world.


Gin Blossoms, Hey Jealousy

While the Gin Blossoms‘ song Hey Jealousy has a catchy chorus and was a chart-topper in the 90s, the lyrics actually talk about deep regrets. They tackle both ongoing alcohol abuse and failed relationship. With lyrics like:
Cause all I really wants to be with you
Feeling like I matter too
If I hadn’t blown the whole thing years ago
I might be here with you

It’s a sobering song about a lifetime of regrets and lost connections.

Elton John, “Goodbye Yellow Brick Road”

For most people, there comes a time in life when it becomes essential to lay aside the naiveté of youth. This process can elicit many feelings of regret, it is true, but casting away cherished illusions was never going to be an easy proposition for anyone.

Over the course of a scant three minutes, however, Elton John shows us that regret can be a powerful tool in eliciting personal change for the better. Not just a remarkable expression of regret, “Goodbye Yellow Brick Road” may just be John’s magnum opus as a songwriter.


ABBA, “Knowing Me, Knowing You”

One of ABBA’s biggest hits, “Knowing Me, Knowing You” describes the kind of regret that can emerge from the ashes of a dysfunctional relationship.

The band was in top form when the song was first released in 1976, and fans have since made it one of their most cherished ABBA tunes. Don’t let the upbeat pop production on the track fool you: This may just be one of the saddest songs ever written about the end of a relationship.


New Order, “Regret”

Formed from the ashes of Manchester rock band Joy Division, New Order adopted a deeply minimal sound throughout the 1980s that evoked the industrial landscape of their hometown.

With “Regret,” however, the band decided to flesh out their electronic sound with a decidedly bright and dense approach to pop production. Despite its sad subject matter, “Regret” became the band’s biggest hit after the song was released in 1993. The song remains a fan favorite at the band’s increasingly rare live shows.


Hall & Oates, “Out of Touch”

Bombastic 1980s synth pop doesn’t get much more intense than Hall & Oates’s 1984 hit “Out of Touch,” but the 80s production sheen on this standout pop tune masks the deep sense of longing that is expressed in the song’s lyrics.

Strangely enough, songwriter Daryl Hall didn’t think that “Out of Touch” would fit with his group’s sound. But after being convinced by a friend that the song could be a hit, the songwriter turned the track into one of Hall & Oates’s signature crowd-pleasers. Regret has never sounded quite as sweet as it does here.


Elliott Smith, “Ballad of Big Nothing”

It would be redundant to say that Elliott Smith often turned to melancholy subject matter over the course of his short musical career. But “Ballad of Big Nothing” is sad even by Smith’s woebegone standards.

Examining a string of broken relationships and disappointments with almost surgical precision, Smith uses the feeling of regret here as a vehicle to get to the core of human experience.

This is not easy listening by any means, but Smith’s incredible capacity for expressing a deep atmosphere of sadness via Paul McCartney-esque chord progressions and melodic whimsy really has to be heard to be believed.


Love, “Alone Again Or”

Another great song about the fallout from a breakup, “Alone Again Or” sees Love songwriter Arthur Lee attempt to remain optimistic even while he is struggling with feelings of isolation and regret.

Largely ignored by the general public when it was first released in 1967, the track has since garnered a reputation as a 1960s pop songwriting landmark among music aficionados. Moreover, “Alone Again Or” is undoubtedly the crown jewel in Arthur Lee’s legendary songwriting career.


XTC, “That’s Really Super, Supergirl”

XTC was one of the most promising acts to emerge from the British New Wave scene of the 1980s, but principle songwriter Andy Partridge was never quite at home with the notion of being a popular rock star.

A bad case of chronic stage fright sent the composer into a tailspin at the height of XTC’s career, but Partridge elected to use his time away from the stage to recreate the sounds of his favorite 1960s pop acts in the studio.

The results were a resounding success: In its melodic delineations on the theme of regret, “Supergirl” brought the psychedelic sensibilities of 1960s songwriters like Brian Wilson and John Lennon rushing into the clean-cut atmosphere of the 1980s pop world.

That Partridge was able to equal his musical idols remains one of music’s great feats.

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