21 Of The Best Songs About Regret And Mistakes

Written by Dan Farrant

Plenty of songs help celebrate life and all its beauty—but what about regret? What about the all-too-common human experience of remorse? That feeling that things could have or should have gone differently?

Thankfully, there is no shortage of songs that channel these feelings. Although there are plenty of happy songs, there is also an array of moving and funny tunes that express the feeling of looking back on things and wishing they’d been different.

What precisely that feeling is, or what it can mean, is up for interpretation. To find out the many dimensions of regret in music, you must learn by listening. And you can start with 21 of the best songs about regret. Read on!

1. “Yesterday” By The Beatles

The first entry on this list is perhaps the most famous regret song of all time. The Beatles‘ “Yesterday,” composed and written by Paul McCartney, is a moving ballad about the end of a relationship.

McCartney’s mellow vocals are set against a melancholic string quartet and acoustic guitar. This understated arrangement emphasizes the raw despair of the lyrics.

The singer laments that while his life was idyllic and harmonious as recently as yesterday, his life is now marked by heartbreak, loss, and pain. Now he wants to go back to yesterday when all was well.

2. “I Want You Back” By The Jackson 5

The next song on our list, by The Jackson 5, offers an opposing approach to regret. Whereas “Yesterday” is somber and lowkey, “I Want You Back” is a maximalist Motown tune that infuses an ironic joy into regret.

Sung by an adolescent Michael Jackson, “I Want You Back” captures the exuberant energy of begging for a lover to return to you. He expresses his regret when he took her for granted and realizes too late what he’s missing.

The lyrics express a real pain at the loss of a loved one. The singer is reduced to begging to be given a second chance at love.

3. “Hurt” By Nine Inch Nails

Our next song, Nine Inch Nails‘ “Hurt,” is perhaps the most visceral song about regret on this list. With instrumentals that cross eerie strings with industrial rock distortion, the song is haunting enough without even listening to the lyrics.

But if you attend to the melancholic lyrics, your experience of the song will go up a notch. The moody, angst-filled speaker mourns he has lost everyone that matters in his life. He has been alienated from himself, and his achievements have been reduced to nothing.

The song drips with the regret of a man looking back on decades of life. He finds himself asking, “What have I become?”

4. “Butterfly” By Weezer

The next entry on our list is a song that mentions “regret” in the form of “I’m sorry.” Weezer‘s “Butterfly” is an emotional dirge set against the backdrop of a simple acoustic guitar.

“Butterfly” culminates the emotional arc of Pinkerton. This album sees each song’s speaker struggling to establish healthy human connections. In this case, the singer apologizes to an unnamed woman whom he has hurt.

The butterfly in the song is a metaphor for the woman. He catches the “fairy pet” and imprisons it in a mason jar. This alludes to him keeping the woman a prisoner of his love. Perhaps he doesn’t know how to love a woman, thus ending in a dying relationship.

5. “u” By Kendrick Lamar

Going back to songs of emotionally intense regret, we find “u” one of the central tracks from Kendrick Lamar‘s smash-hit album To Pimp a Butterfly.

“u” begins with Lamar screaming intensely, and the energy only ramps up from there. He intermingles immaculately constructed verses with sniffing, crying, and screaming. He also laments his failures and regrets before God and his public.

Then, in one of the most memorable moments of the song, he speaks directly to a deceased friend of his. A friend who had died while Lamar was on tour.

Although the album’s emotional trajectory restores Lamar to some degree of health, “u” is one of the most vivid expressions of regret in all hip-hop.

6. “Ms. Jackson” By OutKast

Some regrets eat into our souls, but most of the time, we have mixed feelings. Do we really regret them, or do we simply regret the consequences? OutKast‘s “Ms. Jackson” channels this exact feeling into a mixture of remorse and rollicking fun.

In the song, “Ms. Jackson” is the mother of the singer’s ex. He confesses that he did not intend to cause her daughter misery or dismay. However, he insists they will be better apart.

The song is so brilliant because it captures the social dimension of regret and the difficulty of making amends. If the catchy lyrics and bump-worthy beats are any indications, apologizing might be more upbeat than it seems.

7. “Back To December” By Taylor Swift

Being the undisputed queen of relationship postmortem should be included in Taylor Swift‘s resume, at least in the world of music. Usually, her songs are expressions of anger or rage after being jilted by a lover. But “Back to December” flips the script.

In the song, the singer laments the cruelty with which she ended a relationship. She regrets rejecting his love, having realized over the year that he was the one for her.

The end of the song is especially moving, with her begging him to take her back. At the same time, she concedes that she would understand if he refused. Unfortunately, the song ends before we can learn any answer.

8. “Cat’s In The Cradle” By Harry Chapin

If there is a Mount Olympus for songs of regret, “Cat’s in the Cradle” belongs in one of the highest godly thrones. The song is Harry Chapin‘s essential entry in the folk rock genre, but it is also one of the canonical odes to regret.

The song narrates the experience of a father who does not make time to spend with his son from birth. As the boy grows up, the father continually finds reasons not to spend time with him. In his old age, the father experiences the desire to reconnect with his son. But now, his son is too busy to spend time with him.

Despite its simple story, Chapin’s arrangement is incredibly moving. It successfully emphasizes the tragedy of lost parental love.

9. “Sing About Me, I’m Dying Of Thirst” By Kendrick Lamar

Rapper Kendrick Lamar knows regret too well that two of his songs appear on this list. “Sing About Me, I’m Dying of Thirst” parallels “u” in that it comes at the emotional low point of its album.

But the similarities stop there. “u” is an intimate trip into Lamar’s experience of stardom. But “Sing About Me, I’m Dying of Thirst” is a panorama of his dire upbringing and escape from cycles of violence.

In the song, the opening depicts the temptations to violence. The second half of the song shows Lamar’s regrets for his many songs—culminating in a moving spiritual catharsis at the conclusion.

10. “Oops!… I Did It Again” By Britney Spears

With a mesmerizing melody and an iconic music video, Britney Spears‘s “Oops!…I Did it Again” is a pop culture classic. But listen closely and you’ll realize that the song is occupied with the ambivalence of regret.

In the song, the singer laments that she has broken his heart, continuing a long-term pattern of doing so. Though she is not as innocent as she seems, she still expresses regret for his emotional wounds.

The song gives us a glimpse of a person who is resigned to her wrongdoings and who regrets only in a perfunctory way.

11. “No Regrets” By Aesop Rock

There are only a handful of songs with “regret” in the title, and Aesop Rock‘s “No Regrets” is one of them. This song is a tale of a woman named Lucy who is disconnected from other people to the point that they think she’s crazy. But they know nothing.

The song starts when Lucy is seven, “born into this world with… no regrets.” She’d rather draw on the street with her yellow chalk than play with other kids. She grows up to be introverted, preferring the company of her charcoal sticks.

In her old age, we find out that Lucy lived a purposeful life as an artist. She tells the nurse she has no dream, meaning to say that dreams are the things you haven’t pursued. But Lucy has done what she wanted and dies with no regrets.

12. “How To Save A Life” By The Fray

The 2005 hit “How to Save a Life” might be best known for its status as a quintessential song in Grey’s Anatomy. But this single by The Fray is so much more than that. It is a musical anatomy of grief and a moving lament of how few things we can control.

The lyrics open with a potential reconciliation or conversation between friends. However, as the mellow piano chords progress into a soaring wall of sound, the lyrics turn to regret and despair as communication between people breaks down.

The tune is a heartbreaking testament to the beauty and agony of those experiences that we regret.

13. “Billie Jean” By Michael Jackson

In our next song, “Billie Jean,” the singer regrets not thinking twice before making decisions. The song comes from Michael Jackson‘s 1982 album Thriller.

“Billie Jean” is not a dirge or mournful ballad like many songs on this list. Instead, it expresses regret in a much more frantic, paranoid way. It charts the story of a man’s experience with a woman who seduced him and claimed to have mothered his child.

The singer probably regrets not listening to the advice of people around him. They warn him to “be careful of what you do.” The song ends with him denying that Billie Jean’s son is his.

14. “The River” By Bruce Springsteen

Here’s one fun fact about Bruce Springsteen. He has no shortage of songs about regret. It seems like half of his discography is dedicated to broken dreams! However, “The River” is one of his finest lamentations for the past.

A tale of lost innocence, “The River” tells the story of a promising young man who falls in love in high school. His dreams crumble when his girlfriend becomes pregnant. They marry, and he takes up manual labor and suffers under poor economic conditions.

He ends up regretting a lot of things in his life. He returns to the river to escape, knowing it’s already dried up, much like his dreams.

15. “A Couple Acres Greener” By Mipso

North Carolina folk-rock band Mipso is a newer act than some groups on this list. Still, they are no less talented at channeling the raw power of human emotions. One of which is regret, as evident in “A Couple Acres Greener.”

The song represents the moral agonies of a young man struggling to find his place in the world. He is faced with uncertainty over his vagabond lifestyle. And so he envisions a life where he might have tilled the land or worked as a preacher—anything to make the world better before he dies.

With haunting string instrumentals and a multi-piece vocal arrangement, Mipso can capture the spiritual sorrow—and intense musicality—of regret as an existential concern.

16. “Are You Lonesome Tonight” By Elvis Presley

American singer Elvis Presley is one of the most famous philosophers of broken hearts in musical history. “Are You Lonesome Tonight” demonstrates why.

The lyrics find the singer pining for a lost lover and wondering whether she misses him. He wants to know if she remembers the time they had together and whether she regrets how their relationship ended.

The latter half consists of a spoken-word performance showing the depths of the singer’s despair. He blames himself for not seeing through her lies. But he also admits that he’d rather hear her lies than live without her.

17. “Before He Cheats” By Carrie Underwood

The next song on this list is about regret, but not the singer’s regret. On the contrary, it is about the regret the singer hopes to inspire. Carrie Underwood‘s “Before He Cheats” is a warning to those who even think about cheating. You’ll regret it in the end, is what the song is saying.

And so the scorned woman goes on an act of revenge. She ruins his beloved car by keying it on the side and breaking the headlights. He slashes his tires and leaves a souvenir in the form of her name “carved… into his leather seats.”

He’s going to have to think twice before cheating again. But if he does, it won’t be on her anymore.

18. “Whatcha Say” By Jason Derulo

Up next is a fitting complement to Carrie Underwood’s “Before He Cheats.” Jason Derulo‘s “Whatcha Say” represents the other side of the infidelity equation.

In the lyrics, the singer apologizes to his lover for cheating on her. Although he admits that he’s wrong, he insists it was a moment of weakness that he strayed from their relationship. As is always the case with regret, it’s only later he realizes that he should have treated her better.

Now he’s asking for a second chance “to really be a man.” The chorus partially captures her response—which, despite the singer’s regret, is doubtful at best.

19. “Here Comes My Baby” By Yusuf/Cat Stevens

Another more upbeat song of regret appearing on our list is Yusuf‘s “Here Comes My Baby.” The high energies set up the track’s most fascinating contrast.

Lyrically, the song tells the regrets of a man who mourns the loss of his lover. Worse, she is now seeing a new beau. He knows she is with someone who can better take care of her.

However, that does not stop him from doing all he can to take her back. Or from waiting for her to love him again, even knowing that it’s useless.

20. “Would’ve, Could’ve, Should’ve” By Taylor Swift

Another song about regret from Taylor Swift‘s discography is “Would’ve, Could’ve, Should’ve.” This single was one of her most recent works that belong in her 2022 album Midnight.

What stands out from the song is the line, “I regret you all the time.” We can only guess how hurt the singer is by that declaration.

Notably, she recalls falling in love with him when she was 19. But now she regrets ever having a relationship with this ex. She calls him a “ghost” who haunts her to this day.

21. “If I Could Turn Back Time” By Cher

The final song on this list is another entry into relationship regret songs. In Cher‘s “If I Could Turn Back Time,” the singer laments that she cannot turn back time and take back the cruel words she spoke to an ex-lover.

With the use of a power ballad, “If I Could Turn Back Time” becomes an empowering and powerful tune. Here, the singer is full of regret for using her pride and words to break her ex’s heart.

She lets him know her willingness to do everything to get him back, even trying to “reach the stars.” She’ll make him stay if only she could turn back the time. But then, it’s too late for her to make amends.

Summing Up Our List Of Songs About Regret

Regret is such a powerful emotion. But unlike other emotions, such as love, regret comes only after mistakes have been done. And more often, it’s too late to right the wrongs.

Hopefully, the songs above taught a lesson on what to do to avoid regret in the end. Before you speak, think twice. Before you hurt someone, make sure you’re ready to face the consequences.

Because when all is said and done, regret can gnaw at you and leave you longing for peace of mind.

Photo of author

Dan Farrant, the founder of Hello Music Theory, has been teaching music for over 15 years, helping hundreds of thousands of students unlock the joy of music. He graduated from The Royal Academy of Music in 2012 and then launched Hello Music Theory in 2014. He plays the guitar, piano, bass guitar and double bass and loves teaching music theory.