27 Top Songs About Guilt, Regret, & Mistakes [You Might Be Able to Relate To]

Guilt, regret, and mistakes can come from lots of different circumstances and cause tons of often conflicting feelings. Whether the regret comes from cheating on a lover or disappointing your mom, there are songs about guilt for any mistakes that haunt your past.

“Alive” by Pearl Jam

Song Year: 1991

Pearl Jam's grunge hit tells the story of a boy finding out the man he thought was his father is actually not. As if that realization wasn't bad enough, he must later deal with his mother's strange advances.

Yet, throughout the devastating trauma that his mother has put him through, he still must go on because he's still alive, even if he doesn't want to be.

This early 90s song shows that sometimes the guilt and mistakes of others transfer over onto us.

“All Apologies” by Nirvana

Song Year: 1993

Nirvana frontman Kurt Cobain was known for his enigmatic lyrics, and “All Apologies” is no exception.

Cobain writes about a person who takes the blame for everything, whether it was their fault or not. A conflicted song that pairs relaxing imagery and an upbeat key with a dismal personal outlook, this alt-rock single showcases Nirvana's punk inspirations.

Also, recorded only a year before Cobain took his own life, the song's message of dealing with an immense amount of guilt resonates even more with fans.

“Always on My Mind” by Willie Nelson

Song Year: 1982

Willie Nelson's 1982 cover of a Gwen McCrae song from a decade earlier, “Always On My Mind,” describes a person who ponders the end of a relationship.

Nelson's song is full of ‘maybe's and ‘should's as he explores the reasons why his lover could have left him. Did he not give her the love she needed? Was he not the man she wanted?

This country ballad follows the same patterns of thought that most people have when a relationship ends as they wonder what they could have done better.

“Back to December” by Taylor Swift

Song year: 2010

Taylor Swift's 2010 country-pop single, both written and recorded by Swift, lives in a similar vein to Nelson's “Always On My Mind.” The main difference here is that Swift knows why her relationship collapsed.

“Back to December” shows that sometimes we just aren't in the right mind frame at a specific time to love someone how we should. Instead, by the time we've figured ourselves out, the other person has already moved past us.

“Because of You” by Kelly Clarkson

Song Year: 2005

As the winner of the first American Idol, Kelly Clarkson was at the height of her fame when she released “Because of You.” This poignant pop song highlights the damage that an adult can do to a child even after that child has grown up themselves.

Another single that analyzes the way someone else's mistakes can affect us, “Because of You,” is a song that shows us that even though abusers may damage us, they cannot break our spirits.

“Cat's in the Cradle” by Harry Chapin

Song Year: 1974

Harry Chapin, the original singer and songwriter of “Cat's in the Cradle,” follows a man from his son's birth to the boy's adulthood. In this folk-rock song, Chapin recounts every parent's worst nightmare of finding out that you've missed out on your child's life.

The father in the song worries so much about his own work and his own life that he continuously puts his son off when his son wants to spend time with him. By the end of the song, once he finally has time for his son, his son has turned into the same absent-minded person as his father.

“Don't Let Me Get Me” by P!nk

Song Year: 2002

Early 2000s pop singer P!nk sings about the stress and insecurity that past mistakes can cause. Even with the immense success that P!nk has had, her troubled formative years still haunt her.

From letting down her parents to the difficulties that arise when everyone knows your name, “Don't Let Me Get Me” explores the way that mistakes can fill us with regret and guilt even years later.

“The Freshmen” by Verve Pipe

Song Year: 1997

The alt-rock band Verve Pipe's late 90s hit tells the story of two young people struggling with the decision to have an abortion. The boy in the song claims that the incident can't really be their fault because of their age, but the guilt still consumes the two.

The heartbreaking song about young people dealing with painful decisions they aren't ready for came from a true story. Brian Vander Ark, the song's writer, explained that the lyrics originated from his ex-girlfriend's decision to terminate her pregnancy.

“Give It Away” by George Strait

Song Year: 2006

One of George Strait's many number one singles, “Give It Away,”‘s mixture of the song's woman's exasperation and the man's depression can easily resonate with many people who have had relationships end badly.

In this song, like often in life, one partner is so done with the other that they don't even want to fight to get their stuff, while the other is left to absorb the heartbreak.

“Guilty” by Marina and the Diamonds

Song Year: 2010

Although more popular in the United Kingdom than the United States, Marina and the Diamonds has released a plethora of songs about guilt, regret, and mistakes.

“Guilty” uses vague lyrics that only give the listener the bare minimum of the story. We don't get a good understanding of the details of what is upsetting her. Instead, the song uses the beating of a rare dog as a metaphor for her childhood mistakes.

“Heartless” by Kanye West

Song Year: 2008

Kanye West's “Heartless” recounts the conflicting and confusing feelings after a break-up where you can sometimes feel both like you're better off without the other person and that you can't live without them.

As one of Kanye's most recognizable singles, “Heartless” is a relatable song about how mistakes can deteriorate a relationship.

“How Could You Leave Us” by NF

Song Year: 2016

It isn't often that you can hear a rapper break down and cry during their recording, but the emotionally fueled lyrics of Christian hip-hop artist NF's “How Could You Leave Us” are about as raw as you can get.

In the 2016 song, NF raps about the pain he felt throughout his childhood from his mother's drug addiction and absence. NF wrote the song not long after his mother died of an overdose, and, in the track, he grapples with his feelings of rage and regret at their rocky relationship.

“Hurt” by Johnny Cash

Song Year: 2003

In one of Johnny Cash's last albums before his death, he covers Nine Inch Nails' 1995 song “Hurt.” Cash's version of the song became so popular that many people still believe that he is the original performer.

“Hurt” is a bleak story that combines depression, guilt, addiction, and self-hatred but surprisingly ends on a note which gives the listener a bit of hope that things can get better.

“I Miss You” By Blink-182

Song Year: 2004

Blink-182's “I Miss You” has become one of the defining songs of the early 2000s emo genre.

In true emo fashion, the song uses the imagery of spider webs, death, and “The Nightmare Before Christmas” (1993) to describe the pain of losing a lover. The singer's voice pleads with his lost lover to come back to him despite the pain she has put them through.

“Jane Says” by Jane's Addiction

Song Year: 1988

“Jane Says” introduces the listener to Jane, who, throughout the song, struggles to find her path in life. In the beginning, she leaves her abusive boyfriend, but, despite this big step, she is left confused and alone.

Jane attempts to get her life together so she can live it for herself, but her past mistakes and circumstances consistently hold her back.

“Like a Rolling Stone” by Bob Dylan

Song Year: 1965

Despite initial pushback from Columbia Records, who were skeptical of the song, Rolling Stone magazine ended up listing “Like a Rolling Stone” as the greatest song of all time.

In the six-minute folk-rock classic, Bob Dylan tells the life of a girl who fell from the heights of society and must now fend for herself in the big scary world. The song describes her regret at how she must now roam the streets to make a life for herself instead of having other people make things easy for her.

“Lucid Dreams” by Juice WRLD

Song Year: 2018

Juice WRLD's 2018 emo-rap single “Lucid Dreams” is the rapper's contribution to the plethora of songs about lost love and what could have been.

Surprisingly upbeat, the song uses the concept of lucid dreams to describe the feelings he encounters when he questions his relationship with his past love and wonders if he made a mistake in choosing his ex-girlfriend, who he thought he would marry.

Mama Told Me (Not To Come) by Three Dog Night

Song Year: 1970

As probably the most humorous song on this list, “Mama Told Me (Not To Come)” reflects the realization that maybe your mom really did know more than you thought she did.

The Eric Burdon and the Animals song made famous by Three Dog Night's cover tells the story of a young man who goes to a party despite his mother telling him it's a bad idea. At the party, he ends up seeing things he never wanted to and regrets not listening to his mama's advice.

“Mama Tried” by Merle Haggard

Song Year: 1968

Country legend Merle Haggard's late 1960s single describes that awful feeling felt time and time again, disappointing your mama.

Haggard's main character in his song ends up in prison after his mother did everything she could to raise him right and keep him on the correct path. The man also has to come to the realization that all the trouble that he's gotten himself into in his life is his own fault because his mom gave him everything she could.

“The One That Got Away” by Katy Perry

Song Year: 2011

As the title suggests, this Katy Perry hit describes the regret of losing the one who you thought was your soul mate. The majority of the song tells about how perfect she and her lover were for each other. Still, the chorus and other sections let the listener in on the mistakes that destroyed what should have been a perfect relationship.

“Oops!… I Did It Again” by Britney Spears

Song Year: 2000

“Oops!… I Did It Again” from Britney Spears's second studio album explains the guilt of having someone love a version of yourself that isn't real. The level of infatuation the person feels for her appears in the Titanic reference in the song's middle, where they bring her the Heart of the Ocean.

Whether she really meant to deceive the person who fell in love with her isn't entirely clear, but the guilt that comes from playing with someone's emotions is evident throughout the song.

“Suicidal Thoughts” by Notorious B.I.G.

Song Year: 1994

In true Biggie fashion, “Suicidal Thoughts” isn't for everyone. The mid-90s track from the aptly titled album “Ready to Die” explores some of the most painful feelings that a person can have to deal with, the urge to take one's life.

Throughout the song, Biggie describes the awful things that he's done in his life and concludes that he'd rather just end it and go to hell. A raw song with some of the most self-deprecating lyrics that music has ever seen, “Suicidal Thoughts” lives up to its name.

“Unfaithful” by Rhianna

Song Year: 2006

One of Rhianna's first popular songs, “Unfaithful,” is about the guilt and regret of cheating on a partner.

Even though the man knows that she is violating his trust and she feels horrible about what she puts him through, the cheating still continues as it eats both of them alive.

“What Goes Around… Comes Around” by Justin Timberlake

Song Year: 2006

“What Goes Around… Comes Around” was one of the biggest songs of Justin Timberlake's solo career. A song similar to “Cry Me A River,” which came out a few years earlier, this 2006 hit is where Timberlake must deal with the regret that comes from a failed relationship.

Like many of the songs that came before it, “What Goes Around… Comes Around” explores the conflicting emotions that arise when a serious courtship ends.

In this pop song's lyrics, Timberlake talks about how, in hindsight, he should have known that his love was going to break his heart.

“When I'm Gone” By Eminem

Song Year: 2005

Eminem is both famous and infamous for openly rapping about the troubles he experiences in his family. “When I'm Gone” follows that trend.

In the track, Eminem opens up to fans about how fame has damaged the bond between him and his daughter because of his constant commitments to fans. The single is full of regret and guilt aimed at himself and his mistakes as he questions whether he has been a good father.

“Wrong Way” by Sublime

Song Year: 1997

The main character in the song “Wrong Way” is definitely a bad guy. From murder to illicit sex, he continuously goes down the wrong path even though he's aware he's making bad decisions.

But, by the end of the song, there is no turnaround or awakening for the main character. Instead, the man continues with his wrong decisions and poor moral compass even though it makes him feel guilty, and he regrets his choices.

“You Found Me” by Fray

Song Year: 2008

The Fray's 2008 alternative rock song, “You Found Me,” explores the black hole that loss can bring upon us and the guilt and regret we may feel at someone's sudden exit from our lives.

Isaac Slade, the primary writer of The Fray's music and lyrics, explained in a 2009 interview that the song is also about the arguments between yourself and God that can blossom during extreme pain.

Best Songs About Guilt, Final Thoughts

As these songs about guilt show us, the feeling of regret can come from many different places. Have you hurt the people you loved? Or, maybe you've ruined a relationship with someone you really cared about? Guilt can even come to us through others' mistakes, but however these feelings have caught up with you, there's a song that can give you solace.