20 Songs About Regret And Mistakes

Life is full of choices and paths we don’t take, so it’s no surprise that sometimes we feel sorry about the decisions we made and the ones we didn’t.

Regret can hurt a lot. It’s when we feel sorry, disappointed, guilty, or remorseful about things in the past, and these feelings can affect our lives now. It’s tough to explain.

Luckily, there are plenty of songs that capture the feeling of looking back and wishing things were different.

If you want to explore the different sides of regret in music, start by listening. Here are 20 great songs about regret. Keep reading!

20 Songs About Regret And Mistakes

1. “I Want You Back” By The Jackson 5

“I Want You Back” by The Jackson 5 is an upbeat Motown song sung by a young Michael Jackson. It tells the story of regret and the desire to reunite with a lost lover.

The singer reflects on taking his partner for granted when they were together and now realizing the mistake with lines like, “When I had you to myself, I didn’t want you around.”

The lyrics express a sense of longing and a plea for a second chance at love, as the song repeatedly declares, “Oh, baby, give me one more chance (to show you that I love).”

2. “Yesterday” by The Beatles

“Yesterday” by The Beatles, composed and written by Paul McCartney, is a poignant ballad that reflects on the end of a relationship. McCartney’s soft vocals are accompanied by a melancholic string quartet and acoustic guitar. The song expresses the singer’s deep sense of regret and longing for the past.

The singer reflects on a time when all his troubles seemed distant, but now he feels overwhelmed by heartbreak and loss. He laments that he’s no longer the person he used to be, as a shadow hangs over him. The lyrics emphasize the desire to turn back time to a happier, more harmonious past with lines like, “Oh, yesterday came suddenly.”

The song also touches on the mystery of why the relationship ended, with the singer wondering why his partner had to leave and expressing regret for saying something wrong. The refrain, “Now I long for yesterday,” captures the profound sense of loss and yearning.

3. “Hurt” by Nine Inch Nails 

“Hurt” by Nine Inch Nails convey a sense of self-inflicted pain and emotional turmoil. The singer describes intentionally hurting himself to feel something real, focusing on the physical pain as a way to escape emotional numbness. The reference to a needle tearing a hole suggests substance abuse as a coping mechanism.

Despite the attempts to numb the pain, the singer acknowledges that he remembers everything, which means his emotional scars and regrets persist.

He laments that everyone he knows eventually goes away with lines like, “What have I become? My sweetest friend, Everyone I know goes away In the end.”

4. “Ms. Jackson” By OutKast

“Ms. Jackson” by OutKast is a track from OutKast’s album “Stankonia,” released in 2000. The song became a major hit and is known for its catchy melody and distinctive lyrics.

It’s a song that reflects on the complexity of regret and the consequences of past actions. In the song, the narrator addresses the mother of his ex-partner, expressing remorse for the pain and sorrow he unintentionally caused her daughter.

The lyrics begin with the narrator apologizing to “Ms. Jackson” and emphasizing his genuine regret, stating, “I’m sorry Ms. Jackson (ooh), I am for real, Never meant to make yo’ daughter cry, I apologize a trillion times.”

The song captures the essence of mixed feelings, as the narrator acknowledges the difficulty of the situation and attempts to make amends.

5. “u” by Kendrick Lamar

“u” by Kendrick Lamar is a powerful and emotionally intense track from his album “To Pimp a Butterfly.” The song stands as one of the most vivid expressions of regret in hip-hop.

In the lyrics, Kendrick confronts someone, possibly himself or a close friend, with harsh criticism and blame, accusing them with lines like, “You ain’t no brother, you ain’t no disciple, you ain’t no friend.”

He expresses deep regret and sorrow as he addresses a deceased friend, questioning where he was when his friend needed him the most, and lamenting his failure with lines like, “Third surgery, they couldn’t stop the bleeding for real, Then he died, God himself will say, ‘You fuckin’ failed,’ you ain’t try.”

6. “Butterfly” by Weezer

“Butterfly” by Weezer is a poignant and introspective song that serves as the closing track for their album “Pinkerton.” In this song, the singer reflects on his actions and expresses regret for hurting someone he cares about. 

The song begins with the singer reminiscing about catching a butterfly in a mason jar, which is used as a metaphor for capturing and confining someone’s love: “Yesterday I went outside with my Mama’s mason jar, Caught a lovely butterfly.” As time passes, he realizes that his actions have caused harm and suffering to the person he cares for, symbolized by the withering butterfly.

The singer expresses his sincere apology for the pain he has caused, acknowledging that he didn’t intend to harm the other person: “I’m sorry for what I did, I did what my body told me to, I didn’t mean to do you harm.” 

7. “Back to December” by Taylor Swift

“Back to December” by Taylor Swift is a heartfelt song in which the singer reflects on a past relationship and expresses deep regret for how she treated her former partner.

The song carries a sense of longing and a desire for reconciliation. In the lyrics, the singer acknowledges the pain and hurt she caused in the past when she left him with lines like, “You gave me roses and I left them there to die.”

The singer admits her mistakes and expressing a yearning to go back to the past and make things right, stating, “I go back to December all the time, It turns out freedom ain’t nothin’ but missin’ you.”

8. “Cat’s in the Cradle” by Harry Chapin

“Cat’s in the Cradle” by Harry Chapin is a poignant and timeless folk rock song that tells the story of a father and son and the regrets that unfold as their lives diverge. The song serves as a powerful reflection on the consequences of neglecting precious moments with loved ones.

The lyrics begin with the narrator describing the birth of his son and the subsequent demands of life that kept him away. As the boy grows up, he expresses the desire to be like his father, who is often absent due to work and other obligations. The recurring line “I’m gonna be like you, dad” reflects the son’s admiration for his father.

The song features the metaphor of “the cat’s in the cradle and the silver spoon,” symbolizing the fleeting nature of time and the missed opportunities for connection.

9. “No Regrets” by Aesop Rock

“No Regrets” by Aesop Rock is a poignant song that tells the story of Lucy, a woman who lived her life on her own terms without regret. The song begins when Lucy is just seven years old, described as a city-born child with no knowledge and no regrets, singing, “City born, into this world with no knowledge and no regrets.”

Lucy spends her time drawing on the sidewalk with yellow chalk, capturing the faces of the people she encounters. As she grows older, she remains introverted, finding solace in her art, particularly charcoal drawing. 

In her later years, Lucy resides in a senior home, having traded her locks and clips for a headrest and her charcoal sticks for arthritis. She reminisces about her past, filled with art and solitude.

Lucy imparts a valuable lesson as she reflects on her life to a nurse, saying that she never had a dream but lived her life pursuing her passions and desires. She has no regrets because she became the dream she wanted to be from the beginning. 

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

“Oops!…I Did It Again” by Britney Spears is a pop hit known for its catchy melody and iconic music video. However, beneath its pop culture allure, the song delves into the ambivalence of regret.

The singer acknowledges that she has once again broken someone’s heart, continuing a pattern of doing so, as she sings, “I think I did it again, I made you believe we’re more than just friends.”

Despite not being as innocent as she may appear, she still expresses regret for causing emotional pain to her romantic interest. The song provides a glimpse of a person who is resigned to her own wrongdoings and expresses regret in a somewhat perfunctory manner.

In the lyrics, the singer admits to her recurring actions and the confusion they create, singing, “Oops, I did it again to your heart, got lost in this game, oh baby.” 

11. “Billie Jean” By Michael Jackson

The song “Billie Jean” by Michael Jackson, featured on his 1982 album Thriller, tells a story of regret in a frantic and paranoid way.

It describes the encounter of a man with a woman named Billie Jean, who seduces him and claims that he is the father of her child. The man regrets not heeding the warnings of those around him who advised him to be cautious about his actions.

He denied that Billie Jean’s child is his, despite her persistent claims, with lines like “Billie Jean is not my lover, She’s just a girl who claims that I am the one, But the kid is not my son.”

12. “How To Save A Life” By The Fray

The song “How to Save a Life” by The Fray, released in 2005, gained popularity partly because of its feature on the TV show Grey’s Anatomy. It’s more than just a catchy tune; it’s a heartfelt exploration of grief and the inability to control certain aspects of life.

The lyrics begin with a conversation between two friends who need to talk, with lines like “Step one, you say, ‘We need to talk'” and “He walks, you say, ‘Sit down, it’s just a talk’.” There’s an attempt to reconcile, but as the song progresses with its mellow piano and emotional build-up, the lyrics turn towards regret and despair. The breakdown in communication becomes evident, with lines like “And where did I go wrong? I lost a friend.”

The song reflects on the feeling of losing a friend and wondering where things went wrong, with lines such as “Somewhere along in the bitterness.” It’s a lament for not being able to save the friendship, as seen in the lines “Had I known how to save a life.” The singer expresses a willingness to stay up all night if they had known how to salvage the relationship.

13. “A Couple Acres Greener” By Mipso

In “A Couple Acres Greener” by the North Carolina folk-rock band Mipso, the lyrics tell the story of a young man who grapples with regret and existential concerns about his life choices.

The song begins with the narrator expressing his hunger for something more, with lines like “I’ve never been so hungry” and “Seems like twenty-two years I’ve been looking for a fight.” He acknowledges his restlessness and inability to find his path, having never stayed in one place for too long.

In the end, he regrets not becoming a preacher or a farmer, roles that would have allowed him to contribute to the world in a meaningful way, as expressed in lines like “Should have been a preacher man” and “Should have been a farmin’ man.”

14. “The River” By Bruce Springsteen

“The River” by Bruce Springsteen is a poignant song that reflects on a young man’s life marked by regret and lost dreams. In this song, the narrator hails from a working-class background in a valley. He recalls his youth when he met Mary in high school at the age of seventeen.

The lyrics recount how their love blossomed, with idyllic scenes of riding down to the river and diving into its waters. However, their dreams take a sharp turn when Mary becomes pregnant, and they hastily get married, leaving behind the dreams of youth.

The joy of a traditional wedding is replaced by a courthouse ceremony, devoid of smiles, flowers, or a wedding dress. As the years pass, the narrator takes up a construction job like his father, but economic hardships lead to fewer opportunities for work. The dreams and ambitions he once had start to fade away. 

Memories of his happier times by the river haunt the narrator, making him question whether dreams are merely illusions, as expressed in lines like “Is a dream a lie if it don’t come true, Or is it something worse?”

Throughout the song, the narrator expresses his regrets over missed opportunities and the burden of unfulfilled dreams.

15. “Are You Lonesome Tonight” By Elvis Presley

Are You Lonesome Tonight” by Elvis Presley is a classic song that reflects the pain of lost love and the lingering memories of a past relationship.

The lyrics begin with a series of questions, as the singer wonders if the person he’s addressing is feeling lonely and missing him, with lines like “Are you lonesome tonight?” and “Do you miss me tonight?”

He reminisces about the happy moments they shared in the past, like kissing on a bright summer day, as expressed in the lines “Does your memory stray to a bright summer day when I kissed you and called you sweetheart?”

The singer recalls how their love story began and how they fell in love at first sight; however, things changed, and the person he loved seemed to act differently, which left him confused and hurt.

The singer blames himself for not confronting the fact that his lover lied about loving him because he didn’t want to live without her. He sings, “Honey, you lied when you said you loved me, and I had no cause to doubt you, but I’d rather go on hearing your lies than go on living without you.

16. “Somebody That I Used to Know”

“Somebody That I Used to Know” by Gotye featuring Kimbra explores the aftermath of a breakup, reflecting on the complexities of past relationships and the regrets that may linger.

The lyrics open with reminiscences about the time when the narrator and their former partner were together. The lines “Told myself that you were right for me, But felt so lonely in your company” hint at the narrator’s regret for not realizing the true nature of their relationship earlier.

With this feeling of remorse still haunting him, the singer portrays the pain of their lost love as “an ache I still remember.”

17. “All Apologies” by Nirvana

“All Apologies” is a song by the American rock band Nirvana, written by the band’s iconic vocalist and guitarist, Kurt Cobain. The song serves as the final track on Nirvana’s third and last studio album, “In Utero,” which was released by DGC Records in September 1993.

The lyrics of “All Apologies” reflect a sense of introspection and self-reflection. Kurt Cobain expresses a feeling of remorse and self-doubt, pondering what he should be or say in the face of various circumstances.

In the lines “What else should I be? All apologies” it appears that Cobain is acknowledging his imperfections and seeking forgiveness for some mistakes. 

18. “Would’ve, Could’ve, Should’ve” by Taylor Swift

“Would’ve, Could’ve, Should’ve” by Taylor Swift is a song from her 2022 album “Midnight.” In this song, Taylor reflects on her past relationship, expressing regret and longing for a different outcome.

The lyrics touch on moments when she wishes things had gone differently, with lines like “If you would’ve blinked then I would’ve looked away at the first glance” and “If you never touched me, I would’ve gone along with the righteous.”

Taylor sings about how she met this person when she was 19 and how, looking back, she regrets ever getting involved with them, saying, “And I damn sure never would’ve danced with the devil at nineteen.”

She describes this person as a “ghost” who continues to haunt her, and the song conveys the idea that sometimes we make choices that lead to pain and regret.

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

Cher’s “If I Could Turn Back Time” is a powerful power ballad that delves into the theme of regret in a relationship. In the song, Cher expresses her deep regret for the hurtful words and actions that led to the breakup with her lover. 

The lyrics convey her sincere remorse, with lines like “If I could turn back time, I’d take back those words that have hurt you.” She acknowledges that her pride and hurtful words were like weapons that wounded her partner and led to their separation.

Cher’s desperation to make amends is evident in the lines, “If I could reach the stars, I’d give ’em all to you, then you’d love me, love me like you used to do.” She is willing to go to great lengths to win back her lover’s affection, even attempting to do the impossible if it would mean a chance to make things right.

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

In the song, “Here Comes My Baby,” the singer expresses his feelings of longing and regret after losing his lover. He knows that she has moved on and is now with another man, someone who can take better care of her. Despite this knowledge, he can’t help but hope for a chance to win her back, even though he knows it’s unlikely to happen.

The lyrics describe the narrator’s late-night walks filled with loneliness, as he can’t stop thinking about his lost love. He keeps seeing her in his mind and can’t escape the image of her, as he sings, “In the midnight moonlight I’ll be walking a long and lonely mile.” The recurring line “Here comes my baby, here she comes now” reflects the bittersweet feeling of seeing her with someone else.

The narrator acknowledges that he has tried to call her names and express his frustration, but it hasn’t changed the situation. He’s still waiting for her to come back to him, as he sings, “I’m still waiting for your heart.”

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