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23 Best Songs about Regret, Guilt, and Mistakes

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This list will include 23 of the best songs about regret, guilt, and mistakes. Songs about these topics come from a variety of different genres. Artists who make rock, pop, jazz, classical, blues, soul, country, and even rap music have these regretful themes prominent in their music.

Regret and guilt are universal emotions. Even if people do not like to admit it, all individuals make mistakes sometimes. For this reason, songs about guilt, regret, and mistakes can be universally relatable for listeners. Listeners who are trying to process similar emotions may feel less alone while listening.

1. “Damn Your Eyes” – Etta James

Etta James’ emotional song “Damn Your Eyes” was released as a part of the album ‘Seven Year Itch‘ in the year 1988. The song has also been covered by a variety of artists including Alex Clare, who covered the song in the year 2011 and Joe Bonamassa and Beth Hart, who covered it in the year 2018. James’ voice, however, is most well known for its emotional quality.

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2. “The Dream’s in the Ditch” – Deer Tick

“The Dream’s in the Ditch” was released by popular indie folk act Deer Tick in the year 2013 as a part of the album ‘Negativity.’ As the album’s title might imply, the song is not a positive one. It describes feelings of regret and serious disillusionment. Feelings of disillusionment often come alongside feelings of regret and guilt, so this makes sense.

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3. “Supermarket Flowers” – Ed Sheeran

“Supermarket Flowers” is a heartbreaking song by popular vocalist Ed Sheeran. He describes feelings of loss and despair throughout the track. He sings that “a heart that [is] broke is a heart that [has] been loved.” He simultaneously exhibits his feelings of guilt and his efforts to let go of those feelings of guilt at the same time. He does not like seeing the objects around him that make him feel guilty or sad, and so he cleans them up.

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4. “Tears in Heaven” – Eric Clapton

“Tears in Heaven” was written by Eric Clapton about the loss of his four and a half year old son who fell out of a 53rd story apartment window. The soft rock song was co-written by artist Will Jennings. Unresolved and unexpressed emotions will always be associated with feelings of regret and guilt. What happened to Clapton’s son was a tragic mistake. Even though it was not his fault, the hurt is still very real.

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5. “Hard to Say I’m Sorry” – Chicago

The song “Hard to Say I’m Sorry” by Chicago is about regrets and guilt of the romantic variety. Lovers often feel regret and guilt after fights or breakups. Mistakes also happen within relationships. The apologetic lyrics of this song could be relatable to anyone who has been in a romantic relationship before. The song ends with a promise to do better, as many songs about mistakes do. Whether or not the target accepted that apology, audiences will never know.

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6. “Please Forgive Me” – Bryan Adams

The title of the song “Please Forgive Me” by Bryan Adams makes its message evident before you even listen to it. Romantic regrets and memories can make for especially painful songwriting material. Listening to the song, you cannot help but wonder how the recipient took it. The pained emotion of the song might make it hard to deny, especially if it was written and performed with a specific subject in mind.

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7. “Hurt” – Johnny Cash

The song “Hurt” originally written and recorded by Trent Reznor and his band Nine Inch Nails in the year 1994. Both versions of the song are devastatingly emotional and heartfelt. This song is one of the songs most commonly associated with feelings of remorse and regret. Unfortunately, it is also a very relatable song for many people who struggle with relationships, depression, or life in general.

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8. “Sorry” – Justin Bieber

Even upbeat pop songs can carry heartfelt emotional messages about regret and guilt. Do not let the fun and airy music deceive you. The lyrics to “Sorry” by Justin Bieber are sadder than you might have thought when first listening to it. Even though he does not use a pained vocal delivery, you can still tell by the lyrics that the song is about regret, guilt, and mistakes.

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9. “Fire and Rain” – James Taylor

“Fire and Rain” was released by James Taylor in the year 1970 as a part of the album ‘Sweet Baby James.’ In the song’s painful lyrics, James Taylor even calls out to Jesus for help dealing with his feelings of regret and guilt. If you are looking for a classic oldies song about regret, guilt, or mistakes, look no further than this timeless track.

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10. “Please Remember Me” – Tim McGraw

Country singer-songwriters seem to love performing songs about mistakes, guilt, and regrets. They often lament lost lovers and childhood memories while crying out over sorrowful acoustic guitar chords. Tim McGraw is no outlier to this rule. The hit country artist is especially known for his emotional lyrics. With these factors in mind, it is no surprise that “Please Remember Me” is included on this list.

11. “I Still Believe in You” – Vince Gill

“I Still Believe in You” was recorded and co-written by US based country music recording artist Vince Gill in the year 1992. The song was released on June 29 of that year. In the song Vince Gill expresses regret about losing track of himself. He apologizes for taking so long to realize the regret that he feels and begs for a second chance. This is something people often do when they feel that they have made mistakes. That does not mean that the apology is always accepted.

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12. “The Living Years” – Mike + The Mechanics

Songs about regret, guilt, and mistakes can even become award winning hits. After this song was released in 1988, it was nominated for four separate Grammy Awards. This song tells a story of generational and familial guilt. Feelings of regret associated with family relationships can be just as painful as, if not more painful than those feelings of regret that go along with romantic relationships. This song is one of the better storytelling songs out there, for sure.

13. “Forgive Me” – Evanescence

Evanescence’s lead vocalist and pianist Amy Lee is well known for her haunting, emotional vocal delivery and songwriting skills. She is able to convey pain, regret, loss, and longing all with the tone of her voice. The 2004 song “Forgive Me” tells a heartbreaking yet pleading tale of remorse, regret, bargaining, and apology. These emotions can be extremely painful to deal with but it often helps listeners to know that they are not alone in feeling them.

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14. “Waves” – Dean Lewis

“Waves” was released by singer and songwriter Dean Lewis in the year 2016. The song was well received. It received multiple different ARIA award nominations, including Song of the Year, Best Video, Best Pop Release, and Breakthrough Artist. In this song, Dean Lewis sings about the regrets associated with growing up and no longer being able to live free as a child anymore.

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15. “Sorry For the Stupid Things” – Babyface

The title of this song by Babyface makes it pretty clear that the song will be about mistakes, regret, and guilt. He does not beat around the bush with metaphors when making his apology; it is in the title of the song! This song was released in the year 2005 as a part of the album ‘Grown and Sexy.’ The song also features hit recording artist Keyshia Cole. We personally love songs with figurative language, as they often keep the storytelling very interesting!

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16. “Find ‘Em Fool ‘Em and Forget ‘Em” – Anderson East

In this song, Anderson East sings about the regrets associated with romantic heartbreak. Often all of the trust and love put into a relationship starts to look like nothing but a mistake by the end. In the heat of his heartbreak, he even wishes to go back in time so that he can take all of his love and affection back. In a twisted way, he regrets not following his father’s negative example as a womanizer because of the hurt he has endured.

17. “All Apologies” – Nirvana

Many songs about regret, guilt, and mistakes are also about apologies and saying sorry. This grunge song released by Nirvana in the 1990s features some repetitive and seemingly nonsense lyrics, but the overwhelming theme of the song is regret and guilt. Lead vocalist and guitarist Kurt Cobain even goes as far as to sing “everything is my fault…I’ll take all the blame.”

18. “Sorry” – Madonna

Madonna has released so many different songs over the course of her massive career that she has touched on nearly every subject possible. This song is addressed towards a partner who is feeling remorseful and guilty. Madonna is having no part of it. She sings that she does not want to hear sorry – in English, French, Japanese, or any other language. This song could easily be a diss track response to many of the other songs on this list.

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19. “Someone You Loved” – Lewis Capaldi

“Someone You Loved” was released in the year 2018 as a part of the Lewis Capaldi album ‘Breach.’ This emotionally charged track conveys feelings of despair, loss, regret, and overall loneliness. The song was written in part by Capaldi, along with the assistance of Benjamin Kohn, Peter Kelleher, Samuel Roman, and Tom Barnes. They are all credited as songwriters for this track as well.

20. “Butterfly” – Weezer

Weezer is a band far more commonly known for their quirky and upbeat alternative radio hits than for their tracks about regret, guilt, or mistakes. This metaphorical and apologetic song tells the story of a young child who locked a butterfly away in a jar, only to find it dead the next day. This might be a metaphor for smothering or trapping a romantic partner who should have been left free. It might just be a sad memory from the songwriter’s childhood. What is most important is that the lyrics convey a difficult, but relatable feeling to the listener.

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21. “Stay With Me” – Sam Smith

Even if you did not speak the English language at all, you would be able to tell from listening to “Stay With Me” that it is a song about regret. Sam Smith’s emotional vocal delivery makes it easy to feel the pain that he feels. The overall message of the song is similar to others on this list, yet the song is still massively popular. As years go on, music fans will always crave new songs about this relatable type of subject matter.

22. “Everybody Makes Mistakes” – Hannah Montana

Songs about mistakes do not always have to be sad. They also do not always have to be for adults. The song “Everybody Makes Mistakes” by Hannah Montana addresses the topic of mistake making in a different way than any of the other songs on this list. In this upbeat pop song, the Miley Cyrus alter ego and daughter of country star Billy Ray Cyrus tells listeners that making mistakes is a normal part of life that they should not feel bad about.

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

Britney Spears may have known that she had made some mistakes when she made and released the song “Oops!…I Did It Again” but she certainly did not feel guilty about it. She acknowledges that she is “not that innocent” and cannot always be trusted romantically. At least she is able to be honest about that quality in herself. She also was only a teenager when the song was released and has grown since then.

If you want to get more in touch with your emotions, you may want to listen to one of these songs. If you are going through a difficult time, you may also want to listen to them. Knowing that other people have felt those same emotions too can be helpful. Even if it does not help, you still might find yourself cheered up by dancing or singing along.

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