35 Best Songs About Regret, Guilt & Mistakes

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Written By Will Fenton

Founder of MidderMusic. From numerous bands to stints working in music shops, read more about me on the 'Here's My Story' page!

Is regret a bad thing? 

Probably not. 

But just like any emotion, it isn’t easy to deal with. 

It is a slow process of introspection when you finally realize that you should have probably handled a past situation better.  

Intrinsically though, everybody knows how regret can affect our mood, making life miserable by making us appear like losers. 

If you’ve recently found yourself dwelling on bad memories, you will probably need the perfect playlist to change your mood. 

And our guide is based on just that. 

Here are the 35 best songs about regret to show you that mistakes are part of life, and you will always get a second chance, no matter how dark it appears. 

1. “Sorry” by Justin Bieber

Justin Bieber’s passionate narration in his 2015 dancehall pop song kicks off our list of the best songs about mistakes. 

We may never know what Justin might have done to regret it so much, but the track gets him apologizing to a woman in their romantic relationship. 

We don’t know if his apology saves or worsens the situation.

But we hope the addressee found it worthy in her heart to forgive him because his regret song is earnest. 

2. “Father and Son” by Cat Stevens

This song displays a spectacular fallout between a father and a son. 

While the father can’t seem to grasp his son’s desire to make a fresh start, the young man isn’t helping himself either by failing to explain his intentions.

In the end, there’s a catastrophic fallout between the pair. 

Stevens was inspired to write this song from his experiences with his father, rejecting the path laid down by the old man in favor of pursuing his destiny. 

3. “Hello” by Adele

Adele’s ‘Hello’ is a mellow 2015 song that’s interpreted differently by many people. 

But according to the singer, the triumphant track reflects her past life. 

With beautiful, moody, yet powerful lyrics, Adele can’t stop wondering if she might have lost a couple of friends now that she is famous. 

She mentions friends, ex-boyfriends, and her late grandfather, perhaps regretting how things turned out after rising to stardom status. 

4. “Sorry Seems To Be The Hardest Word” by Elton John 

A shot at forgiveness is all it takes to implore a loved one to forgive you for any wrongdoing. 

But in Elton John’s 1976 mournful ballad, the five-letter word seems to be the most difficult to say.

The singer wishes he could salvage his failing relationship, but deep down, he knows it is just as good as dead. 

5. “Hard To Say I’m Sorry” by Chicago

Hard To Say I’m Sorry’ catalyzed Chicago’s resurgence in the music industry, peaking at #1 in the US. 

Lyrically, the song is about trying to salvage a dying relationship. 

It is one of those regret songs where the actual apology doesn’t quite work out. 

And as predictable as most Chicago songs, ‘Hard To Say I’m Sorry’ raised the bar, lyrically satisfying to the music critics.  

6. “Apologize” by Timbaland Ft. OneRepublic 

Another shot at an apology? 

Timbaland and OneRepublic’s ‘Too Late To Apologize’ describes the pain of being in a dying relationship. 

It’s about two lovebirds whose relationship has stood many obstacles. 

But for some reason, it can no longer continue, creating a genuine desire to move on. 

It was a sensational international hit, topping the charts in Italy, Holland, New Zealand, Switzerland, and Australia, among other countries. 

7. “I Still Believe In You” by Vince Gill

Vince Gill wrote this song to apologize to his lover for not spending much time with her. 

He’s on the verge of losing his romantic partner and almost regrets his decision to prioritize other things instead of her. 

And having messed up before, he’s now ready to make up for it by showing more commitment to their relationship. 

8. “Sorry” by Ciara

Looks like some apology songs come with hidden regrets. 

In this 2012 R&B classic, Ciara is candid about her past relationship. 

She misses her ex-boyfriend and still loves him dearly. 

The Atlanta songstress pours her heart out in this song, oozing emotional lyrics that will make you want to shed a tear. 

9. “Forgive Me” by Evanescence 

This is a simple song about forgiveness. 

The narrator talks about his mistakes, regretting the terrible things he had said to the addressee. 

He’s ready to apologize in this regret song, having realized his mistakes. 

10. “Knowing Me, Knowing You” by ABBA

‘Knowing Me, Knowing You’ marked an important turning point in ABBA’s music career. 

It is one of the most powerful songs written by the group, referencing the high-profile divorces involving some of the band’s most prominent members. 

11. “Regret” by New Order 

It isn’t easy being in the limelight. 

And for many artists, some of the toughest moments in life are those spent entertaining their fans. 

That’s the case with New Order’s ‘Regret’ song, describing the painful life of celebrities. 

‘Regret’ was New Order’s top charting song in the UK, blending the amazing lyrics with spectacular vocals to become one of the best singles about regret. 

12. “I Could Have Lied” by Red Hot Chili Peppers

Anthony Kiedis, one of the leading members of the Red Hot Chili Peppers band, wrote this song as a response to rejection. 

His girlfriend had just dumped him and he was looking for solace in some soothing music. 

The track is a mere regret song, with Anthony conceding that he should probably have lied to save himself the pain of getting dumped. 

13. “Jealous Guy” by John Lennon

John Lennon’s candid love song is probably referring to himself. 

Lennon has at some point described himself as a “jealous, possessive guy,” which perhaps explains his lyrics in this 1971 soft rock.

‘Jealous Guy’ reveals Lennon’s insecurities, going as far as hurting his loved one and then coming back to apologize. 

14. “Against All Odds” by Phil Collins 

‘Against All Odds’ is a romantic power ballad of the 80s. 

It is a personal song written from an emotional perspective about Phil Collin’s estranged lover. 

The narration has the singer imploring her ex-wife to give him another chance. 

Today, the song has found a new meaning in different contexts and could be an uplifting tune when battling tough situations. 

15. “Someone You Loved” by Lewis Capaldi

Lewis Capaldi’s ‘Someone You Loved’ is a lyrical description of investing your emotion in someone but ending up disappointed. 

It is a sad song symbolizing the end of a relationship with someone who cared for you, loved you unconditionally, and supported you. 

According to Capaldi, the person in question is his grandmother. 

16. “Hurt” by Johnny Cash

This song is based on self-destructive behaviors like drug addiction. 

Cash’s narration is the perfect regret song, describing his bad life. 

The singer realizes that he might have prioritized the wrong things all along, but with little time to recreate his life, it appears he’ll have to live with the regrets. 

17. “So Sorry” by Feist

In this 2007 pop song, Feist reckons that sometimes, all you have to do is say the two words instead of fighting in a relationship or letting go. 

And we can’t think of a more powerful act in a romantic relationship than apologizing. 

18. “Fire And Rain” by James Taylor 

James Taylor was barely 21 when he wrote ‘Fire And Rain’ in 1968. 

It highlights his most memorable moments in life, including the highs and lows. 

The track has three verses about his friend’s suicide, his heroin addiction, and a mental hospital. 

The candid confession shows that James Taylor is only human after all, struggling with the typical issues everybody was probably battling at the time. 

19. “Please Remember Me” by Tim McGraw 

It’s difficult to smile when parting ways with a loved one. 

But Tim McGraw shows us a different approach in his heartache song, where he’s wishing his ex-lover good fortune as they part ways. 

The narration is about a man separating from his lover, with a memorable chorus where Tim reassures her that she’ll find better love. 

20. “If I Could Turn Back Time” by Cher

We take a lot of things in life for granted until we can no longer reclaim them. 

And in this powerful 1989 song, Cher’s only wish is to get a second chance. 

It’s obvious that her hurtful past is fast catching up with her, and she’s remorseful of her actions in a previous relationship.

At this point, she doesn’t want to appear helpless but only hopes that she can reverse the time and make everything right. 

21. “Butterfly” by Weezer 

Some relationships were never meant to be. 

But some romantic stories are even more painful. 

‘Butterfly’ by Weezer is a song about taking advantage of someone’s innocence and using them for your selfish gain. 

The narrator is merely satisfying his bodily lust while the addressee is patiently waiting for a long-term commitment. 

22. “Somebody That I Used To Know” by Gotye 

Gotye’s indie song is about the confusion after a messy breakup. 

While the breakup isn’t as nasty, the singer admits they hurt each other in more ways than they may have wanted. 

You will probably have different ways to handle breakups in life. 

But how do you handle an ex-lover after they become ‘someone you used to know?’ 

Perhaps Gotye has an answer.

23. “Back To December” by Taylor Swift

You read that right. 

Taylor Swift is finally apologizing to a former lover using actual lyrics. 

Some will say that Swift tends to play the victim in most of her songs. 

But anyone who’s listened to this track will probably disagree. 

Here, the American songwriter is apologizing to an ex-lover in one of her many romance stories. 

She uses ‘going back to December’ metaphorically to reference the day they ended their romantic affair. 

24. “When I Was Your Man” by Bruno Mars

‘When I Was Your Man’ is an emotional track describing Bruno Mars’ pain and regret for taking his lover for granted. 

Mars sings it brilliantly, conceding that he was a fool for letting an amazing lover go away. 

It is not the memory that hurts. 

But rather the regret of losing someone who cared so much for him. 

Talk of appreciating something when it’s gone. 

25. “All Apologies” by Nirvana 

Everybody talks about Nirvana’s ‘Smells Like Teen Spirit’ and ‘Come As You Are.’ 

But there’s one more song that stood out in the 90s era because of its almost prophetic element. 

‘All Apologies’ was a bit like a premonition, foreshadowing Kurt Cobain’s death a year later by suicide. 

It could be just us. 

But honestly, we can’t be the only ones relating this song to the mournful context of Cobain’s suicide. 

26. “Regret” by LeToya Luckett

‘Regret’ is a modern R&B classic where LeToya Luckett pours her heart out to her ex-lover. 

It is the third single from the singer’s ‘Lady Love’ album, where she describes how she will miss her ex. 

Lyrically, this is one of those remorseful songs where the narrator deeply regrets separating from her lover. 

27. “Sorry For The Stupid Things” by Babyface

You can tell the message in this track from the title alone. 

It is a plainly written song about regret and guilt, with Babyface owning up to his past mistakes without beating around the bush.  

28. “Tears In Heaven” by Eric Clapton

You better get your tissues out before listening to Eric Clapton’s emotional song because the lyrics will surely take you to a dark place. 

‘Tears In Heaven’ is based on a true life story, describing the tragic death of Conor, Eric’s son, who sadly passed on at only 4 years. 

Clapton oozes emotions in the song, asking his son if he would still recognize him in heaven. 

The devastating lyrics continue throughout the song, with Clapton presumably asking his son for forgiveness. 

29. “Supermarket Flowers” by Ed Sheeran

Ed Sheeran’s ‘Supermarket Flowers’ is a bit like the aforementioned ‘Tears In Heaven’ and will make you teary every time you listen to it. 

Everybody talks about strength in tough times, but not even one of the best pop artists in history could hold back his tears at the painful death of his grandmother. 

The singer describes it as ‘the most special song on the record for me,’ and you can’t dispute that, considering how tough it can be to bear the loss of a loved one. 

30. “Waves” by Dean Lewis

What should someone do when life’s excitement fades away? 

For some, that means sinking into depression or self-destructive behavior like an addiction. 

But for Dean Lewis, that’s a chance to sum up his feelings in another masterpiece. 

Nobody knows if Lewis is already feeling depressed, but the track perfectly summarizes the loneliness when life’s enthusiasm eludes you. 

While the lyrics appear to describe relationships, Lewis has reiterated that the track talks about how life’s excitement dwindles with increasing age. 

31. “Stay With Me” by Sam Smith

It isn’t difficult to see that Sam Smith is talking about regret in this sentimental track.

The narration is based on a broken soul looking for someone to fill the voids in his life. 

He opts for a one-night stand to ease his loneliness, but he genuinely understands that this is not true love. 

32. “when the party’s over” by Billie Eilish 

Billie Eilish isn’t a stranger to the theme of regret and heartbreak in most of her songs. 

And in one of his best singles about love, she uses party metaphorically to represent the reckless decisions someone makes in her love life. 

Billie kills the lyrics with her unique style, living up to the natural talent she’s always possessed.

33. “Cats in the Cradle” by Harry Chapin

‘Cats In The Cradle’ is one of the most relatable songs about missed opportunities. 

It highlights a father-and-son relationship where the former is always busy with his career.

The powerful lyrics serve as a warning to many people, highlighting the need to share those little moments with your loved ones. 

Listen to this song if you are ever tempted to prioritize your career over family.

34. “Please Forgive Me” by Bryan Adams

Bryan Adams uses his lyrical prowess to ask for forgiveness from a lady he’s madly in love with. 

The song is not mere forgiveness, as many people assume. But rather, a formal request to the addressee for loving her so much. 

If you’ve ever loved someone so much you couldn’t imagine your life without them, the lyrics will make perfect sense. 

But whether Bryan had to go to such lengths to express his love is another story. 

35. “Everybody Makes Mistakes” by Hannah Montana

Closing our list of the best songs about regretting hurting someone is Hannah Montana’s confession that we all make mistakes. 

In the track, she affirms that everybody has those days when things just don’t go quite right. 

The lyrical interpretation means that no one in the world is perfect. 

And what matters is how fast you get yourself back up, learn from your mistakes, and move on. 

Quite simply, Montana wants everyone to know that there’s no point in getting caught up in bad memories when we all know no one has it all figured out. 

Songs About Regret – Final Thoughts

Songs about guilt hit differently when you are going through the same situation. 

And while the feeling is sometimes overwhelming, you can relieve the pain by listening to other people with similar stories to tell. 

Creating the perfect playlist can help you overcome the burden of regret and help you recreate your life, even from scratch. 

All the regretting songs on our list prove that not even the most famous individuals have it all figured out. 

And you can always find solace in their songs about regret and guilt. 

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