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21 Best Songs About Guilt & Mistakes

The guiltiest, most soul-stirring anthems of all time.



Best Songs About Guilt

The best songs about guilt reflect this powerful emotion in all its aspects, covering everything from the regret we feel for losing a lover to the things we should have said before a relative dies.

It’s a universal feeling that’s been the subject of music from all types of genres, from classic rock ballads to modern-day pop song hits.

Continue reading for a complete breakdown of the best songs exploring guilt and regret in all its forms from the leading singers and bands around.


The 21 Best Songs About Guilt & Mistakes

We’ve scoured through the music archives to ensure this list covers the subject of guilt from all angles and points of view.

This list includes everything from obscure folk-rock songs to mainstream chart-topping pop songs from international stars.

Read on, and we’ll run through our playlist of the best songs about guilt and mistakes:


21. “Perfect” – Simple Plan

Simple Plan takes the concept of guilt and delivers an ironic song called “Perfect,” released in 2002.

“I’m sorry I can’t be perfect,” the lyrics read, continuing, “Now it’s just too late and we can’t go back.”

It’s an emo indie rock classic from the Canadian band’s album No Pads, No Helmets…Just Balls, which earned them an award for Favorite Canadian Group.


20. “Hard To Say I’m Sorry” – Chicago

Chicago made their comeback into the music industry in 1982 with the hit song “Hard To Say I’m Sorry,” which reached number one on the American charts.

This is a song about the regret that comes from a guilty conscience after fighting with a romantic partner and breaking up.

It was remastered in 2009, elevating the already excellent production values of the original version to another level.


19. “I Could Have Lied” – Red Hot Chili Peppers

Anthony Kiedis wrote the song “I Could Have Lied” as a response to rejection in his life after his girlfriend had recently ended their relationship.

It’s a relatable song for anyone who has been through a breakup, with lyrics revolving around how he should have lied to avoid being dumped.

Red Hot Chili Peppers have released many great tracks, including one of the best songs about death, “Brendan’s Death Song,” dedicated to the passing of Brendan Mullen.


18. “Never Be Like You” – Flume ft. Kai

Alternative R&B/future bass song “Never Be Like You” is one of the more powerful songs about guilt that deals with reflecting on past mistakes.

The lyrics read, “I’m only human, can’t you see? I made, I made a mistake please just look me in my face.”

Flume and Kai released the track on the album One in a Million: A Future Classic Compilation in 2016 to critical and commercial acclaim.


17. “Sorry” – Justin Bieber

Sometimes “Sorry” is the only word needed to absolve a person of their feelings of guilt, as Justin Bieber understands in his simple pop song.

It’s a passionately narrated song that sees Bieber apologizing for the wrongs he committed to a previous lover.

Bieber delivers the emotional lyrics in style, and “Sorry” is perhaps one of the most famous songs about guilt ever recorded. 


16. “Against All Odds” – Phil Collins

Phil Collins is no stranger to writing and singing emotional power ballads, and “Against All Odds” is no exception.

The lyrics see Collins seeking forgiveness from his ex-wife and pleading with her to give him another chance to fix their relationship.

Phil Collins has enjoyed a prolific career, which includes one of the best songs about heaven, “Something Happened On The Way To Heaven.”


15. “Was I Right Or Wrong” – Lynyrd Skynyrd

One of the main issues with feeling guilty is knowing whether you were actually in the wrong, as this great song by Lynyrd Skynyrd demonstrates.

“Was I Right Or Wrong” poses the question without providing any clear answers, and it’s this ambiguity that makes it so relatable.

It’s a classic rock track from the 1970s and was featured on the band’s second studio album Second Helping.


14. “Jealous Guy” – John Lennon

John Lennon’s songs covered a broad spectrum of themes and concepts, with love and guilt at the fore in the song “Jealous Guy.”

It’s a soft rock ballad with distinct vocals that reveals his insecurities and how he realizes the need to apologize to his loved one.

Released in 1971, it offered fans of Lennon an insight into his relationship with Yoko Ono and how he would behave irrationally in her presence.


13. “Whatcha Say” – Jason Derulo

Jason Derulo merges hip-hop with R&B to great effect in his excellent song “Whatcha Say,” which was featured on the album of the same name.

The lyrics have a confessional aspect, “I was so wrong for so long only tryin’ to please myself.”

“Whatcha Say” was released in 2009 at the beginning of Derulo’s career, and he has since sold over 200 million singles worldwide.


12. “Hurt” – Johnny Cash

Just as Justin Bieber kept his song title nice and simple, so too does Johnny Cash cut to the chase with his song “Hurt.”

It’s a song about self-destruction and drug addiction fueled by feelings of guilt and shame and the downward spiral of abuse.

Johnny Cash’s version is a cover of the 1994 track of the same name written by Trent Reznor and performed by Nine Inch Nails.


11. “Tears In Heaven” – Eric Clapton

Eric Clapton weighs in on the topic of guilt with “Tears in Heaven,” a genuinely heartbreaking song about any parent’s worst nightmare, the tragic death of his son.

Clapton’s son Conor was just four years old when he passed away, and the song is appropriately melancholic and deeply moving.

It’s another exceptional entry in Clapton’s discography, earning him 17 Grammy Award wins and 37 nominations.


10. “Supermarket Flowers” – Ed Sheeran

Ed Sheeran delivers another tear-jerker song about guilt with “Supermarket Flowers,” which he has claimed is the most special song of his career.

It’s another moving piece of music about the death of a loved one, with Sheeran singing about “a heart that [is] broke is a heart that [has] been loved.”

These feelings prompt a sense of guilt that Sheeran struggles to come to terms with as he laments the passing of his dear grandmother.


9. “Always On My Mind” – Willie Nelson

Gwen McCrae originally wrote the song “Always on My Mind” in the 1970s, but for our money, it’s the Willie Nelson version you need to hear.

It’s a song deeply embedded in guilt and regret, questioning whether they gave their partner enough love and why they left them.

It’s a stirring and emotional country ballad that anyone who has been in a failing relationship can find something to agree with in the lyrics.


8. “I’ve Changed My Plea To Guilty” – Morrissey

Morrissey has made a career by writing moody and meaningful songs with deep lyrics, and “I’ve Changed My Plea To Guilty” is no exception.

It’s a superbly performed piece of music in which the singer regrets that he doesn’t have anyone to love.

It won’t surprise anyone familiar with Morrissey’s music to hear that he wrote one of the best songs about anxiety and continues to mine these emotions with his recent music.


7. Guiltiness” – Bob Marley ft. The Lost Boyz & Mr. Cheeks

Bob Marley opted to broaden his net and collaborate with The Lost Boyz and Mr. Cheeks for his seminal song, “Guiltiness.”

It’s a song geared toward highlighting injustice and corruption worldwide, with lyrics talking about big fish always trying to eat the little fish.

The original version of “Guiltiness” was featured on the Marley album Exodus, without the involvement of The Lost Boyz and Mr. Cheeks.


6. I Threw It All Away” – Bob Dylan

From Bob Marley to Bob Dylan for another excellent song that captures the essential qualities of guilt, “I Threw It All Away.”

Dylan’s instantly recognizable vocals sing about how he “once I had mountains in the palm of my hand,” but now he’s all alone.

A prolific songwriter with dozens of hits to his name, Dylan is also responsible for one of the best songs of all time, “Like A Rolling Stone.”


5. “Back To December” – Taylor Swift

Taylor Swift took the opportunity to apologize for her regrettable behavior in the form of a song, “Back To December.”

It’s another of her romance story songs that she uses to say sorry for the way she treated a former lover and uses the month of December as a reference to when their affair ended.

It’s also a catchy pop song that fits in perfectly with the singer’s discography, which includes one of the best karaoke songs of all time, “Love Story.”


4. “Hello” – Adele

Adele’s mellow entry to great songs exploring the concept of guilt, “Hello,” can be interpreted in many different ways depending on your life experiences.

The lyrics and her vocal prowess make “Hello” a moving experience to listen to as she laments her previous friends, lovers, and deceased family members.

Adele released the track on her studio album 25, another massive hit for the singer, selling millions of copies worldwide.


3. “The Dream’s In The Ditch” – Deer Tick

Hugely popular indie folk music band Deer Tick released “The Dream’s In The Ditch” in 2013 to critical and commercial acclaim.

It’s not exactly a positive song, which is what you’d expect from the topic of disillusionment, regret, and feeling guilty.

Fittingly, it was included on their equally downbeat album from 2013 titled Negativity, which led to the band taking a break from the studio to work on other projects.


2. “Regret” – New Order 

Guilt and regret often go hand in hand, as New Order explored in their song “Regret,” which was a chart-topping hit for the band in the UK.

This song about guilt is all about the life of being a celebrity and how it separates a person from the ordinary world in often painful ways.

It’s a wonderful blend of deep and meaningful lyrics with incredible vocals and clever instrumentation from one of the era’s best bands.


1. “The One That Got Away” – Katy Perry

Katy Perry is among the most successful pop singers of her generation, with multiple number-one hits on the Billboard Hot 100 charts throughout her career.

“The One That Got Away,” released in 2011, is another song about guilt and regret for letting a loved one slip through her fingers despite all the signs of being a soul mate.

It hints at the problem everyone has with regret and how their imagination takes over, and they imagine an idealized version of what could have been that might not have been the reality.



We hope you’ve enjoyed this selection of the best songs about guilt and found something you can relate to from your own experiences in life and relationships.

Whether it’s feeling guilty for losing a loved one or a broken relationship, it’s a powerful feeling that has led to some emotionally-charged music.

Guilt has been explored in many popular songs, and we can expect it to continue to feature in the discographies of the hottest pop stars and bands worldwide.

What great songs capture the essence of guilt you’ve listened to? Leave a comment below.

Andy has been producing music since the early days of Cubase and spent much of the 2000s mixing house and techno with his trusty Technics 1200s. Fast forward two decades, you'll find him in his home studio experimenting with the latest music production software, tinkering with Ableton plug-ins, and occasionally trying (and failing) to complete Cuphead for the hundredth time.