We have all done something we regret or feel guilty about in our lives. It doesn’t matter if it seems insignificant at the time or if it’s catastrophic. You should feel remorse for your actions. Almost all humans have experienced this, which is why so many songs about regret and guilt have been written over the years.
The best thing you can do is move on with your life and make amends with yourself or anybody harmed by your actions. So, how do you do that? I have always found that it is helpful to apologize and drown your sorrows in music. Here is an awesome list of songs that can help you if you have regrets or if you’re feeling guilty.
1. Hurt by Johnny Cash
| Genre | Country |
| Year Released | 2002 |
| Album | American IV: The Man Comes Around |
It’s not very often that you hear a cover song that is better than the original, but that’s exactly what Johnny Cash did when he covered the song “Hurt” by the industrial rock group Nine Inch Nails on his 2002 album “American IV: The Man Comes Around.” Cash took this chilling song and made it his own, turning it into a prophecy of his death, in which he had come to regret many of the things that he had done throughout his long life. Trent Reznor has even said that he thinks this version is better than his.
2. Before You Go by Lewis Capaldi
| Genre | Pop |
| Year Released | 2019 |
| Album | Divinely Inspired To a Hellish Extent |
With “Before you Go,” Lewis Capaldi breaks my heart every time I hear it. Taken from his 2019 record “Divinely Inspired To a Hellish Extent,” Capaldi is being unceremoniously dumped by his partner. In a voice that can only be described as painstakingly beautiful, he asks if there is anything that he could have done that would have made her life and the relationship better. It’s not hard to hear the guilt and regret in his voice. This song is one of a few that has the power to make me cry every time I hear it.
3. Alive by Pearl’s Jam
| Genre | Grunge |
| Year Released | 1991 |
| Album | Ten |
When Eddie Vedder and the rest of Pearl Jam released the album “Ten” in 1991, little did they know that the song “Alive” would become a smash hit? The song is about a mother who has lied to her son for many years about who his real father is. In reality, a child’s father died when he was approximately 13 years old. The boy regrets that he never had the chance to get to know his real father, and his mother regrets deceiving him for all those years. However, she’s still alive, and that’s all that matters to her.
4. Empty by Juice WRLD
| Genre | Rap, Hip Hop |
| Year Released | 2019 |
| Album | Death Race For Love |
Every time I think about the rapper Juice WRLD, I am deeply saddened that we lost such a great talent in the prime of his life. Sadly, Juice suffered from a deadly combination of depression and chemical dependency. Fortunately, he was able to give us amazing tracks like “Empty” from his 2019 album “Death Race For Love” before he passed away. This song talks about his problem with drugs and alcohol and expresses regret for becoming addicted to these substances. Unfortunately, his cries for help were heard a little too late. If only we had listened.
5. I Miss You by Blink-182
| Genre | Pop Punk |
| Year Released | 2003 |
| Album | Blink-182 |
Known primarily for their pop-punk sound and carefree attitude, Blink-182 is possibly the last band you would expect to see release a song about regret or guilt. However, that’s exactly what the song “I Miss You” from their self-titled album is all about. It’s a song about one of the most tragic experiences in life, which is losing a loved one. Unfortunately, Mark Hoppus feels like the reason that this person is dead is all his fault, and it pains him greatly as heard when he sings, “Will you come home and stop this pain tonight?”
6. Please Remember Me by Tim McGraw
| Genre | Country |
| Year Released | 1999 |
| Album | A Place in the Sun |
Country music is full of artists who make songs about regret and guilt for many different things. Tim McGraw is no stranger to this concept either. Coming from the 1999 record “A Place in the Sun,” the song “Please Remember Me” is about a guy and a girl who was involved in a relationship that didn’t last. Although Tim McGraw regrets that the relationship had to come to an end, he is not bitter about what happened. Instead, he wishes his ex well on her journey and asks that she remember him and their good times.
7. The Living Years by Mike and The Mechanics
| Genre | Pop |
| Year Released | 1988 |
| Album | Living Years |
In 1988, Mike and the Mechanics made a big splash with their hit single “The Living Years” from the album of the same name. Formed as a side project by Genesis guitarist Mike Rutherford, Mike and the Mechanics were not afraid to tackle the tough topics like seeing things from the perspective of an estranged son who has lost his father. Unfortunately, it took his father’s death to see how much the two of them had in common. Now, all the sun is left with is regret that he didn’t spend more time with his father.
8. Always On My Mind by Willie Nelson
| Genre | Country |
| Year Released | 1982 |
| Album | Always On My Mind |
Willie Nelson is considered to be country music royalty, and in 1982 he released what would become one of his biggest hits. Taken from the album of the same name, the song “Always On My Mind” became one of Willie Nelson’s signature songs and has been covered many times since then. The song expresses Willie’s guilt over not having treated his wife better and his regret that his actions caused her to leave him. After the relationship has ended, he wants her to know that despite his actions, she was always in his thoughts. If you’re looking for songs about regretting hurting someone, then this is one you’ll definitely want to listen to.
9. Interstate Love Song by Stone Temple Pilots
| Genre | Alternative Rock |
| Year Released | 1994 |
| Album | Purple |
Stone Temple Pilots have a talent for being able to paint a picture with words and music. Such is the case for the tune “Interstate Love Song” from their 1994 sophomore album “Purple.” Anybody familiar with Scott Weiland knows that he had an ongoing battle with substance abuse. He wrote this song from the perspective of his girlfriend and her ability to see through his lies about his heroin addiction. He has gone on record expressing that he regrets that his addiction broke them up and felt guilty about lying to her about it.
10. Somebody That I Used to Know by Gotye (Featuring Kimbra)
| Genre | Pop |
| Year Released | 2011 |
| Album | Making Mirrors |
Gotye made a splash in 2011 with his single “Somebody That I Used to Know” from the album “Making Mirrors.” While everybody was spinning the song, few people realized that Gotye drew from personal experiences while he was writing this song and has said that it is about the regret that you feel in the aftermath of a bad breakup. After the fighting is over, the relationship has ended and you are left with somebody that you feel like you don’t know anymore, and the guilt and regret you feel that the relationship ended.
11. Suicidal Thoughts by Notorious B.I.G
| Genre | Rap, Hip Hop |
| Year Released | 1994 |
| Album | Ready To Die |
The 1994 classic album “Ready To Die” by Notorious B.I.G is known throughout the hip-hop community as one of its best albums of all time, and the track “Suicidal Thoughts” is one reason why it is held in such high regard. In this song, Notorious B.I.G talks about how he doesn’t deserve to go to heaven when he does not because of all of the bad things he’s done. He knows that he could have done better for himself and his family, and he’s expressing regret and remorse before he crosses over.
12. Mama Tried by Merle Haggard
| Genre | Outlaw Country |
| Year Released | 1968 |
| Album | Killers Three |
Merle Haggard is the king of outlaw country, and that comes as no surprise with songs like “Mama Tried.” In this track from the 1968 record “Killers Three,” we see a side of Haggard that he doesn’t show very often. With lyrics like “And I turned 21 in prison, doing life without parole. No one could steer me right, but mama tried, mama tried,” we see Merle showing some regret for not listening to his mother when she tried to warn him about the life he was living. Unfortunately, he didn’t listen, but mama tried.
13. Like a Rolling Stone by Bob Dylan
| Genre | Indie, Folk |
| Year Released | 1965 |
| Album | Highway 61 Revisited |
As the story goes, “Like a Rolling Stone” was not a favorite of the record company and the producers from Bob Dylan’s 1965 all-time classic “Highway 61 Revisited.” Clever, Dylan fought for this song to be included on the album, and years later, Rolling Stone magazine crowned it the best song of all time. This song tells the tale of a woman who was once well off but now finds herself amongst the poor and downtrodden. As she looks back on her life, she regrets the decisions that she’s made to get to this point.
14. Damn Your Eyes by Etta James
| Genre | Pop |
| Year Released | 2017 |
| Album | Kurt Hugo Schneider 2017 |
Let me start by saying that I’m aware that this is the cover version of this song, not the original. Nonetheless, I prefer Ariana Grande’s version to the Kurt Schneider original. This song is about a woman who cheated on her boyfriend, and although she knows that he’s got someone better now, she regrets cheating on him and feels guilty about breaking his trust. You can hear the desperation in her voice when she sings, “I need to be the one who takes you home one more time. I promise after that, I’ll let you go.”
16. Amoreena by Elton John
| Genre | Classic Rock, Pop |
| Year Released | 1970 |
| Album | Tumbleweed Connection |
When Elton John opens this song with the lyrics “Just lately, I’ve been thinking, how much I miss my lady,” we immediately know that “Amoreena” is going to be a salon about how he regrets losing the love of his life. In this song from his 1970 record “Tumbleweed Connection,” it’s apparent that he doesn’t have any ill will towards her for any hard feelings about the relationship, speaking highly complimentary of his ex. However, Elton John has some regrets that the relationship he once treasured had to come to an end.
17. Bleeding Me by Metallica
| Genre | Heavy Metal |
| Year Released | 1996 |
| Album | Load |
This is one of the most introspective and insightful songs written by the heavy metal titans known as Metallica. In the 1996 album “Load,” the song “Bleeding Me” is about a person suffering from choices he has made throughout his life. While he regrets the choices he’s made, he knows they were his choices to make, and now he must suffer the consequences of his actions, as evident in the line “This thorn in my side is from the tree I planted.” At least he’s self-aware. This is by far one of my favorite songs about regret.
18. Hard For Me To Say I’m Sorry by Chicago
| Genre | Soft Rock |
| Year Released | 1982 |
| Album | Chicago 16 |
Back in 1982, the band Chicago released a record called “Chicago 16” that would have quite possibly been the most popular apology song of all time. That track was called “Hard For Me To Say I’m Sorry” and was the go-to song for any guy who realized that he messed up and wanted to apologize to his partner. Peter Cetera could bring even the toughest guy to tears when he belted out, “After all that you’ve been through, I will make it up to you, I promise to.” Now that is an apology that’s hard to resist.
19. Reclamation by Lamb Of God
| Genre | Heavy Metal |
| Year Released | 2009 |
| Album | Wrath |
Lamb of God prides itself in being one of the most bone-crushing bands in heavy metal today, which is why it is rare to find a song from this act that expresses any kind of remorse or regret. Although, the track “Reclamation” from the 2009 album” Wrath” is an exception. In typical Lamb of God fashion, they express regret and guilt for humanity’s penchant for destroying the environment in the name of progress and monetary gain. Lead singer Randall Blythe warns that one day we will regret our actions, but it will be too late.
20. When the Party’s Over by Billie Eilish
| Genre | Indie Pop |
| Year Released | 2010 |
| Album | When We All Fall Asleep, Where Do We Go?” |
I’ll start this by saying that Billie Eilish is certainly odd. There is no disputing that. However, she sure knows how to get her point across. Coming from her 2018 record ” When We All Fall Asleep, Where Do We Go?” Billie is expressing some regret for the things that she has done to her significant other throughout their relationship. She feels guilty for her actions and is warning her ex that getting back together would be a bad idea because she has not changed. At least she is mature and unselfish enough to realize this.
21. Ember City by Mastodon
| Genre | Progressive Metal |
| Year Released | 2014 |
| Album | Once More ‘Round the Sun |
When Mastodon released their album “Once More ‘Round the Sun” in 2014, the last thing I expected to find on this record was a song about regret. However, the track” Ember City” is all about that. Like many other songs on this list, this song is about the regret you feel when a relationship ends, although Mastodon manages to do this in their unique progressive metal style. What I like best about this band is that three of the members trade lead vocal duties, which allows them to have three distinct sounds in approximately five minutes.
22. Take This Bottle by Faith No More
| Genre | Alternative Metal |
| Year Released | 1995 |
| Album | King For a Day, Fool For a Lifetime |
Faith No More is widely known throughout Funk and alternative metal circles, but the track “Take This Bottle” from the 1995 album “King For a Day, Fool For a Lifetime” has more of a country flavor to it. That’s not surprising when we dive deeper into the song and uncover its meaning. In this song, Mike Patton is singing about how his drinking problem has brought his relationship to a premature end. He feels guilty for his actions and regrets the things he has done, but he can’t seem to put down the bottle.
23. Forgive Me by Evanescence
| Genre | Alternative Metal |
| Year Released | 2004 |
| Album | Sound Asleep |
Amy Lee of Evanescence has a voice that can best be described as angelic. Found on their 2004 EP “Sound Asleep,” the song “Forgive Me” describes an all-too-familiar scenario in some relationships in which one person says something that hurts the other so badly that they can’t come back from it. When Amy Lee sings the lyrics, “I’d give anything now to kill those words for you,” there is no denying that you can hear the sorrow, regret, and remorse in her voice. Unfortunately, these words can’t be taken back. It’s a little too late for that.
24. All Apologies by Nirvana
| Genre | Grunge |
| Year Released | 1993 |
| Album | In Utero’ |
Is it me, or did Kurt Cobain always sound like he was in great pain when he sang? Don’t get me wrong. I mean this in the most complimentary way. Few singers have the talent to make you feel their pain while they are singing. Cobain had the talent to do this. The 1993 album “In Utero” was filled with songs about Kurt’s pain and anger, but “All Apologies” was a semi-autobiographical recollection of his marriage to Courtney Love. Kurt blamed himself for their problems and felt guilty that they couldn’t get along.
25. When I’m Gone by Eminem
| Genre | Rap, Hip Hop |
| Year Released | 2005 |
| Album | Curtain Call: The Hits |
When Eminem released “Curtain Call: The Hits” in 2005, he included a bonus track that would go on to become one of the rapper’s most beloved songs. He has made a few songs about his daughter Haley, but this one is the most touching and heart-wrenching song of Eminem’s career. Although some of the song is fictional, the regret and guilt that Eminem feels over not being present for most of his daughter’s life are real. He wants her to know that even if he is not by her side, he is always with her.
26. Floods by Pantera
| Genre | Groove Metal |
| Year Released | 1996 |
| Album | The Great Southern Trendkill |
Groove metal pioneers Pantera are not a band you would expect to record a song about regret and guilt, but the song “Floods” from their 1996 album “The Great Southern Trendkill” has that and then some. This song is not what you would expect from Pantera, musically or lyrically. Instead, they choose to express regret for mankind’s increasingly violent nature, begging for floods to wash us all away. Philip Anselmo forgoes his angry vocal style for a somber tone, and the rest of the band follows suit, including an amazing guitar solo and outro from Dimebag Darrell.
27. at’s In the Cradle by Harry Chapin
| Genre | Soft Rock |
| Year Released | 1974 |
| Album | Verities & Balderdash |
Although this song has been covered several times by several artists, I believe the original version is still the best. Unless you’ve been hiding under a rock for almost 50 years, I’m sure you’ve heard this song at least a few times. Harry Chapin recorded the song “Cat’s In the Cradle” on his 1974 album “Verities & Balderdash,” it is about a father who regrets not spending enough time with his son while he was young. Now that the sun is grown, the father is trying to make amends.
28. Don’t Let Me Get Me by Pink
| Genre | Pop |
| Year Released | 2001 |
| Album | Missundaztood |
A lot of people think that if you want to be a famous rock or pop star, the only thing you have to have is talent. Pinks shatters that myth with the “Don’t Let Me Get Me” song from her 2001 album “Missundaztood.” This song is primarily about Pink regretting some of the things that she’s had to do to become a famous pop singer. As illustrated by the lyrics, she barely recognizes herself, “Every day I fight a war against the mirror. I can’t take the person starin’ back at me. I’m a hazard to myself.”
29. Headlights by Eminem (Featuring Nate Ruess)
| Genre | Rap, Hip Hop |
| Year Released | 2013 |
| Album | The Marshall Mathers LP 2 |
Eminem’s songs are filled with guilt, and he has had a rocky relationship with his mother, to say the least. We know this much. What makes this song from his 2013 album ” The Marshall Mathers LP 2″ so interesting and far from anything else he’s done? It’s not very often that you hear Marshall Mathers admit that he is wrong about something, but that’s exactly what he’s doing on this track. “Headlights” is about his strange relationship with his mother and how things had gotten out of hand between the two of them.
30. Give ‘Em Hell, Kid by My Chemical Romance
| Genre | Emo, Pop Punk |
| Year Released | 2004 |
| Album | Three Cheers For Sweet Revenge |
From the 2004 album “Three Cheers For Sweet Revenge,” the guys from My Chemical Romance bring us the track “Give ‘Em Hell, Kid,” which it’s about a girl who gets pregnant. This causes a great deal of regret from both the girl who got pregnant and the guy who impregnated her. He doesn’t want to stick around to see his child grow up, and she wanted to turn her life around before she got pregnant. Now, she feels like it’s too late. Neither of the people involved in this situation is particularly happy about it.
31. Baby Come Back by Player
| Genre | Soft Rock, Funk |
| Year Released | 1977 |
| Album | Player |
In 1977, the group Player had their biggest hit with the song “Baby Come Back” from their self-titled album. This track was everywhere. Without hearing it, you couldn’t turn on a rock or pop radio station. The song is about a guy who has done something wrong, although it is never specifically mentioned. We know that he feels guilty about what he’s done and regrets losing his girl. We can hear this as he sings, “Baby come back. You can blame it all on me. I was wrong, and I just can’t live without you.”
32. Hate Me by Blue October
| Genre | Alternative Rock |
| Year Released | 2005 |
| Album | Foiled |
If you have ever done something that has caused a person that you care about a great deal of pain, and you can’t find the words to apologize, put this song on from Blue October’s 2005 album “Foiled.” There are several disputes as to whom this song was written for, but Blue October’s lead singer Justin Furstenfeld said that “Hate Me” is a blanket apology to several people that he has wronged in his life. He feels lots of guilt and regrets forcing the things he has done, specifically to a former girlfriend and his parents.
33. Regret by New Order
| Genre | Dance |
| Year Released | 1993 |
| Album | Republic |
You probably know the band New Order as the group that brought you the song “Blue Monday.” However, they are more than just a one-hit-wonder; they prove it with the song “Regret” from the 1993 album “Republic.” As its title would indicate, this is a song about the regrets and pitfalls that come with being a celebrity and the lack of privacy that living that type of Lifestyle brings. This is indicated by the lyrics, “I would like a place I could call my own. Have a conversation on the telephone.”
34. Someone You Loved by Lewis Capaldi
| Genre | Indie Pop |
| Year Released | 2006 9 |
| Album | Divinely Inspired To a Hellish Extent |
“Someone You Loved” is another amazing song from Capaldi’s 2019 breakthrough album “Divinely Inspired To a Hellish Extent.” Along with many of his other tracks, this one deals with regret about love that was lost, but it’s a little different than most of his other songs. Lewis Capaldi has said that this song was written about his grandmother, with whom he had not been close for many years. Before she passed away, the two of them finally started to have a relationship. However, he regrets the time that he lost with her before they became close.
35. The Freshmen by The Verve Pipe
| Genre | Alternative |
| Year Released | 1996 |
| Album | Villains |
Coming from their 1996 album “Villains,” The Verve Pipe exploded on the music scene with the song “The Freshmen.” Because I have heard a few interpretations regarding the meaning of this song, I will present to you the one that makes the most sense to me. This song is about a young couple who got pregnant at a very young age and chose to have an abortion rather than have a baby they cannot raise. Both of the people involved feel guilty for what they have done, and in retrospect, they now regret it.
36. Fire and Rain by James Taylor
| Genre | Folk, Singer Songwriter |
| Year Released | 1970 |
| Album | Sweet Baby James |
In 1970, James Taylor released his seminal album “Sweet Baby James,” which made him an internationally known singer and songwriter. On that album was what would become his signature song, “Fire and Rain.” As the story goes, James Taylor wrote this song after one of his best friends passed away. He let us know immediately when he sings, “Just yesterday morning, they let me know you were gone. Suzanne, the plans they made put an end to you.” His biggest regret was not getting to see his friends and spending time with her again.
37. Something I Can Never Have by Nine Inch Nails
| Genre | Industrial |
| Year Released | 1989 |
| Album | Pretty Hate Machine |
Trent Reznor, the mastermind behind Nine Inch Nails, has two songs on this list. Although, I am only including one performance by him. “Something I Can Never Have,” from the 1989 debut album “Pretty Hate Machine” is a bleak track in which Trent is trying to escape the memories of a past relationship. Much to his chagrin, he is unable to accomplish this. Backed by only a piano, Reznor sings, “My favorite dreams of you still wash ashore, scraping through my head ’til I don’t want to sleep anymore.” Now, he regrets ending the relationship.
38. Mama Told Me (Not To Come) by Three Dog Night
| Genre | Classic Rock |
| Year Released | 1970 |
| Album | It Ain’t Easy |
Do you remember being younger and thinking that you know everything? Your parents would tell you not to do something, and you would just blow them off. One of your parents, specifically your mother, would tell you that you would regret not listening to them. Well, the song “Mama Told Me (Not to Come)” by Three Dog Night from their 1970 album “It Ain’t Easy” is that scenario set to music. This song is about a guy who goes to a party and ends up regretting not listening to his mother when she told him not to go.
39. Paralyzed by NF
| Genre | Rap, Hip Hop |
| Year Released | 2015 |
| Album | Mansion |
Nathan John Feuerstein, better known by his stage name NF, has been through plenty of traumatic experiences in his life. Most of them end up in his songs. The track “Paralyzed” from his 2015 major label debut album “Mansion” is about Feuerstein’s lack of emotions and the guilt he feels because he has to live this way. NF feels like he only has some self to blame, as he spits out the lyrics “I’m in a box, but I’m the one who locked me in, suffocating and I’m running out of oxygen.”
40. Sorry by Madonna
| Genre | Pop |
| Year Released | 2005 |
| Album | Confessions On a Dance Floor |
Madonna released the record “Confessions On a Dance Floor” in 2005. On that album was a song called “Sorry” that tells the tale of a woman who has been wronged by her partner, and this can’t be the first time he’s wronged her because she repeatedly says that she’s grown tired of his apologies. He is going to regret all the things he’s done to her, and doesn’t hesitate to put him on blast with the lyrics, “You’re not half the man you think you are. Save your words because you’ve gone too far.”
41. I Wish You Would by Taylor Swift
| Genre | People Country |
| Year Released | 2014 |
| Album | 1989 |
Taylor Swift has had enough relationship problems to write a hundred lists, and her 2014 track “I Wish You Would” from the album “1989” is another in a long line of heartbreaking songs from the pop country princess. In this song, Swift regrets that she lost another love and feels she could have done more to make him stay. Unfortunately, this doesn’t appear to be resolved by the end of the song, and all she’s left with are memories of what once was, again left wishing they’d never broken up.
42. Love Of My Life by Harry Styles
| Genre | Pop |
| Year Released | 2022 |
| Album | Harry’s House |
Although Harry Styles got his start in the group One Direction, he is now making waves as a solo artist, especially with tracks like. “Love Of My Life” from his 2022 album “Harry’s House.” While the song doesn’t mention exactly what happened, we know that Harry broke up with somebody for some reason. Now, he’s left to regret what he’s done, and he has to live with it. You can hear his pain as he says, “It’s not what I wanted, to leave you behind.” Sadly, that’s exactly what he’s done, and he’s paying forces it now.
43. Call Me by Shinedown
| Genre | Hard Rock |
| Year Released | 2007 |
| Album | The Sound of Madness |
Coming from the 2007 album “The Sound of Madness” is the track “Call Me” from Jacksonville, Florida’s Shinedown. Throughout this song’s run time, lead vocalist Brent Smith agonizes over ending a relationship because he knew it would be better to leave than stay. You can hear how tortured he is in the lines, “I had to make a choice that was not mine. I had to say goodbye for the last time.” He regrets ending his life with her, but he knows he needs to set her free.
44. Creep by Radiohead
| Genre | Alternative |
| Year Released | 1992 |
| Album | Pablo Honey |
When Radiohead released the album “Pablo Honey” in 1992, they had no idea that the album would go on to become an alternative rocking masterpiece with tracks like “Creep.” This song is about the narrator’s regret from not having the courage to talk to the girl of his dreams. He has his chance, but for whatever reason, he doesn’t. Instead, he chooses the self-deprecating act of focusing on what he perceives to be his negative qualities and convinces himself that he isn’t worthy of her, which is brilliantly sung by Thom Yorke.
45. Rain When I Die by Alice In Chains
| Genre | Grunge |
| Year Released | 1992 |
| Album | Dirt |
Alice In Chains’ 1992 grunge rock opus “Dirt” is one of my favorite albums of all time, thanks to songs like “Rain When I Die,” which is about a couple who choose to begrudgingly go their separate ways. The break-up was over one person being dishonest with the other. However, Layne wants to get back together, although he doesn’t know if it’s possible. He regrets what he’s done, and he feels guilty about lying as asks, “Slowly forgive my lie, lying to save me. Could she love me again, or will she hate me?”
46. Happier by Ed Sheeran
| Genre | Pop |
| Year Released | 2017 |
| Album | ÷ |
Ed Sheeran’s 2017 album “÷” is well on its way to becoming a modern classic. That’s where we find the song “Happier,” which is about a couple who has broken up, although Ed regrets that they had to part ways. Instead of being bitter about the situation, he wishes her happiness in her new relationships with lyrics like “Promise that I will not take it personally, baby, if you’re movin’ on with someone new.” Still, that doesn’t mean that he is happier without her. It just means that he realizes she is better off without him.
47. When I Look At You by Miley Cyrus
| Genre | Pop |
| Year Released | 2010 |
| Album | The Last Song |
“When I Look At You” is the latest tragic installment of Miley Cyrus’s love life. Found on the 2010 album “The Last Song,” this track tackles two subjects that are prevalent in her life. First, IT addresses the pitfalls of fame, almost to the point where she regrets ever becoming a world-famous pop star. Secondly, although her transgressions are not specifically mentioned, she has done something wrong to someone she cares deeply about. She feels guilty for what she has done and is trying to make amends. Only time will tell if she is forgiven.
48. The One That Got Away by Katy Perry
| Genre | Pop |
| Year Released | 2010 |
| Album | Teenage Dream |
Although she is typically known for writing fun pop songs about falling in love, “The One That Got Away” shows a deeper side of Katy Perry. This song from Katy’s 2010 album “Teenage Dream” is about a young couple who made plans for the future, but things didn’t work out as they had planned. Unfortunately, the two of them drifted apart and have moved on with their lives. Now, she is regretting that they ever broke up, calling him the one that got away. Sadly, he changed his number and wants nothing to do with her.
49. After Hours by The Weeknd
| Genre | Pop |
| Year Released | 2020 |
| Album | After Hours |
From his 2020 album “After Hours,” Canadian contemporary R&B artist Abel Makkonen Tesfaye, better known by his stage name The Weeknd, spins a tragic tale about the regret you feel about not having that person in your life. Now, he finds himself going through a rough period in his life, and he wishes that he still had her by his side. He makes this known with the lyrics “Oh, baby, where are you now when I need you most? I’d give it all just to hold you close. Sorry that I broke your heart.”
50. She Used To Love Me A lot by Johnny Cash
| Genre | Country |
| Year Released | 2010 |
| Album | Out Among the Stars |
In his 2010 posthumous release “Out Among the Stars,” the Man in Black gives us the song “She Used To Love Me a lot,” which is about a man who runs into his ex and regrets that the relationship ended. They sit and reminisce about old times. Sadly, as he’s getting his hopes up, she walks out the door of the Cafe. She tells him that she needs something that he can’t provide. All he can do is think about the love that they once had. He knows that he can never have it again.
51. If I Could Turn Back Time by Cher
| Genre | Pop |
| Year Released | 1989 |
| Album | Heart of Stone |
Although Cher is mostly known for songs about being in love, one of the biggest hits of her career was found on her 1989 album “Heart of Stone.” That track was called “I Could Turn Back Time,” and that’s about a relationship that was prematurely ended. Cher feels some regret and guilt that it ended and wishes she could go back in time to undo all of the damage she did in the relationship. Unfortunately, she doesn’t have access to a time machine, and there will be no second chance in the relationship.
52. How To Save a Life by The Fray
| Genre | Indie Pop |
| Year Released | 2005 |
| Album | How To Save a Life |
The Fray hasn’t gotten a lot of airplay on the radio, but they are known for the song “How To Save a Life” from the 2005 record of the same name. This song tells the familiar tale of two friends who have drifted apart. Now, one of the friends appears to be picking up committing suicide, while the other wishes that he had done more for his friend. He feels guilty that he hasn’t been there for his friend when his friend needed him the most and regrets how he let the relationship drift.
53. Title and Registration by Death Cab for Cutie
| Genre | Indie |
| Year Released | 2003 |
| Album | Transatlanticism |
Indie rock darlings Death Cab for Cutie are not the most well-known band in the world, but they have a rabid fan base that loves their 2003 record “Transatlanticism.” That album features the melancholy tune “Title and Registration,” which is about a couple who have decided to call it although they say that nobody is to blame for its demise. One of them regrets that it had to end. The poetic lyrics “And all I find are souvenirs from better times, before the gleam of your taillights fading east to find yourself a better life.”
54. Death Blooms by Mudvayne
| Genre | Alternative Metal |
| Year Released | 2000 |
| Album | L.D. 50 |
I’m not going to pull any punches. Mudvayne was one of my favorite bands of the early 2000s, and the song” Death Blooms” is one reason why. Taken from their 2000 album “L.D. 50,” this track is about someone who has grown old and feeble and is now on their deathbed. He’s not quite ready to meet his maker and regrets that he let his body regress into the feeble condition it is in. He knows that death is coming for him and is angry that he has to go before he is ready.
55. The Dream’s In The Ditch by Deer Tick
| Genre | Indie |
| Year Released | 2013 |
| Album | Negativity |
The name of the Rhode Island alternative following rock band Deer Tick’s 2013 album “Negativity” says it all, especially with songs like “The Dream’s In The Ditch.” This song is about the realization that you will not attain the aspirations that you had for yourself as a child. It’s also about the regret you feel for allowing yourself to succumb to the standards that Society has deemed necessary for a normal functioning adult. This track also warns the younger generation that if they aren’t careful, this will end up happening to them.
56. Please Forgive Me by Bryan Adams
| Genre | Pop |
| Year Released | 2003 |
| Album | So Far So Good |
Coming from the 2003 greatest hits collection titled “So Far So Good” which included his hit single “Please Forgive Me,” This crack is about a couple who have split up, but the guy still finds himself madly in love with his former partner. While he regrets that the relationship had to end, he says that his love for her continues to grow stronger, even if they’re apart. When Adams sings, “So if you’re feeling lonely, don’t. You’re the only one I’ll ever want. I only want to make it good,” it’s apparent he wants her back.
57. Sorry by Justin Bieber
| Genre | Pop |
| Year Released | 2015 |
| Album | Purpose |
Although Justin Bieber used to be known for bubblegum pop songs that were made to get you dancing but were lacking in lyrical content, his music has shown significant maturity with his 2015 album” Purpose.” One of the tracks on that album that showed the most maturity in his lyrics was the song “Sorry,” which is about a guy who regrets that he and his girlfriend broke up. However, Justin shows maturity when he says, “I’m not just trying to get you back on me because I’m missing more than just your body.”
58. Sorry For The Stupid Things by Babyface
| Genre | R&B, Soul |
| Year Released | 2005 |
| Album | Grown & Sexy |
It doesn’t take a genius to figure out what this 2005 track from Babyface’s album “Grown & Sexy” is about. It’s about a man who cheated on his girlfriend, and now he feels guilty about it. He regrets that he could trade her trust comma and is asking her for another chance to prove his worth to her. As the title would indicate, this song is an apology note to her. This track is so effective because the music and vocals are exactly what you would expect from an R&B heavyweight like Babyface.
59. Butterfly by Weezer
| Genre | Alternative Rock |
| Year Released | 1996 |
| Album | Pinkerton |
Weezer is one of the last bands that I would expect to include on a list about regret and guilt, but the song “Butterfly” from the alternative rockers’ 1996 record “Pinkerton” uses capturing a butterfly as a metaphor for keeping someone trapped in a relationship. Eventually, the relationship will die, and all you will be left with is guilt for killing the relationship and regret that it is over. I think this is one of the most underrated songs from one of alternative rock’s most appreciated and well-known bands. It’s different, but that’s what makes it great.
60. Stay With Me by Sam Smith
| Genre | R&B, Soul |
| Year Released | 2014 |
| Album | In the Lonely Hour |
Sam Smith has a soulful voice that makes him one love R&B’s up-and-coming superstars. He has a rare talent in which he can make you feel what he is feeling deep in your soul. The song “Stay With Me” is a perfect example of Sam Smith showcasing his talent, as is the rest of his 2014 album “In the Lonely Hour.” In this song, Sam paints us a picture of his lifestyle and how much he regrets not being able to find his one true love. It must be lonely at the top.
61. Guilty by Marina
| Genre | Indie Pop |
| Year Released | 2010 |
| Album | The Family Jewels |
Brilliantly backed by her band, The Diamonds, Marina is a throwback artist that reminds me of someone you would hear in a bar while sipping cocktails back in the 1940s. Taken from her 2010 album “The Family Jewels,” the song “Guilty” is about a girl who never had a relationship with her father and ran away from home at a very young age because she killed the family pet. As you could gather from the title, she feels guilty about running away from home and regrets that she never had a relationship with her father.
62. You Could Be Happy by Snow Patrol
| Genre | Alternative, Indie, Pop |
| Year Released | 2006 |
| Album | Eyes Open |
The Indie alternative group Snow Patrol released their album “Eyes Open” in 2006. On that album was a bittersweet track called “You Could Be Happy.” In this song, the guy feels like he is holding the girl back from achieving her dreams, so he lets her go as he says, “Do the things that you always wanted to do without me there to hold you back. Don’t think, just do.” What he’s saying is that he doesn’t want her to dwell on things. He just wants her to live her life to the fullest.
63. So Sorry by Feist
| Genre | Pop |
| Year Released | 2006 |
| Album | The Reminder |
From her 2007 album” The Reminder,” Leslie Feist, also known simply as Feist, released the simplistic track called “So Sorry,” which is an apology that she issues to her former lover for many things, including being selfish. In the track, the Canadian-born indie folk singer acknowledges that the breakup was her fault and regrets that it had to happen. In the song, she says that the couple does not need to apologize, but she always feels sorry after the other person is gone. Unfortunately, it’s too little too late. In terms of songs about guilt, this one is pretty legendary.
64. Jealous Guy by John Lennon
| Genre | Classic Rock |
| Year Released | 1971 |
| Album | Imagine |
Although John Lennon is mostly known for the time he spent as the lead singer for The Beatles, he also had a huge solo career. “Jealous Guy” is widely known throughout his fan base, and is a song about how jealousy can corrupt an otherwise perfect relationship. Throughout the song’s first half, he is apologizing for how his jealousy will win the relationship and makes an emotional mess out of his ex. However, in the song’s last lines, he continues to say that he’s a jealous guy.
65. Suedehead by Morrissey
| Genre | Alternative Rock |
| Year Released | 1988 |
| Album | Viva Hate |
In 1988, Steven Patrick Morrissey ( better known by his stage name Morrissey) released his alternative pop record “Viva Hate,” which featured a song that would go on to become a classic in his repertoire. That song was called “Suedehead” and is a complicated story about a recently broken-up couple. Morrissey, who ended the relationship, is being stalked by the person he no longer wants to be with. Needless to say, this makes his life a living hell, and he regrets ever being with that person in the first place.
Wrap Up:
We hope you enjoyed our list of songs and you found some new ones to add to your playlist. Let us know if you know of any songs that we missed in the comments section below!
Hi, my name is Kevin and I’m from Butler, Pennsylvania. I’ve been obsessed with music and audio gear for as long as I can remember. I started this website to help people find professional advice related to a wide range of audio topics. We have a number of Audio Engineers on our team who have been designing and fixing audio gear for decades.