In artistic terms, there can be little doubt that regret has remained one of the most popular themes addressed by pop songwriters. Sometimes falling in love means falling out of love. Sometimes risking it all means losing it all. Many of the following ten songs evoke the strong feelings of regret that often accompany breakups or the break-down of family relationships.
As these songs show, moreover, songs about regret can be one of the most powerful emotions that a musician can use to connect with an audience.
Best Songs About Regret
“Against All Odds” – Phil Collins
As everyone knows, it can be extremely difficult to move on from a relationship that hasn’t worked out, and Phil Collins knew intuitively that regret often constitutes the biggest part of a falling out with someone.
“Against All Odds” remains one of Collins’s most touching odes to lost love; for anyone who relishes a well-written ballad, it’s hard not to get weepy-eyed at this true heartbreaker of a song. Musically, “Against All Odds” remains one of the finest evocations of regret ever released.
“Is It A Crime” – Sade
As is often true in life, sometimes a breakup causes us to discover that our minds and our hearts are moving in different directions from one another. We know that we should move on with our lives, for example, but the emotional pull towards the object of our affections is still as strong as ever.
On “Is It A Crime,” Sade expresses this truth in the aptest and poetic way possible: Even by her own high songwriting standards, the song is profoundly moving.
“Father and Son” – Cat Stevens
Almost certainly one of the best songs about generational divides ever written, “Father and Son” by Cat Stevens describes the way in which our failure to connect with our families or live up to the expectations of others can often lead to deep regrets at a later time. While “Father and Son” certainly doesn’t feature Stevens at his most upbeat, the song does show us that we aren’t alone in our struggle to be heard and to make our own way in the world.
“Hey Jealousy” – Gin Blossoms
While the Gin Blossoms‘ song Hey Jealousy has a catchy chorus and was a chart-topper in the 90s, the lyrics actually talk about deep regrets. They tackle both ongoing alcohol abuse and failed relationship. With lyrics like:
Cause all I really wants to be with you
Feeling like I matter too
If I hadn’t blown the whole thing years ago
I might be here with you
It’s a sobering song about a lifetime of regrets and lost connections.
“Goodbye Yellow Brick Road” – Elton John
For most people, there comes a time in life when it becomes essential to lay aside the naiveté of youth. This process can elicit many feelings of regret, it is true, but casting away cherished illusions was never going to be an easy proposition for anyone.
Over the course of a scant three minutes, however, Elton John shows us that regret can be a powerful tool in eliciting personal change for the better. Not just a remarkable expression of regret, “Goodbye Yellow Brick Road” may just be John’s magnum opus as a songwriter.
“Knowing Me, Knowing You” – ABBA
One of ABBA’s biggest hits, “Knowing Me, Knowing You” describes the kind of regret that can emerge from the ashes of a dysfunctional relationship.
The band was in top form when the song was first released in 1976, and fans have since made it one of their most cherished ABBA tunes. Don’t let the upbeat pop production on the track fool you: This may just be one of the saddest songs ever written about the end of a relationship.
“Regret” – New Order
Formed from the ashes of Manchester rock band Joy Division, New Order adopted a deeply minimal sound throughout the 1980s that evoked the industrial landscape of their hometown.
With “Regret,” however, the band decided to flesh out their electronic sound with a decidedly bright and dense approach to pop production. Despite its sad subject matter, “Regret” became the band’s biggest hit after the song was released in 1993. The song remains a fan favorite at the band’s increasingly rare live shows.
“Out of Touch” – Hall & Oates
Bombastic 1980s synth pop doesn’t get much more intense than Hall & Oates’s 1984 hit “Out of Touch,” but the 80s production sheen on this standout pop tune masks the deep sense of longing that is expressed in the song’s lyrics.
Strangely enough, songwriter Daryl Hall didn’t think that “Out of Touch” would fit with his group’s sound. But after being convinced by a friend that the song could be a hit, the songwriter turned the track into one of Hall & Oates’s signature crowd-pleasers. Regret has never sounded quite as sweet as it does here.
“Ballad of Big Nothing”- Elliot Smith
It would be redundant to say that Elliott Smith often turned to melancholy subject matter over the course of his short musical career. But “Ballad of Big Nothing” is sad even by Smith’s woebegone standards.
Examining a string of broken relationships and disappointments with almost surgical precision, Smith uses the feeling of regret here as a vehicle to get to the core of human experience.
This is not easy listening by any means, but Smith’s incredible capacity for expressing a deep atmosphere of sadness via Paul McCartney-esque chord progressions and melodic whimsy really has to be heard to be believed.
“Alone Again Or” – Love
Another great song about the fallout from a breakup, “Alone Again Or” sees Love songwriter Arthur Lee attempt to remain optimistic even while he is struggling with feelings of isolation and regret.
Largely ignored by the general public when it was first released in 1967, the track has since garnered a reputation as a 1960s pop songwriting landmark among music aficionados. Moreover, “Alone Again Or” is undoubtedly the crown jewel in Arthur Lee’s legendary songwriting career.
“That’s Really Super, Supergirl” – XTC
XTC was one of the most promising acts to emerge from the British New Wave scene of the 1980s, but principle songwriter Andy Partridge was never quite at home with the notion of being a popular rock star.
A bad case of chronic stage fright sent the composer into a tailspin at the height of XTC’s career, but Partridge elected to use his time away from the stage to recreate the sounds of his favorite 1960s pop acts in the studio.
The results were a resounding success: In its melodic delineations on the theme of regret, “Supergirl” brought the psychedelic sensibilities of 1960s songwriters like Brian Wilson and John Lennon rushing into the clean-cut atmosphere of the 1980s pop world.
That Partridge was able to equal his musical idols remains one of music’s great feats.
“Slow Dancing In A Burning Room”- John Mayer
There are certain emotions that overwhelm us when we have a crush on someone. Not too many songs tug on the heart strings in a similar fashion. On John Mayer’s “Continuum” album, “Slow Dancing In A Burning Room” is probably the most romanticized, eliciting feelings of raw love and overpowering desire. This song is about what it’s like to have a crush on someone and also explores what can go wrong. Slow dancing in a burning room is a metaphor for what it’s like when you love someone when it doesn’t always work out.
“I Could Have Lied” – Red Hot Chilli Peppers
The Red Hot Chili Peppers album “Blood Sugar Sex Magik” featured many hits, yet “I Could Have Lied” might be one of the only few truly about crushes. This song takes a somber melody and approaches listeners with a rather sad tone. It’s not easy when you have a crush--there may be things about yourself you don’t want them to know. That’s exactly what this song is about: telling the truth to your crush when you don’t want to.
“Just The Way You Are” – Bruno Mars
Our crushes always seem perfect. Bruno Mars exemplifies this point in “Just The Way You Are.” We’re attracted to our crush because it’s like they don’t even have to try. In this song, Bruno Mars sings about all the things our crushes do to perfection with such little effort. It’s a hit.
“Baby” – Justin Bieber
The song “Baby” by Justin Bieber takes a light-hearted approach to having a crush. This song is jam packed with happy melodies that are great for dancing. In this song, Justin Bieber talks about what it’s like to have a crush when you’re a teenager. Almost anyone can relate to it, there’s nothing quite like young love. This song can be heard on the radio, in clubs, and blasting through people’s headphones.
“Nothin’ On You” – B.o.B
When we have crushes, it can be difficult assessing the situation with others that might have a crush on you. In “Nothin’ On You,” B.o.B describes what it’s like when the whole world wants you, but you only want someone else. We can all relate to that feeling of being crushed on, however the heart wants what it wants. That’s why B.o.B says “they”--aka other girls--“got nothin’ on you,” because he sees the beauty in only one other girl.
“Love Story” – Taylor Swift
We like to fantasize about our crushes being “the one.” It doesn’t always work out, however the feeling is strong. “Love Story” is all about fantasizing about your dream wedding with your dream crush. Taylor Swift is no beginner when it comes to songs about crushes. This is arguably one of her most popular songs. She combines a smooth melody with memorable lyrics of love.
“Stacy’s Mom” – Fountains Of Wayne
OK--let’s get real. We all know what it’s like when we find someone a bit older than us attractive. “Stacy’s Mom” is all about having a crush on one of your friend’s moms. To make it even more awkward, it’s also about when someone of the opposite sex has a crush on you, but you can’t take your eyes off their mom. It’s a silly, light hearted hit for the ages.
“Sweet Child O’ Mine” – Guns N’ Roses
The Guns N’ Roses know how to combine a memorable guitar rift with meaningful lyrics. Even though the band thought this song wouldn’t be popular, “Sweet Child O’ Mine” became one of the most iconic crush songs of all time. Believe it or not, this song was originally written as a poem for the lead singer’s girlfriend. The song is still relevant in today’s music marketplace.
“All You Need Is Love” – The Beatles
Our crushes can seem like the savior to all our problems. In the darkness of life, our crush emerges as a bright light that ignites the soul. The Beatles make this relevant in “All You Need Is Love.” This song is all about how your crush can seemingly fix any problem. No matter how down you may seem, your crush is right there to lift you up.
“Long Hot Summer Night” – Jimi Hendrix
Jimi Hendrix has always worn his heart on his sleeve. This slick blues master knows how to blend his blues licks with songs that speak to the soul. “Long Hot Summer Night” is about wondering where your crush is, hoping they come find and rescue you. Hendrix uses a plethora of imagery, drawing on visions of nature and everyday objects to paint a picture of a lovestruck lover stuck in the heat of summer.
“Don’t Think I Don’t Think About It” – Darius Rucker
In this song, the singer vows never to return to his lover, who has since vanished from his life, married, and went on with her life. He regrets what he’s done and wants to reclaim her affection.
His feelings are expressed as the lips of an angel/still taste like sin – meaning that even if she is no longer with him, he still misses their moments together. She’s the girl he has always been curious about, and now she’s married to someone else. This makes it one of the best expressions of regret ever recorded.
“The Greatest Man I Never Knew” – Reba McEntire
It is a remorseful song about never genuinely connecting with a loved one while staying in the same house. A young girl grows up with a gloomy father who never expresses his love to her as he’s always preoccupied with other commitments.
This forces the daughter to isolate herself in her room but has no idea that she is the most important person in his life. Now that he’s been deceased for a year, the chance to form a genuine, long-lasting relationship has passed her by. Indeed a fine masterpiece to express regret.
“Stay With Me” – Sam Smith
Just by listening to it, it’s easy to realize that the song is about regrets from one lover to another. The passionate vocal delivery of Sam Smith makes it simple to feel the suffering he is experiencing. There is a touch of regret in a few lyrics of the song, but the persona wants the other person to stay with him while knowing the relationship won’t work. It is lyrically strong, making it one of the best songs for expressing regrets.
“The Living Years” – Mike and The Mechanics
This song conveys a story about generational guilt and regrets about familial connections, which can be equally as unpleasant as, if not more severe than, regrets about love relationships. It’s told through the eyes of a boy who had a tumultuous relationship with his father.
Now that the father is dead, he regrets not communicating more with him. This isn’t easy listening by any means, but it has a remarkable ability to convey a deep sense of loss and regret.
“Hello” – Adele
Adele’s latest single is about wasted opportunities for reconciliation. The Grammy-award-winning, chart-topping singer has made one thing very clear in her music over and over again: She regrets breaking it off with someone special. Hello is a song about reconnecting with an old flame and realizing that it’s all too late to rectify a relationship gone wrong.
Many of us find it difficult to swallow our pride and confess that we are at fault, and it gets even more complicated when our attempts to reach out to the person are ignored or brushed off thoroughly. The song is incredibly emotional, even by her high songwriting standards.
“A Song for You” – Amy Winehouse
The song veiled apology for all that went wrong in a relationship. In this song, Amy Winehouse admits to misbehaving toward someone close to her, and she appears to regret it. While still in a relationship with someone, we may recognize that we’ve not behaved in the manner they would expect us to. This, without a doubt, is the pinnacle of Amy Winehouse’s illustrious songwriting career.
“Tears in Heaven”- Eric Clapton
The song earned Eric Clapton nine Grammy nominations, where he took home six awards in total. However, the tale behind the music, not the honors, distinguishes this song. There is no regret more devastating than losing someone you adore. Clapton’s son, sadly, fell out of an apartment window, and it’s a result of this that he wrote the song.
“Best I Ever Had”- Vertical Horizon
Sometimes it’s easy to disregard certain aspects of a relationship as not being important enough. In most cases, however, we soon realize that these unimportant parts added up to make us so happy in a relationship.
The song is about regretting the loss of someone you love and care about. The track’s lyrics, paired with the gloomy soft rock background, make it a genuinely devastating listen. This may be one of the saddest songs about the end of love ever penned.
“When I Was Your Man” – Bruno Mars
When the person you loved the most is now happy with someone else, it’s a new kind of heartache and regret. Unlike any other song, he used every word to depict anguish as he recounts how he was so wrapped up in his misery that he lost sight of his former partner’s feelings. It’s never easy to let one’s feelings out, but this is the best.
“Photograph”- Nickelback
We all have fond childhood memories with friends and family we grew up with. The song is for all of our childhood memories that we’ll never be able to forget. It’s about saying goodbye to the people and places you grew up with and in, with a tinge of sadness that you weren’t able to keep these connections alive, now that we are all grown and taking different paths.
Born and raised in Austin, David is a dedicated writer and avid fragrance lover. When he's not trying out perfumes, he enjoys traveling and exploring new restaurants.