It’s better to live without regret. But for most of us mere mortals, that’s nigh on impossible.
A friendship we’ve let slip, a tricky relationship with a parent or sibling we wish was better, something we said in the spur of the moment to a colleague. We all make mistakes sometimes and have to live with the consequences.
Musicians are no different. Being on the road and away from your family can be a huge source of tension and guilt. So it’s no surprise that songs about regret are common as muck!
So here’s our pick of the best regret songs. If you want a life without it, take heed!
Table of Contents
- ‘Jealous Guy’ by John Lennon
- ‘Regret’ by New Order
- ‘The Living Years’ by Mike + The Mechanics
- ‘Against All Odds (Take A Look At Me Now)’ by Phil Collins
- ‘Someone You Loved’ by Lewis Capaldi
- “Fire and Rain” by James Taylor
- ‘Title and Registration’ by Death Cab for Cutie
- ‘Damn Your Eyes’ by Etta James
- ‘Nothing Compares 2 U’ by Sinead O’Connor
- ‘Hurt’ by Johnny Cash
- ‘Cat’s in the Cradle’ by Harry Chapin
- ‘Father and Son’ by Cat Stevens
- ‘Butterfly’ by Weezer
- ‘Back to December’ by Taylor Swift
- ‘Alone Again Or’ by Love
- ‘Suedehead’ by Morrissey
- ‘So Sorry’ by Feist
- ‘Baby Come Back’ by Player
- ‘If I Could Turn Back Time’ by Cher
- More Songs About Regret
‘Jealous Guy’ by John Lennon
It’s well documented what a complex character John Lennon was. A troubled upbringing made sure of that.
Never one to shy away from sharing his emotions or his insecurities (listen to the Beatles song ‘Help!’ or ‘I’m a Loser’), here we see John in reflective mode.
He regrets his behavior, “I didn’t mean to hurt you, I didn’t mean to make you cry,” but concludes it’s because he’s a “jealous guy.”
‘Regret’ by New Order
From the British alternative rock band New Order, ‘Regret’ is a beautifully cryptic song about regret and was, according to their bass player Peter Hook, the “last good New Order song.”
The words are open to interpretation (of course), but here regret is personified: “You were a complete stranger (you=regret), now you (regret) are mine.”
He laments how he treated others (“I was a short fuse / Burning all the time”) and wishes he could wake up not feeling riddled with guilt about it (“a place to call my own”) and “have a conversation on the telephone” about it.
But he’s doesn’t. And he knows if he waits for tomorrow, they’ll fall apart (a reference to death?).
Easily one of the best songs about regret on the list.
‘The Living Years’ by Mike + The Mechanics
Troubled family relationships are often a source of material for songwriters. ‘The Living Years’ is right up with one of the most heartfelt of the lot. It’s written from the point of view of a son – in this case, frontman Mike Rutherford – who had a problematic relationship with his father.
After his dad’s death, he regrets not communicating more with him while he was alive “in the living years.”
But life goes on, and he finds solace when his own son is born: “I’m sure I heard his echo / In my baby’s newborn tears.”
‘Against All Odds (Take A Look At Me Now)’ by Phil Collins
It’s well documented that The breakup of his marriage primarily fueled collin’s bestselling album Face Value. The album features its fair share of betrayal songs such as ‘In the Air Tonight’.
In this power ballad, he implores his wife to “take a look at me now” – he knows a reconciliation is unlikely “against all odds,” but it’s a chance he has to take.
His wife had taken off with the kids and left him home alone. In a 2007 interview for the radio show This American Life, He said, “if that personal stuff had not happened to me at the time, I probably would never have made an album.”
‘Someone You Loved’ by Lewis Capaldi
Have you ever let your guard down in a relationship, then got trodden all over?
That’s the premise of this modern classic by Scottish singer/songwriter Lewis Capaldi with that distinctive baritone voice. The narrator deals with the end of a relationship with a romantic partner: “I let my guard down / And then you pulled the rug / I was getting kinda used to being someone you loved.”
It’s also a song about trust. He thought they had something going, then she walked out in his time of need (according to interviews, he was dealing with a family bereavement at the time – the sudden loss of his grandma).
“Fire and Rain” by James Taylor
The lyrics talk about his reaction to the suicide of his childhood friend (Suzanne Schnerr) and his experiences with drug addiction and depression.
Taylor has just been signed by Apple Records (the Beatle’s label) and was recording his first album in London. But, much to his dismay, the news of his friend’s death was held back from him for six months so he could focus.
Carole King, who played piano on the song, took inspiration from the song when she wrote her famous song about friendship, “You’ve Got a Friend.” According to King, it was a response to the line, “I’ve seen lonely times when I could not find a friend.” How sweet!
‘Title and Registration’ by Death Cab for Cutie
Imagine finding an old photograph in the glove compartment of your car.
The photo is of an ex-lover you’d long since forgotten. You were rummaging for a travel sweet (well, in the song, he’s “searching for some legal document,” hence the title of the song), and now you’re suddenly reliving the past.
“When you’re not expecting to run into stuff like that, it affects you the most,” said writer Ben Gibbard in a Rolling Stone interview.
“There’s no blame for how our love did slowly fade / And now that it’s gone, it’s like it wasn’t there at all / And here I rest where disappointment and regret collide / Lying awake at night.”
‘Damn Your Eyes’ by Etta James
We’re our own worst enemies. That’s the gist of this number from brilliant R&B singer Etta James.
It’s a song about a crush on a guy. Etta James here is like a moth to a flame – she can’t help herself, even though she knows it’s terrible for her.
“You keep deliberately deceivin’ me / Makin’ me see what I want to see / Damn your eyes.”
She regrets getting involved. For “getting my hopes up high / For making me fall in love again.”
‘Nothing Compares 2 U’ by Sinead O’Connor
The Purple One – aka Prince – wrote ‘Nothing Compares 2 U’. It was Sinead O’Connor, however, who made the definitive version. So much so that his version sounds like a cover!
The protagonist can’t get rid of this feeling. She “can eat my dinner in a fancy restaurant,” but nothing she does will “ever take away these blues.”
There’s plenty of regret here, too: “I know that living with you baby was sometimes hard / But I’m willing to give it another try.”
‘Hurt’ by Johnny Cash
‘Hurt’ is a song by American industrial rock band Nine Inch Nails, but better known for the Johnny Cash cover of the song that received commercial and critical acclaim. A BBC poll voted it the second greatest cover version of all time (below Pet Shop Boy’ ‘Always on My Mind’).
The music video, in particular, met received huge plaudits. Music publication the NME heralded it as the greatest music video of all time.
‘Cat’s in the Cradle’ by Harry Chapin
Here’s a tale about not putting your career before your family.
‘Cat’s In The Cradle’ tells the story of a dad who doesn’t put the time in with his young son to share those little moments – he’s always too busy working. When the child has grown up, it’s too late. In a twist of fate, the son now has no time to spend with his father.
This great song about missed opportunities reminds parents not to fritter away those precious years working at the expense of time with your kids.
Listen to it, then clock off early today and play with your little ones.
‘Father and Son’ by Cat Stevens
Growing up is all about working things out for yourself. You need to make your own mistakes – and often that entails going away – the worst thing a parent can do is stand in their way.
In this poignant song by Cat Stevens, a father is counseling his son. He implores him to “settle down, find a girl, if you want you can marry” because that’s what he did, and it turned out well for him “look at me, I am old, but I’m happy.”
But the son isn’t convinced. “From the moment I could talk, I was ordered to listen / Now there’s a way, and I know that I have to go away.”
‘Butterfly’ by Weezer
Weezer fans generally consider the stripped-back acoustic number ‘Butterfly’ as one of the band’s best.
Frontman Rivers Cuomo sings about catching a butterfly “with my momma’s mason jar” only to find the insect has withered away when he wakes the next day.
The lyrics are open to interpretation. Some interpret it as being about forced sex (“I did what my body told me to”).
‘Back to December’ by Taylor Swift
How about the guilt you feel when you’ve done someone wrong? If you’ve ever done the dirty on someone, you’ll know all about that feeling.
In this song, we see Taylor apologizing for the way she treated an former boyfriend. She said in an interview for E! News “This is about a person who was incredible to me, just perfect to me in a relationship, and I was really careless with him.””
‘Alone Again Or’ by Love
The peculiar titled ‘Alone Again Or’ appeared on their seminal LP Forever Changes from celebrated West Coast psychedelic rock band Love. For many people, the song embodies ‘the summer of love’ of 1967.
There’s a sadness to the song. In many ways, it’s about unrequited love. A realization that his lover won’t appear because “you’ll do (just what) you choose to do” and an admission that he’ll be “alone again tonight.”
Filmmaker Wes Anderson’s used the song to great effect in his first movie, ‘Bottle Rocket.’
‘Suedehead’ by Morrissey
His first single after the demise of the Smiths in 1988, ‘Suedehead’ appeared on his debut solo album Viva Hate and marked a new beginning for the acerbic Morrissey.
The song is full of remorse, and despite Morrissey’s claim that the song’s subject was apparently about Morrissey’s teenage years, it’s hard to believe it’s not about the split of The Smiths (in part, at least).
It’s a breakup song about lost love. In the end, he writes off the relationship with the callous remark, “it was a good lay.” Coming from Morrissey, who advocated celibacy as a way of life, it was pretty shocking! When quizzed about the lyric, Morrissey said, “Well, it was actually ‘a good lay’. I just thought it might amuse someone living in Hartlepool.”
The video was shot in the streets of Fairmount, Indiana, where James Dean (one of his inspirations) grew up.
‘So Sorry’ by Feist
Here we see singer Leslie Feist lamenting her actions. She has driven away someone again, and she’s “so sorry” for doing it.
However, there’s an admission that they’re both to blame. The narrator regrets: “We’re so helpless / We’re slaves to our impulses / We’re afraid of our emotions.”
The song ends on an optimistic note: “We don’t need to say goodbye / We don’t need to fight and cry / We, we could hold each other tight tonight.”
‘Baby Come Back’ by Player
Their biggest tune by a country mile for the band Player, ‘Baby Come Back’ was a huge hit, reaching #1 on the US Billboard Hot 100. It even earned them a record deal!
The song has cropped up in random places, including The Simpsons (in the episode Homer Alone when Homer manages to lose Maggie – the song is the hold music when he calls the “Department of Missing Babies”). It’s also in the blockbuster movie Transformers.
I’m sure writers Peter Beckett and J.C. Crowley didn’t mind one bit.
‘If I Could Turn Back Time’ by Cher
The adage ‘The pen is mightier than the sword’ is relevant here. Words have untold power.
Here we see Cher asking for forgiveness for the things she’s said to her lover: “Words are like weapons, they wound sometimes.”
She misses him and wants him back, but it’s too late: “If I could turn back time / If I could find a way / I’d take back those words that’ll hurt you / And you’d stay.”
More Songs About Regret
- ‘Always On My Mind’ by Willie Nelson
- ‘Bad Day’ by Justin Bieber
- ‘Amoreena’ by Elton John
- ‘7 Minutes’ by Dean Lewis
- ‘Tryin’ To Love Me’ by Jason Aldean
- ‘Number 37405’ by Tim McGraw