19 Best Songs about Regret and Making Mistakes

regret label on filing cabinet

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!

‘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.”

‘Jealous Guy’ appeared on Lennon’s first post Beatles album, ‘Imagine’, which was produced by the controversial Phil Spector. It was also covered by Brian Ferry some years later.
 

‘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.

Their 1983 breakthrough hit ‘Blue Monday’ become the best-selling 12″ release of all time, selling over 3 million copies worldwide.
 

‘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.”

Mike Rutherford was the bass player (and later the guitarist) for Genesis. Mike + the Mechanics started out as a side project.
 

‘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.”

Phil Collins is one of only three musicians (Paul McCartney and Michael Jackson are the other two…good company there) to have sold over 100 million albums globally.
 

‘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).

Lewis is a second cousin of the Doctor Who actor Peter Capaldi.
 

“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!

James Taylor was one of the first singer/songwriters of the ’70s. Until this point, most hits were often written by one person and performed by another, or written and performed by a group or partnership (e.g. Jagger/Richards, Lennon/McCartney).
 

‘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.”

The name ‘Death Cab for Cutie’ comes from a song of the same name by the avant garde ’60s band ‘Bonzo Dog Doo-Dah Band’.
 

‘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.”

Despite a career that spanned six decades, James is still relatively unknown. Her influence is incalculable though. Everyone from The Rolling Stones to Paloma Faith has credited her as a huge inspiration.
 

‘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.”

The track was given to Prince’s side project (called ‘The Family’) before Sinead O’Connor made it a hit in 1990. He also played it at his last ever show, in Atlanta on 14 April 2016.
 

‘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.

Cash summoned some great musicians to accompany him on the the track, enlisting Mike Campbell and Benmont Tench of Tom Petty and the Heartbreakers (well, how could they say no!…It was Johnny Cash for crying out loud!).
 

‘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.

Chapin was an American singer-songwriter, philanthropist, and a dedicated humanitarian who fought to end world hunger. He tragically died in a traffic accident at the tender age of 44, while en route to perform at a free benefit concert in New York. Sometimes the best die young.
 

‘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.”

Steven Demetre Georgiou – aka Cat Stevens – became a Muslim and changed name to Yusuf Islam in 1977.
 

‘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”).

‘Butterfly’ alludes to the opera Madama Butterfly by Puccini.
 

‘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.””

Swift fans generally believe the song is about American actor Taylor Lautner, but she has never divulged who the unlucky recipient was.
 

‘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.’

Singer Arthur Lee was jailed for 12 years in 1995 for shooting a neighbor who asked him to turn his stereo down.
 

‘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.

Always one for random literary references, Morrissey got the name ‘Suedehead’ from a book by British author Richard Allen about British ‘skinheads’: a counterculture group that started in the late ’60s who were given a boost in in the ’70s with the arrival of punk.
 

‘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.”

As well as a successful career as a solo artist, Feist is also part of a Canadian music collective called ‘Broken Social Scene’ known for its grand orchestrations featuring an array of instruments and unusual song structures.
 

‘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.

‘Baby Come Back’ falls into the rather bizarre music category of “Yacht Rock”! Soft, mellow and slightly maligned.
 

‘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.”

The music video was filmed on board the USS Missouri with the crew. Cher told Q magazine in 2013: “They were real sailors too. They were funny. They kept calling me ‘ma’am.”
 

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

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