20 Best Songs About Regret

Richard Ellison

We’ve all had moments where we wish we could take back something that we did or said, but it’s almost impossible to go back in time and correct the mistakes of our pasts. If only there were a way to bring up these regrets from your past to apologize for them – then you’d have every reason to feel ashamed. Fortunately for us, there are songs that express this regretful sentiment, and if you’re a human being, chances are you’ve listened to at least one of the following songs without realizing it.

By the way, if you’re a fan of songs about regret, you might also enjoy songs about being sorry, songs about mistakes, and songs about old love.

Time After Time – Cyndi Lauper

Cyndi Lauper - Time After Time (Official HD Video)

Lest we forget about Cyndi Lauper , here is a classic ballad about wishing you hadn’t let your time with your special someone slip through your fingers. The lyrics tell us that time after time, you can go back and experience the good times one more time.

Dear John – Taylor Swift

Even teeny-bopper country starlet Taylor Swift has written a song about regretting an old flame. The story is told through the perspective of the dumpee, looking back on how it ended with bitterness in their heart.

Bittersweet Symphony – The Verve

The Verve - Bitter Sweet Symphony

This song muses on the irony of a bittersweet symphony being played within someone’s heart. According to the lyrics, life is full of these types of bittersweet moments.

Every Rose Has Its Thorn – Poison

Poison-Every Rose Has Its Thorn

The name says it all, doesn’t it? This ballad is about loving somebody so much that you feel like your heart will explode with regret when they leave you behind for someone else. The speaker in the song would give anything to get their lover back, even if it means becoming a thorn in their side.

One of Us – Joan Osborne

Joan Osborne - One Of Us

Regretting the things you wish for is also an important theme. In this song, we find out that our speaker would rather be a nobody than a somebody with a famous lover who obviously doesn’t appreciate them.

Ever Fallen in Love (With Someone You Shouldn’t’ve) – Buzzcocks

The Buzzcocks - Ever Fallen In Love (With Someone You Shouldn't've)

I guess we all make bad decisions every once in a while. This one of the best songs ever written about creeping up in your lover’s bedroom and realizing that they’re not someone you should be with at all. The way it’s told makes this sound like such an epic mistake (which it is, by the way).

Heart Shaped Box – Nirvana

Nirvana - Heart-Shaped Box (Official Music Video)

This is another one about you’re-not-good-for-me lovers, but this time it’s told from the perspective of someone who thinks their lover is bad for them. It leads us to believe that maybe the speaker will never be able to shake their self-destructive habits.

The Downeaster Alexa – Billy Joel

Billy Joel - The Downeaster 'Alexa' (Official HD Video)

We love this folk song about struggling with the decision of whether or not to abandon your pursuit of a life at sea for something more stable on land. I can’t help but feel conflicted while listening to it, because we admire the speaker’s passion, but their current lifestyle really doesn’t seem that fulfilling.

Somebody That I Used to Know – Gotye

Gotye - Somebody That I Used To Know (feat. Kimbra) [Official Music Video]

Maybe you regret falling for somebody just because they think they’re cooler than you, but then you realize that who you could’ve been with is worse in the long run. Here we have a classic tale of young love lost when an ex-girlfriend leaves for somebody else.

I’m Not Okay (I Promise) – My Chemical Romance

My Chemical Romance - I'm Not Okay (I Promise) [Dialogue/MTV Version]

Similar to “Bittersweet Symphony,” this song is about realizing that your life now is worse than the one that you had before. This time, though, it’s told from the perspective of someone who has missed their chance to alter the course of their life after making a mistake.

Landslide – Fleetwood Mac

Fleetwood Mac - Landslide (Official Music Video) [HD]

This is one of the best songs ever written about regretting a breakup, and it’s so simple. The speaker regrets letting their lover go – that’s all there is to it – but they have to accept it for what it is.

Someone Like You – Adele

Adele - Someone Like You (Official Music Video)

Here we have a song about realizing that the way you treated somebody was wrong after they left. We all wish to go back in time and tell our past selves not to do what you know you shouldn’t have done, but it’s just an impossibility.

Gypsy Road – Cinderella

Cinderella - Gypsy Road

A lot of songs on this list are about realizing that the person you lost is actually someone you didn’t want, but this one takes it back a step. The speaker in this song regrets letting their lover go even before they’ve left, knowing full well that they’ll probably never feel the same way again.

Waterloo Sunset – The Kinks

The Kinks - Waterloo Sunset (Official Audio)

Picking up where “Gypsy Road” left off, this song is about regretting letting a relationship drag on even as it’s dying. We all have those people we wish we could go back and tell not to waste their time waiting for us, but if only it were that simple.

Ain’t No Sunshine – Bill Withers

Bill Withers - Ain't No Sunshine (Official Audio)

In all of the best songs about regret, one thing always rings true: the regret is never totally gone, no matter how much time passes. This one sounds like an old man’s song, but it could be acted out by a young person as well.

Slide – The Goo Goo Dolls

Goo Goo Dolls - Slide [Official Music Video]

This is another great song about wanting somebody to come back even though you know they wouldn’t want to be with you in the first place. There’s a certain point where we realize that we’re chasing somebody who doesn’t deserve to be chased, and it’s hard to accept.

Tangled Up in Blue – Bob Dylan

Bob Dylan - Tangled up in Blue (Official Audio)

Some regret is more manageable than others; this is one of the best songs about such feelings. It seems like it’s a song about someone who misses their old lover, but it’s actually more complicated than that.

Stay – Sugarland

Sugarland - Stay (Official Video)

Here we have one of the best songs about regretting a breakup, but it’s more complicated than that. It’s also about wishing you didn’t have to let your lover go just so they could be happy without you.

Mr. Brightside – The Killers

The Killers - Mr. Brightside (Official Music Video)

This is another song about having mixed feelings about a relationship, except it’s told with more contempt than the others on this list. The speaker knows that they shouldn’t be thinking what they’re thinking, but it’s difficult to control your thoughts when you’re in love (or lust).

Love the Way You Lie – Eminem ft. Rihanna

Eminem - Love The Way You Lie ft. Rihanna

This is more complicated than some of the simple relationship regrets on this list, but it’s one of the best songs about regret. The speaker is involved in a dangerous, abusive relationship but they can’t stop themselves from going back for more punishment.