10 of the Most Crushing Songs About Regret

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10 of the Most Crushing Songs About Regret

Regret’s a funny thing. That malleable sentiment takes form in any number of ways. It’s a state of mind, something you let go of, or live through. It’s a decision you made, but maybe shouldn’t have. And while we all try to live our lives with as few as possible, here are 10 of the most intense songs to help you deal with different regrets.

1. Etta James, “Damn Your Eyes”

For: The one you can’t let go of

This is a song about regretting the person you can’t escape. Etta James sings, “I gave myself a good talking to, no more being a fool for you.” Throughout the song she returns to the line “damn your eyes for taking my breath away, for making me want to stay.”

It’s a defiant song made possible with the broad emotional tones that James’ unique voice brings to the song. The brass section reinforces the message. A trombone solo dances along the melody before James comes in to repeat the refrain. But it’s James’ passion that makes “Damn Your Eyes” a song about that regret that you sometimes enjoy sometimes.

2. Deer Tick, “The Dream’s in the Ditch”

For: The world you can’t escape

This is a restless song about a person that couldn’t get a good grip on their goals or dreams. It talks about a broad and general regret for the life you got stuck in. Frontman John McCauley hollers lines like, “Get over it kid, you don’t want any part of this” before arriving at the titular line, “the dream’s in the ditch.” But this version, with its simple two guitar acoustic setup and folkier vocals, makes for an easy listening soundtrack to regret.

3. Anderson East, “Find ‘Em, Fool ‘Em and Forget ‘Em”

For: The one you got too close to

This is a song with defiant bitterness. In it, a playboy father warns his song that the most efficient way to deal with women is, “find them, fool them, forget them” is. The singer doesn’t take this advice to heart and now he’s left with regrets from getting too emotionally attached. Yet, East’s voice has some blues tones with country inflection and a rock-and-roll swagger, which makes “Find ‘Em, Fool ‘Em and Forget ‘Em” less depressed. The song’s saxophone and trumpet add a certain flair, too.

4. Carolina Chocolate Drops, “I Truly Understand that You Love”

For: The one that moved on

Sometimes pain and regret needs to be expressed with panpipes and a banjo, and the Carolina Chocolate Drops do just that in this seemingly cheery old-timey tune. It’s an up-tempo jaunty song that serves as a sharp contrast to the bitterness of the singers’ sweet harmonizing voices. As chorus rolls on—”I truly understand that you love another man”—the whole song a delightful lament for the one that moved on.

5. Empty Houses, “Daydream”

For: The one you miss (who may not miss you)

Self-described as “Pop Soul Motown Indie,” Empty Houses has a song for the one you can’t quite forget just yet. Adam Mercer and David Mackinder bring a Casio keyboard and a light guitar riff to Ali Shea’s smooth vocals. She sings, “I would like to think you didn’t want to leave, it wasn’t only me.” She continues referencing a relationship that might be over, but the people involved aren’t over it. There are many fond and nostalgic odes to the possibly “rigged-game” nature of this relationship. She talks about crying all night, while trying to be “alright, living without it.” The song includes lots of “whoa-ohhs” for maximum catharsis.

6. Laura Gibson, “Empire Builder”

For: The one you lost (who didn’t get you)

Laura Gibson’s vulnerable voice and lightly plucked guitar help encapsulate a song about a relationship that that may have always been a little doomed. The narrator is a person who’s significant other didn’t seem to accept or understand why her “love songs were always the grieving kind.” Gibson sings, “hurry up and lose me, hurry up and find me again” but the song leaves her wandering through a deserted town looking for somebody that might have already left.

7. Christian Lee Hutson, “I Have to Keep You Down”

For: The one you hurt to keep

This song addresses a regret for doing all the wrong things to keep a relationship going. Christian Lee Hutson’s twangy voice is full of strained, pained, extended vowels and supported by a guitars, drums, a bass, a tambourine and some lightly harmonized vocals. Yet, Hutson fears that his lover will move on because she can do better than him. He tries to convince her otherwise, but apparently it didn’t work out so well.

8. Cavemen, “On My Own”

For: The one that left you on your own

Cavemen’s “On My Own,” is a song that regrets “the things that we once had,” that are now gone. This acoustic version is an easy-listening song of regret for loss and requests an old lover for another shot. The chorus repeats, “you don’t want me, I’ll be on my own” as the rest of song laments all the things “we once said.” The protagonist is asking for another shot, but unless that happens, he’ll just stay on his own.

9. The Heirs, “Lies”

For: Choosing to believe the lies

This song talks about an attachment to a person that says all the right things, even if they might not be true. This version of The Heirs’ “Lies” has Savannah Hudson singing and her brother Brandon on guitar and providing supporting vocals. She sings things like, “you tell me lies” and “you make it sound so good.” It’s maybe not the healthiest relationship, but it’s not easy to let go of the illusions. Savannah’s voice is breathy, but smooth as she returns to the line “I live for this, I live for you.”

10. Tommy Alexander, “Everyday Every Dime”

For: The life you can’t fix

This is a song for general and pervasive regret. This is the song for waking up in a funk that sticks around all day, leaving you twitchy and lost. Alexander’s voice is a solid alt-rock speak-sing and a lazy riff slips through the entire song. There are some vague references to a girl, and heavy imagery about passing lights and shadows that “scrape the ceiling.” The smooth drumbeat moves it along with an easy relentlessness in a way that seems to magically represent all of the small, nameless regrets.