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The Big Smoke’s Ultimate Feels Playlist: Heartbreak, Heartache, Breakups, and Sass

Have a broken heart? Been betrayed? It’s okay, there is an app for that (no, really), but most importantly there are a plethora of amazing tunes that back up all your feels. The Big Smoke counts down the 21 best songs to help heal a broken heart whatever stage you are at. (No Taylor Swift or Adele here.)

Some annoying people at The Big Smoke have felt the need to add their go-to songs, but I have requested they don’t hijack my heartbreak—this is the better playlist. (Click here to stream the entire playlist.)

The first half of this list is feeling sorry for yourself, but then it moves into the second phase of accepting it (unhappily), to the final stage of being able to let it go and move forward. What is your go-to song? Comment below!


1. Etta James, “I’d Rather Go Blind”

“Something deep down in my soul said, ‘cry, girl,’ when I saw you and that girl walking by / I would rather go blind, boy, than to see you walk away from me”

The ultimate song of heartbreak, Etta James sings with absolute disbelief and pain at watching the man she loves decide to be with someone else. Beyonce did a lackluster version, but she has Jay-Z and has no right to get involved in this conversation right now. We understand this song is not a politically correct pick, etc. … #dontcarejustshare


2. Otis Redding, “I’ve Been Loving You Too Long”

“My love is growing strong now, as you become a habit to me / I’ve been loving you oh too long, I don’t want to stop now”

This song is an absolute chilling version of a song about having to let go when you realize that the other person does not care at all. It’s a killer, but Otis emodies the back and forth one goes through when they realize they have to move on.


3. Justin Timberlake and Chris Stapleton, “Drink You Away”

The bottom of the bottle, to fill this empty heart up, a thousand proof don’t change the truth / I can’t drink you away, I’ve tried Jack I’ve tried Gin I’ve tried all of their friends”

Ugh. I know, Justin, right? I can’t even pretend to care right now that it’s by the guy who wore double denim with Britney Spears back in 2001. I actually first heard this song when Justin performed it live with Chris Stapleton at the Country Music Awards in 2015—but this song delivers when nothing you drink removes the person from your brain.


4. Nicole Scherzinger, “Run”

“You try and try and try, but he’ll just shut you down / Don’t wanna say I told you so—so please, go now, run!”

This is even worse than Justin because it’s an ex-Pussycat Doll. But this song is amazing and is basically an example that sometimes when you see someone for who they are and discover nothing you believed about them or your relationship was true, you wish you had been warned to run. (Side Note: Often you are warned somehow to run but you ignored it.)


5. Traveling Wilburys, “Congratulations”

“Congratulations, you got a good deal, how good you must feel / I guess I must have loved you more than I ever knew, my world is empty now ’cos I don’t have you / And if I had just one more chance to win your heart again, I would do things differently but what’s the use to pretend”

When most people reference a heartbroken Bob Dylan song, they focus on “Don’t Think Twice, It’s All Right.” While an amazing song, I think “Congratulations” is completely underrated and a perfect song to go out in a bittersweet fashion to the person who didn’t know when to stop.


6. The Weeknd, “Wicked Games”

“Bring your love, baby, I can bring my shame, bring the drugs, baby, I can bring my pain / I got my heart right here, I got my scars right here / Tell me you love me, even though you don’t love me / I give you all of me, even though you don’t love me”

That moment when you don’t have the guts to let the person who loves you go, because you want to keep them on the line. My YouTube-psychology training tells me this is a process nearly everyone goes through at some point in their lives, hurting people because of our own pain and our inability to get past certain truths.


7. Smokey Robinson and The Miracles, “You Really Got a Hold On Me”

“I don’t want you, but I need you / Don’t want to kiss you, but I need to / Oh, you do me wrong now, my love is strong now you really got a hold on me”

In the same vein as Otis Redding’s song I mentioned, this is one of those songs when you absolutely know the person you adore is messing with you and you don’t want to be in this weird cyclical relationship and you want to “split now, but you can’t quite now.” We get it, but Scherzinger it and run—they won’t change.


8. Miranda Lambert, “Mama’s Broken Heart”

“I cut my bangs with some rusty kitchen scissors / I screamed his name till the neighbors called the cops / I numb the pain at the expense of my liver / Wish I could be just a little bit less dramatic like a Kennedy when Camelot went down in the flames”

A bit country for my normal tastes, but a fabulous example of when you have a broken heart but everyone is trying to tell you to keep it together. Sometimes you not only can’t, but simply don’t want to … for a while. Also, your mom is pissed off you are being so dramatic, so get on with it.


9. The Beatles, “I’m So Tired”

“I’m so tired, I don’t know what to do / I’m so tired, my mind is set on you / I wonder should I call you but I know what you would do / You’d say I’m putting you on, but it’s no joke it’s doing me harm / You know I can’t sleep, I can’t stop my brain, you know it’s three weeks / I’m going insane!”

Essentially, this song is about the expected and inevitable onset of insomnia that comes from heartache, where every waking moment is spent agonizing over what went wrong and you try to understand everything they said when it’s so at odds with what they did. You can’t and you likely will never understand why.


10. Peggy Lee, “Black Coffee” 

“Black coffee / Feeling low as the ground, it’s driving me crazy this waiting for my baby to maybe come around”

While we don’t abide a woman having the role of “waiting around for a man” and “tending her oven while she frets,” we do appreciate the context of when this song was produced and how it embodies the frustration and heaviness of hoping he comes back after spending weeks not sleeping, drinking coffee, and smoking cigarettes.


11. Randy Crawford, “When I Get Over You”

“There will be a moral to this story, when I get over you / I will be the life of the party, I will misbehave and act the fool, and I won’t care who knows me when I get over you”

I love the haunting way Randy Crawford sings this song, it’s almost like a sad girl sitting in a bedroom staring at the wall, heartbroken, but realizing things will get better. It’s not a particularly powerful ballad, but there is something magical in the listless hope.


12. Billy Joel, “And So It Goes”

And so it goes, and so it goes, and so will you soon, I suppose / So it goes, and so it goes, and you’re the only one who knows / So I will choose to be with you, that’s if the choice was mine to make, but you can make decisions too and you can have this heart to break

Billy Joel at his finest, with the tale of the total heart-wrenching, soul-destroying acceptance that the person you would choose to be with over everyone else is choosing someone else … and so it goes.


13. My Morning Jacket and Erykah Badu, “Tyrone”

“I just want it to be, you and me like it used to be / But you don’t know how to act / So, as a matter of fact, you better call Tyrone and tell him to come and help you get your shit / but you can’t use my phone”

The sassy Erykah, no one is messing around with her, okay? I love this version of “Tyrone,” because it’s with one of the best and most underrated bands, My Morning Jacket. The song is about that point where you are tired of their shit and suggest they go call their friends instead of wasting your time.


14. Mary J. Blige, “Not Gon’ Cry”

“I’m not gon’ cry, no I’m not gon’ cry, it’s not the time, I’m not gon’ shed no tears, it’s not the time, ’cos you’re not worth my tears”

This version was when Mary J. Blige performed with Eric Clapton. It was on the soundtrack of the ultimate breakup movie, Waiting to Exhale. It’s that moment when you are like, “You know what? This sucks!” They suck and they aren’t choosing you, so you are not wasting any more time. Props to Clapton in this performance.


15. Tom Waits, “Bad Liver and a Broken Heart”

Well, I ended up with a bad liver and a broken heart / Yeah, I drunk me a river ever since we’ve been apart / I wish you’d have known her, ’cos we were quite a pair / So welcome to the continuing saga, she was my better half”

Tom Waits totally is the person you want to sit next to in a bar, drinking a whiskey and talking about how you’ve been ditched. This song is the epitome of a drunk guy reminiscing but won’t bother chasing her and ends up with a bad liver and a broken heart.


16. Bette Midler, “Is That All There Is?”

“I fell in love with the most wonderful boy in the world / Then one day he went away, and I thought I’d die, but I didn’t, and when I didn’t I said to myself, ‘Is that all there is to love?'”

Peggy Lee did a marvelous job on this song, but I love Bette Midler’s clarity and matter of fact-ness without complete despair when singing, “Is that all there is to love?”


17. Marion Cotillard, “Take It All”

“Now it’s your turn, to finally learn / You had the world, you had your fling, you wanted more than everything, you got your wish, you got your prize / You grabbed for everything, but don’t you see that in the end, there will be nothing / Left of me”

From the adaptation of Frederico Fellini’s 8 1/2, this song is performed by actress Marion Cotillard in the film Nine which was a bit of a flop, but this song is epic. The song is when the cheating Guido Contini’s long-suffering wife says, “Thank you for reminding me I’m not special. … You’re just an appetite. … You take everything and I’m empty.”


18. Dashboard Confessional, “Rapid Hope Loss”

“Do what you must if that’s what you wish, I can’t be a party to this, you have sense that you were born with, you find a way to make things right, I guess that all you got is all you’re gonna get”

This is one of those emo songs by a lead singer who is unlikely to have any real chick problems considering how many women scream out his name at every concert. Alas, the song does lend to the point where you get why the other person won’t deal with what’s happening between the two of you. For some, it’s easier to avoid and not respond—so now they’re gone and their endearing sense of charm is wasted on you.


19. Wynonna Judd, “That Was Yesterday”

And so it goes, another lesson gets learned / And in the big book of experience, another page gets turned / Now you say you need me—well, Honey, you got some nerve / I hope some sweet tomorrow, we both get what we deserve

This song is absolute fierceness. I don’t even need to write an intro for it, way more fierce than any “Eminem is angry at Kim” song out there …


20. A Great Big World, “Land of Opportunity”

“I’m running away to a place where you won’t bother me, we won’t talk for a while we’ll be okay / I wasted my time, I missed all the signs / I want you to know, I had to let go / I just gotta believe there is something better, I just gotta believe there’s something more than you and me”

This is that great song when you realize that you cannot maintain a friendship with the person who broke your heart, it’s not feasible and there will be too much pain—at least for now. It’s that glimmer of hope that maybe somewhere there is someone else you will like as much if not more than them!


21. Blue October, “Breakfast After Ten”

So just pick your head up, boy, and walk away, walk the coolest walk that you know / ’Cos in a month or two she’ll call you, you gotta hang up the phone / And I’ve learned a lot from all these break ups and make ups and fuck ups and fake outs, things that I wish you could comprehend / But for now I’ll lace up these wingtip shoes, boys, and I’ll go and have breakfast with my good friends”

Everyone always plays Gloria Gaynor’s “I Will Survive,” but really “Breakfast After Ten” is where it’s at. This song is all about that moment when you realize actually, this is not about you, this is their shit. Sometimes you just have to hang up the phone because they will never change or care.


What is your go-to song? Comment below!




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