My Top 10 Breakup Songs

Breaking up with someone is one of the worst experiences we have in life. Truth be told, the only thing that’s worse is having someone close to you die, and even that pain comes from a similar place: the pain in your heart you get from the knowledge that you’re being left behind, that you’re not going to see a person you cared about anymore, that she (or he) is out of your life.

It’s a horrible feeling, and it’s also a feeling that almost everyone experiences at some point. Of course, the universality of the experience doesn’t make it any easier. You can know that everyone has felt as low as you do. You can tell yourself that eventually the misery will pass. You can tell yourself that you’ll meet someone else, that the person you just broke up with wasn’t the answer to all your problems (as if anybody could be that). But intellectually knowing those things won’t stop you from feeling like your chest was sliced open with a razor blade and your heart was pulled out and chucked against the wall like a piece of worthless dead meat.

When you feel like this, there’s only one thing that helps: ALCOHOL!!!

So many sorrows drowned

So many sorrows drowned

Except not really. The more you try to drown your sorrows, the better those motherfuckers learn how to swim. (Mine are basically Michael Phelps at this point.) So if getting drunk doesn’t help, what does? For my money, there’s only one medicine for heartbreak. Not a cure, mind you, just a treatment. Of course, I’m talking about music. And not just any music. I’m talking about my favorite kind of song, what I like to call the “miserable suffering bastard” song.

It’s no surprise that I say this, I’m sure. I’ve long been a lover of sad songs. Even when I’m in a good mood, you’ll usually catch me singing along to something in a minor key. The sadder a tune is, the more suicidal the singer sounds, the more likely you’ll find that song on one of my playlists. And when I’m going through a breakup, I dive all the way to the bottom of the ocean. I’ve written this before, but when I’m really sad, listening to a happy song doesn’t help. It just makes me more upset. But listening to a sad song is soothing. A sad song rings through you, tells every bit of you that you’re not alone in your pain, no matter how lonely you may feel, that someone else out there understands you. Even the most awfully depressing song, in a way, makes me feel that eventually things will be okay.

With Valentine’s Day coming up this week, I thought I’d put together my Top 10 breakup songs, the ones that best capture how I feel at the end of a relationship, that help me get through to the next day. (And I’m not alone. My fellow blogsmith Juan Alvarado did his list as well.) So for all you lonely lovers out there, if you’re stinging from your last breakup, or if you just feel like getting drunk and listening to some sad songs because you’re a miserable suffering bastard … this list’s for you. Lie on your bed, stare at the ceiling … and play it loud.

Honorable Mentions: The Beatles’ Yesterday is certainly the most famous breakup song ever written, and if I had written this list five or ten years ago, it would have cracked the top five. But I have to be honest, when I go through a breakup, it never cracks my playlists anymore … This whole list could just be Fleetwood Mac’s epic album Rumours. In particular, I love Silver Springs, mostly for the completely psychotic way that Stevie Nicks stares at Lindsey Buckingham while she sings it in The Dance. But I think my problem with using any of these songs as true breakup music is that, even though the topics are depressing, the music itself is pretty upbeat. When you listen to Never Going Back Again, you don’t think, “Wow, that girl must have been a bitch”; you think “Damn, that is some awesome guitar picking.” Maybe that’s just me, but that’s why there’s no Fleetwood Mac on the list … Same thing goes for Smokey Robinson’s The Tracks of My Tears, which is lyrically sad but so musically joyful … If you haven’t listened to Frank Turner’s The Way I Tend to Be, go do so right now (or at least after you read the rest of this post) … And there’s an obscure country song called Ain’t No Ash Will Burn that I learned from my friends Izzy and Brenda, an adorable elderly couple of musicians who I met at Sunny’s in Brooklyn and who sing, in gorgeous harmony, “Love is a precious thing I’m told/Burns just like West Virgina coal/But when the fire dies out it’s cold/There ain’t no ash will burn.” The best version I’ve found on the Internet is this one, sung by Josh Oliver and Jill Andrews of the everybodyfields (who will be coming back later in the countdown).

I sing this to myself pretty much everyday—but it didn’t quite make the Top 10. Ready for some more heartache? Let’s get to it.

10. You Don’t Know How It Feels, Tom Petty

Petty’s Wildflowers is yet another great breakup album, a record from which you could pick any number of songs to listen to when you’re down. (I can’t tell you how many times I’ve listened to Crawling Back to You.) But there’s something I particularly love about this one: Like I said above, we all know what it feels like to have our hearts broken. But even knowing that, when we’re actually going through the painful process of shattering and then trying to pick up the pieces, when we’re in that “I’m too alone to be proud” phase, you can’t help but think that nobody can relate to how bad you feel. We all have the thought: “You don’t know how it feels … to be me.” But the truth is, everyone knows how it feels—including (maybe especially) Tom Petty.

9. Horseshoe Lounge, Slaid Cleaves

You know what’s the worst? Running into an ex in a public place. Especially if you’re in a situation where you have to interact. And especially if you’re not over that person. Slaid Cleaves captures that feeling in the great song Horseshoe Lounge, which is set in and named after a real bar in Austin, Texas.

Of course I've been there

Of course I’ve been there

Cleaves describes going to the bar with a buddy for cigarettes, whiskey, and a few games of pool. He sees his ex at the bar, dancing with her new man, and he can’t do anything about it but “Peel the label off a Miller Lite” and “Pull hard on the sorrow and smoke.”

That helpless feeling of seeing somebody and knowing you shared something, and that you still have feelings for her, and that you wish you could give it another try, but you can’t? Oh yeah, been there.

8. Your Time Is Gonna Come, Led Zeppelin

You can’t have a breakup songs list without something to listen to during the angry, fuck-that-fucking-bitch phase, right? Well, choice lyrics from this track from Zeppelin’s first album include “Lying, cheating, hurting, that’s all you seem to do”; “One of these days and it won’t be long, you’ll look for me but baby, I’ll be gone”; and “Don’t care what you say/Cause I’m going away to stay/Gonna make you pay for that great big hole in my heart.” It’s not exactly subtle, and you could probably argue that it’s misogynistic (like a lot of the Zeppelin catalog…), but fuck it; when you’re pissed, you’re pissed. And the last minute of the song, when Plant chants “Your time is gonna come” while Page shreds on the pedal steel guitar and Bonham beats the shit out of the drums—is just sublimely cathartic.

7. Buckets of Rain, Bob Dylan

Bob Dylan released Blood on the Tracks in 1975, shortly after getting divorced from his longtime wife, Sara.


It’s one of his finest albums, and many consider it the greatest breakup record of all time—like with Rumours, I could have just written out the album track listing here and had a fine countdown: Tangled Up in Blue, Idiot Wind, If You See Her, Say Hello, You’re Gonna Make Me Lonesome When You Go … just on and on. I can’t tell you how many times I’ve laid in my bed and listened to this album on repeat—Tangled Up in Blue especially. But I think my favorite is the bittersweet Buckets of Rain. Most of the songs on this list are about post-breakup grief, but Buckets of Rain is about that time before the split actually happens, when you still love someone but you can see the cracks are beginning to split wider, and you can tell that pretty soon it’s all going to bust apart whether you want it to or not. There are two verses in particular, that I love and that sum up the feeling: “I like the smile in your fingertips/ I like the way that you move your hips/I like the cool way you look at me/Everything about you is bringing me misery;” and the last verse, “Life is sad/Life is a bust/All you can do is do what you must/You do what you must do and you do it well/I do it for you, honey baby can’t you tell.” Bittersweet indeed.

Also, while I love Dylan’s version of it, there’s a cover that I’ve been listening to lately that’s just amazing. Check out Beth Orton and M. Ward.

6. Drown In My Own Tears, Ray Charles

This song would be on the list just for the power of “The Genius” singing “It brings a tear into my eyes/When I begin to realize/I cried so much, since you’ve been gone/I guess I’ll drown in my own tears.” But what really makes it so beautiful and powerful is the moment near the end of the song when the Raelettes come in with a harmonized “Drown in my own tears.” Their voices just crash into you with a crescendo of sorrow that makes you really feel as if you’re going to drown in tears.

5. See You Later, Elliott Smith

Any catalog of music to listen to when you’re bummed out (as well as any Top 10 list I ever write) is bound to have an Elliott tune or two on it. Smtih seemed to spend most of his life breaking up with life, so he’s got all sorts of great breakup songs (Say Yes, I Didn’t Understand, Easy Way Out, Pitseleh—oh god, Pitseleh), but my favorite is one that he recorded with Heatmiser, before his solo career started. See You Later opens with one of the great lines about drowning your post-breakup sorrows: “I got a choke chain, made out of Night Train/To keep your memory down.” And his voice on the chorus when he sings “See you later, if I see you at all,” is so piercing, so full of pain. So perfect.

4. The Wind Cries Mary, Jimi Hendrix

As I wrote when I did my Top 10 Hendrix songs a few weeks ago, this song always ends up spinning on repeat when I go through a breakup. Jimi so beautifully captures the melancholy feeling that comes when a relationship dissolves, the feeling that you’ve lost your best shot at love, or the best love you’re ever going to have, and that you’ll never find another: “Will the wind ever remember/The names it has blown in the past?/And with its crutch, its old age and its wisdom/It whispers no, this will be the last.”

He may have been only 24 when he wrote this, but Jimi knew how the end of something can make anyone feel as old as the wind. I think that’s even more true for those of us who were born with old souls.

3. Fucked Me Right Up, Sean Hayes

I first saw Sean Hayes eight or nine years ago at the Makeout Room in San Francisco. The room was mostly empty, and I’d never heard of him—I think I was there to see someone else on the bill. But Hayes got on the stage with a guitar and sang this song in his croaky voice, sang “Don’t know that she knows what it is she’s doing/Don’t know that she knows how deep this will cut/I can’t believe you really think we’ll make it through this/Oh you fucked me right up/Just fucked me right up.”

I had a girlfriend at the time, but this song went right into the rotation. I knew I’d need it someday. It turns out there have been a lot of days I’ve needed it.

2. Wasted Time/Everything Is Okay, the everybodyfields

The everybodyfields were a great alt-country band that dissolved when singer/songwriters Jill Andrews and Sam Quinn broke up. Wasted Time and Everything Is Okay are technically two songs from their third and final album, Nothing Is Okay, but they ran them together on the album and in live performances, so I count them as one. These songs remind me of a story I’m not sure I should tell, but here we are: I was once in a relationship that lasted six years—the better part of my twenties. We grew dependent on each other, as you’d expect, but she was particularly dependent on me because she had serious health problems. (She died a little more than a year after we broke up). One night, maybe two months after we had split up and moved out of the apartment we shared, I got  a call from her. She was low, needed someone to talk to, and didn’t know who else to turn to. To this day, every time I hear Andrews sing “Hey, it’s me/I know it’s 3 a.m./I’m begging please/I’m all alone and need a friend,” I think of the moment I saw my ex’s name on the caller ID.

We spent three hours on the phone that night. She was in tears for most of it. There wasn’t much I could do except tell her that “everything was okay,” like Andrews sings, even though we both knew it wasn’t. That remains one of the most painful nights of my entire life, one that I wouldn’t think anyone could understand—and yet the everybodyfields are right there with me.

1. Call Me On Your Way Back Home, Ryan Adams

Because it’s on my favorite album, which is also my favorite breakup album. Because that album is called Heartbreaker. Because when I went through my worst breakup ever, this was the only song I listened to for weeks. Because “I just wanna die without you … Honey, I ain’t nothing new.” And because the harmonica solo at 2:25 makes the exact sound of a heart breaking.

I have to admit, compiling this list took me to a pretty dark place. But at the same time, looking over it now, and listening to it as a playlist, it makes me feel just a tiny bit better. I hope it does the same for you.

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2 Responses to My Top 10 Breakup Songs

  1. Pingback: My Top 10 Ryan Adams Songs | From a Brooklyn Basement

  2. Pingback: My Top 10 Favorite Beatles Songs | From a Brooklyn Basement

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