Many Shades of Parting – My Favorite Breakup Songs

People are afraid of themselves, of their own reality; their feelings most of all. People talk about how great love is, but that's bullshit. Love hurts. Feelings are disturbing. People are taught that pain is evil and dangerous. How can they deal with love if they're afraid to feel? Pain is meant to wake us up. People try to hide their pain. But they're wrong. Pain is something to carry, like a radio. You feel your strength in the experience of pain. It's all in how you carry it. – Jim Morrison

Mi gran amigo and fellow blogscribe, Justin, told me he was writing a list of his favorite breakup songs for Valentine’s Day. I wanted in on the action. Life is full of pain, and what good is it keeping it to yourself? Plus, back when I lived in San Francisco, my Casa 909 household had an outstanding Valentine’s tradition that I still miss; we used to watch cheesy-gory horror flicks, get sauced on vino and heckle the moronic characters behind the television screen, especially when the killer was about to slay a couple of dumb teenagers in the throes of lovemaking. This was great for raucous laughter. Those were the coolest Valentine’s Days I’ve had so I thought this counter-lovey-dovey exercise could be fun, too.


Before I leap into my list, here are my honorable mentions: Si Vos Te Vas by Piero: I love how gracious, emotionally mature, and borderline cheerful this ditty is; a rarity for a breakup song. Most Likely You'll Go Your Way And I'll Go Mine by Bob Dylan: what’s a list of great breakup songs without one from Bobby D? Although I’m not versed in his lengthy catalog, I love how calmly brash this song is. The fuck-you-and-good-luck-to-you sentiment has always been palatable for me. Dionne Warwick’s rendition of Walk On By made my cut because it’s such a catchy song. Warwick’s voice is so sweet it makes the lyrics even more heartbreaking. And finally, Journey’s Separate Ways (Worlds Apart) makes my honorable mentions because ① it’s a fucking awesome song!, ② it helped to get me laid on a first date (San Francisco’s dating scene is good for that), and ③ Steve Perry’s lyrics are kind of amazing; “Separate Ways” is a breakup song that expresses sentiments like “If you must go, I wish you love.” Wtf? That’s great, man! Steve Perry is a rock ‘n’ roll Jesus! And the music video’s so cheesy it’s fucking cool:



If you’re a sucker for exquisite breakup songs like I am, check out my homeboy’s list here. Here are some of my favorite disgustingly sad songs that have helped me get on my feet when my heart’s been broken (like Justin, cheery songs have never made me happy when my spirit’s in tatters, but drowning in my sorrow by listening to sad music has been my way of diluting it from my system), and some songs that awaken those depressing moments from my life:  

The One I Love – R.E.M.


Within this musical genre a palette of distressing human emotions are evoked: disillusionment, pleading, despair, dumb hope, defiance, and good old suffering. Since we’re in the realm of suffering, anger can’t be too far (or as Yoda once said: “Anger leads to hate. Hate leads to suffering.”) Enter R.E.M.’s “The One I Love.” Although I humbly believe my breakup mix is littered with superb songs, this one’s probably my favorite. How could I not love a song that opens with this deliciously vicious verse:

This one goes out to the one I love 
This one goes out to the one I've left behind 
A simple prop, to occupy my time 

“The One I Love” is my favorite fuck-you breakup song. So simple, so direct, so mean. And it scores extra points since I’ve read that fans who paid to attend a R.E.M. concert—meaning they should be people who are familiar with their music—would slow dance to it because they mistook it for an I-love-you song. (They’re probably also the same impoverished white folks who vote for Republicans.)  

Dreams – Fleetwood Mac


What good would a list of outstanding breakup songs be without one from Fleetwood Mac, let alone without a selection from Rumours, one of the penultimate breakup albums? Of all the songs I mention on this list “Dreams” is the one I listen to the most. "Players only love you when they’re playing" is such a delicious line especially when you consider that Lindsey Buckingham had to play and listen to Stevie Nicks and Christine McVie sing those lyrics. I’ve also always been fond of the sentiment Stevie conveys when she sings "When the rains washes you clean you’ll know." Without question, “Dreams” would be my pick for most beauteous fuck-you song ever.

If You Leave Me Now – Chicago 
In my late twenties I had a blink of a relationship with an ex-coworker named Victoria. One afternoon, we strolled into a restaurant on 24th Street in the Mission. While we waited for our order, this song played. I’m a big slut for soft rock classics so I couldn’t stop smiling while we listened to it. I think I began to croon the “Ooooh no, baby please don’t go” part. We got a kick out of it. And so, although this song is a total breakup song, it informally became our song. In retrospect, that was a huge red flag but it kind of fit since weeks after we began dating I left to wander around South America for two months on a trip I had already planned. Once I returned, we had some fun moments but we also had way too many ridiculous fights because we were both fiery, stubborn people. And so, our song fulfilled its inherent promise.

But I still think it’s a purty song.  

Pero Te Extraño – José José
What would a list of my favorite breakup songs be without one from José José, one of my favorite singers? The saxophone and piano notes sprinkled here and there give the song a loungy feel. The dramatic strings manage to match the emotional heights José José is able to hit in this song. In his youth, at his peak, his voice was simply unmatched. Starting from the 1:25 mark to the end of the song: dear god. No words. It still makes me tear up not because I feel that sadness in the moment but because there will always be a part of me that cannot comprehend how a human being can sing with such emotion and gorgeosity.


Maybe I’m an overly dramatic motherfucker (I suspect so), but this song has always felt peerless in conveying that pure sorrow one feels from a broken heart. If they sold this song as a twelve-inch single, they should have included a small pack of Kleenex to accompany it.

After the Love Has Gone – Earth, Wind and Fire 

Something happened along the way 
What used to be happy was sad 
Something happened along the way 
And yesterday was all we had 

Of all the songs on my list, “After the Love Has Gone” has my favorite lyrics. Every breakup is unique but a big reason why every heartbreak hurts so much is because of the joy that preceded it. The pain of losing a love is amplified because it is all too easy to remember the good times, and to wonder where it all went wrong. This song captures that like few others that I know.

My World is Empty Without You – The Supremes 
 I’ve always loved the intro—how earnest and serious the bass, organ, and drums sound before they give it over to Diana Ross and a beat conducive for defiant dancing. The instrumentation and super-subtle backing vocals provide a perfect backdrop for peak-Diana and her anguished, desperate vocals. The lyrics are so frank and simple; it’s classic, textbook Motown. A few samplings include: And as I go my way alone/I find it hard for me to carry on, or From this old world I try to hide my face/From this loneliness there's no hiding place.

Yup, that’s heartbreak.

I Wonder (Where Are You Tonight) – Aretha Franklin 
For the longest time I never saw what the big deal was about Aretha. I was familiar with her classics like “Chain of Fools” and “Respect” but she didn’t seem that amazing. I understood once an old roommate of mine started playing Aretha Sings the Blues in our kitchen. Man, Aretha was really good, and this is my favorite song on the album. It’s a sparse composition which allows Aretha’s ridiculously beautiful voice to rightfully have the sonic spotlight.  

Crazy – Patsy Cline

Before I turned thirty I used to be absolutely crazy for an ex coworker of mine who had a long-time boyfriend. (It was the only time I’ve been involved in an affair.) On weeknights we drank hard at bars throughout San Francisco. Club 93, a dive bar in SOMA I’ve written about before, was our spot. The bar attracted few patrons so we oftentimes hogged their gem of a jukebox. We hit that bar enough times that one night I became adventurous with my jukebox selections and picked a song from their Patsy Cline disc. I was tipsy at that point but not blackout drunk like I occasionally got on our nights together. I remember sitting on my stool beside The Woman Who Had an Affair With Me and marveling at how perfect the song was for us, particularly the lyrics I'm crazy for trying / And crazy for crying / And I'm crazy for loving you. I even told her it perfectly summed us up! She grinned in agreement. Even then, I must have known that our illicit relationship would fizzle, that she would never leave him for me, but I didn’t want to stop my love for her: her sardonic humor, her kiddie smile, and her midwestern inflection when she said words like “crabby pants,” “douchebag,” or “For Christsakes!”

Since we went our inevitable ways, I’ve discovered more of Patsy’s songs but “Crazy” will always remind me of her.

Broken Heart - Spiritualized
Although I hardly ever listen to it, I think this song is astounding. It feels like a song that should be listened to while high (like the rest of the album), but, at the same time, a song that perfectly encapsulates the all-consuming, all-encompassing veil of numbness that comes from having a broken heart. Can music get sadder than this? In my book: no.

And the lyrics are so precise it’s heartbreaking. The love we have for another is a dream. A broken heart is symptomatic of a broken dream and few things hurt more than feeling it shatter. And I know I’ve been here:

And I'm crying all the time 
I have to keep it covered up with a smile 
And I'll keep on moving on for a while 
Lord I have a broken heart  

Lost Cause – Beck


Here I was, sitting at my writing desk, giving this song a good listen with my headphones when my wife—my sweetheart, mi tesora, the love of my life—strolled in. I still looked at her with this wounded look, and I still felt like I could tear up listening to this song. Yup, this one still cuts deep. And it should. Sea Change was Beck’s breakup album. (Beck recorded the album after his breakup with his longtime girlfriend.) I hardly listen to the album; it’s a real wrist-slasher. Although I’m far more apt to listen to “The Golden Age,” “Guess I’m Doing Fine,” or “It’s All in Your Mind” when I’m feeling empty and blue, this song has always been the one I’ve identified with the most when I was trudging through a breakup (like my last one). Beck’s lyrics, his numb, defeated monotone, are just devastating. And I think many of us have been here at one point or another in our lives:

I’m tired of fighting 
Tired of fighting 
Fighting for a lost cause.  

Against All Odds – Phil Collins
Here’s a true story: I once included this song in a mix I made for my last ex-girlfriend, Blanca. At the time, we were on one of our many rebounds. I thought there was still some hope that we could right our love boat, but a good friend of mine told me this song should never be part of music mix for a good relationship. And she was ultimately right.

It would be an understatement to say that we had a tumultuous relationship. I wasn’t my best version for her. At that critical juncture in my life, I wasn’t in a position to give her my best. Early on in our relationship I was a horrible partner. I used to carry a lot of regret about that. Shit, it’s probably still buried inside me somewhere. In some ways I recovered after our first act, became a better partner, but by then it was too late to save our dream although that didn’t stop us from clinging on far longer than we should have. This song captures all that for me—which is why I never listen to it.

 

Still Loving You – The Scorpions
The greatest power ballad ever? Of course, that’s completely subjective, but it would be my choice. It’s such a quintessential breakup song: super-emotional to the point of being operatic; an incredible vocal performance (Klaus Meine ist die Scheiße!); brimming with longing, regret, and suffering (If we'd go again / All the way from the start / I would try to change / The things that killed our love, or the song’s peak when Meine shouts “I’m still loving you”), and it scores a fucking ten on the emotionally cathartic chorus scale.