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Broken Hearts Club: My Top 5 Heartbreak Songs

"She broke her wishbone and wished for a sign/I told her whispers in my heart were fine/What did she think she could do?/I feel for her, I really do"

This song was high school boyfriend heartbreak. A valiant, young, idealism gone typically wrong.I think it’s a mix between the Spandau Ballet sample and PM Dawn’s already-outdated lyrical flow that brought up nostalgia before I even knew there would be something to miss.

"He said, Rocky you met your match./Rocky said, “Doc it’s only a scratch,/and I’ll be better, I’ll be better, Doc, as soon as I am able.”

Rocky Racoon came to me during one of my many re-discoveries of The White Album while trying to process that awful pain of sorta-requited love in college. I was drawn to the foolishness of Rocky as I felt we had something in common. Years later, I read that Paul McCartney wrote this song on a roof in India as a jokey-cowboy song and couldn’t even keep the lyrics straight during recording--and I can’t even begin to tell you how that sums up this period of my life.

"Oh, I got a letter on a lonesome day/ It was from her ship a-sailin'/ Saying I don't know when I'll be comin' back again/ It depends on how I'm a-feelin'"

Thinking I came out unscathed of a particularly bad relationship when I moved back to the States after grad school, I was driving around DC and the first notes of Bob Dylan’s guitar reminded me so strongly of what I left that it caused that punch in the gut, that frog in the throat, and I became the girl in tears on I-495.

"She was oh so faithful. What a pitiful sight!/ Waited for the letter that you promised to write./ A gentleman with a top hat called around the other night,/And Annie doesn't live here anymore."

This one isn’t directed toward a person, but more of a place--places I’ve left--and a bit obvious because of my name. I have what one might call, “commitment issues,” and 25 different mailing addresses in the past 20 years and that’s not including several friends and family members who have put me up on their couches in between. Always trying to find the perfect place, never giving myself time to settle.

Most recently, I was living in a gorgeous old building in downtown Baltimore that gave me a leaky ceiling, a couple mice, a million roaches, and several bad heartbreaks ranging from super awkward OKCupid Dates to screaming matches. So, this is my general theme song when breaking up with a place that had so much potential, but ended up with water under your feet.

Yes, this song has been endlessly covered --but I stand by it. I am pretty loved-up in the romance department, but heartbreak is pretty sneaky and can take many forms outside of romantic love.

Sometimes old wounds flare up...sometimes plans don’t go as planned...sometimes you lose out on your dream job...sometimes babies aren’t born...sometimes depression is more than just getting fresh air...sometimes you get really sick...sometimes people you love get so sick that even though you are an atheist you start praying to god, any god, that will listen...sometimes you suffer the kind of loss of which has no real recovery, but instead a readjustment...

And when you need a reminder during any sort of heartbreak that you should cry, that you are not alone, that you can hold on...a sad song can medicate and let you meditate.

And if you are like me, it might even help to sing or hum along with the Late Leonard Cohen as he summed it up:

"And even though it all went wrong

I'll stand before the Lord of Song

With nothing on my tongue but Hallelujah"

Honorable Mentions

* Irreplaceable by Beyonce: A great reminder that life is ahead of you--not behind you, provides that kick-in-the-ass confidence you need after a break up, and... Beyonce, enough said.

* Ladies and Gentlemen We are Floating in Space by Spiritualized: This one was on repeat a lot in high school.

* I Can’t Make You Love Me if You Don’t by Bonnie Raitt: I think I was about 10 when this song came out, but damn, I felt it then and can still feel it now. Oh Bonnie, how I love thee...

* Tears by Yo La Tengo: In college I had this on repeat in my ‘92-dodge-caravan with fake wood paneling and a mismatched trunk that leaked antifreeze all over Baltimore, but that emo-metaphor is for another day, another song.


Are you a fellow lover of sad songs?

Although I have been a professional writer for more than a decade, I only wrote my first song three years ago. And it was sad.

I needed to start performing, cutting my teeth at open mics, but every time I considered getting on the list I thought, “man, no one is going to want to hear this downer!”

But I wasn’t alone. All artists (and humans) are trying to process the “un-processable,” and for some, that’s a sad song.

I started talking to local musicians in the area and an opportunity at Motor House from QueenEarth was presented to me, so I had to jump on it. And the Broken Hearts Club was born. We are blessed by the following musicians to share their favorite sad songs:

* QueenEarth whose song “You Never Came for Me” brought me to tears when I first heard it.

* Alex Alexander whose raw, authentic voice and poetry has had me in awe since the first time I saw her perform.

* Scotty P. whose voice and songwriting skills are are reminiscent of the greats.

* Teporah whose piano and voice remind me of all the powerful women who have sang to my soul.

* 4TAE whose soul/jazz arrangements taught this writer that it’s not all about the lyrics, sometimes the right chord can touch you deeper than a word ever could.

And now, I want to hear you.

Join us at the Broken Hearts Club Open Mic and share a sad song, poem, story, or maybe just a hilariously bad Tinder Date.

Date: Feb 16, 2019

Time: 8 - 11pm

Where: Motorhouse

If you or someone you know is suffering from depression or has contemplated or is contemplating suicide, please contact the National Suicide Prevention lifeline at 1-800-273-8255. Available 24 hours a day.



Annie Cassidy is a singer/songwriter in Baltimore, MD. Her debut EP, False Royalties is available on iTunes, Amazon, and all streaming sites.

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