14 brutally sad – yet fantastic- songs for Valentine’s Day

Charles M. Schulz got it right with this 1967 gem of a book which, thanks to a yard sale a couple of years ago, I am the proud owner of. It’s true. Happiness IS a sad freakin’ song, especially one that is well written and sung with just the right amount of desperation and sincerity.

happiness-is-a-sad-song-book

I don’t mean songs like Erin Carmen’s “All By Myself” (with all due respect). I’m talking about ones a bit off the mainstream path that pack way more of an emotional punch for this gal.

So in honor or the 14th of February, let’s celebrate Valentine’s Day with this collection of 14 brutally sad yet outstanding songs about love, the human heart and the various forms of related suffering.

Ready? Set? Heartbreak!

ONE: “1000 Oceans” by Tori Amos. Gorgeous. Absolutely gorgeous. But my oh my.

 

TWO: “Somebody” by Depeche Mode. For no other reason than the longing in Martin Gore’s voice. This song has been making me feel all the things for decades.

 

THREE: “I Know It’s Over” by The Smiths. Frankly, Mr. Shankly, I don’t think this one needs an explanation. And let’s be honest, this entire post could be ALL Smiths songs. God I love them. Oh well…enough said.

 

FOUR: “The Power of Love” by Frankie Goes To Hollywood. This song slays me. It’s not specifically “sad” but just so overwhelmingly powerful and emotional. Frankie say tears! p.s. listen to the song with your eyes closed. The video’s kinda nutty. “Love is like an energy…rushing inside of me”

 

FIVE: “The Blower’s Daughter” by Damien Rice. There is literally nothing I can say about this. Nothing.

 

SIX: “Never Be Mine” by Kate Bush. She’s a goddess. This song’s insane. Meaning perfect.

 

SEVEN: “This Year’s Love” by David Gray. Because “when you kiss me on that midnight street, sweep me off my feet” is one of the greatest lines ever written. Oh and the entire song will rip your heart out.

 

EIGHT: “A Soft Place to Land” by Kathleen Edwards. Kathleen Edwards is one of my reasons for living. This song. The violin, the words. All of it. Take a whole lot of deep breaths before listening to this extra amazing live version.

 

NINE: “You Left It Up To Me” by Indigo Girls. Achingly sad and therefore I love it  And the harmonies are really great.

 

TEN: “The Last Day of Our Acquaintance” by Sinead O’Connor. This one will rip you apart at the seams but will also remind you of HOW SPECTACULAR Sinead is.Extra great live version for added Sinead bliss.

 

ELEVEN: “That Wasn’t Me” by Brandi Carlile. If you know it then you probably already love it and if it’s your first time hearing it then get ready to have the wind knocked out of you.

 

TWELVE: “I Can’t Make You Love Me” by Bonnie Raitt. Excruciating. But I’ve also heard it entirely too many times so it doesn’t kill me nearly as much as it used to.

 

THIRTEEN: “Crying” by KD Lang. I know, I know. It’s a Roy Orbison classic. But this one kills me more than even Roy’s version. Just listen. Especially when Lang’s vocals really get going.

 

FOURTEEN: “Monoply” by Shawn Colvin. I love every single song on her “Fat City”album and this one is devastating. Every single second of it. Sheer perfection.

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