More sad songs to break your heart
As previously stated, I am a lover of misery. Sweet, sweet misery.
For me, a sad song has to hit all the right notes (heh). So a poppy song about a traumatic breakup? Doesn’t do it for me. But put that shit in a minor key, maybe with some broken chord piano in the background, throw in some despondent lyrics about a lost love, then top it all off with some random emotional connection I have to the song? Misery central. Love it. LOVE IT.
I’m particular to songs of unrequited love, maybe because for me, it’s one of the most emotionally desperate states to be in. You’re not only sad because the person doesn’t love you, but it’s made worse by the fact that there’s nothing you can do about it. And even though our brains know this, there’s always this disconnect that pushes you to think, “But maybe…” and that just makes you more miserable. Our brains are cruel. Obviously this theme shows up in popular music in mostly romantic relationships, but songs about unreciprocated parent/child relationships also strike me particularly hard. Why doesn’t your dad love you? I don’t know, music person. I just don’t know.
Brandi Carlile, “Hiding My Heart”
And I wish I could lay down beside you
When the day is done
And wake up to your face against the morning sun
But like everything I’ve ever known
You’ll disappear one day
So I’ll spend my whole life hiding my heart away
This song is amazingly simple, both lyrically and musically, yet so striking and sad. A+ sad song. A+ song in general.
Beck, “Everybody’s Gotta Learn Sometime”
Change your heart, look around you
Change your heart, it will astound you
This is a cover of a a 1980 song by The Korgis, but Beck’s is more melancholy, in my opinion. The lyrics itself are actually not that sad, but the combination of the refrain “Everybody’s gotta learn sometime” over and over again resonates as a sad, true relationship lesson. It also helps that the song was also featured prominently in Eternal Sunshine of the Spotless Mind, a film about literally erasing a bad relationship from your mind.
David Bowie, “Everyone Says “Hi””
Everyone says
Don’t stay in a sad place
Where they don’t care how you are
Everyone says, “Hi”
On the surface, this is just a little song about a friend checking in with another friend. On the next level, though, there is the very real feeling that whomever is saying “hi” really, really, really wants the person to come home. 😦
Full disclosure: I am wearing a David Bowie shirt right now so I may be slightly biased to David Bowie songs. Still a damn good song.
Sia, “Breathe Me”
Be my friend, hold me
Wrap me up, unfold me
I am small, and needy
Warm me up and breathe me
This song has been done to death and it’s also not a song about unrequited love (or maybe it is. What do I know?). But it was used for the finale of Six Feet Under and it’s just the combo of the music and the awesome show and the driving montage and life events and death and ugghhhhhh. If you can watch this and not tear up you are a ROBOT.
Teddy Thompson, “Days in the Park”
And the postcards that you send
Excuses for the letters that you can’t write
And don’t you think I care
When you don’t come home at night
This one KILLS me. Teddy Thompson’s very famous father, Richard Thompson, was apparently a pretty lousy dad. This is his song about it.
The Velvet Underground, “Pale Blue Eyes”
It was good what we did yesterday
And I’d do it once again
The fact that you are married
Only proves that you’re my best friend
This is the one for me. This is the one that I hear and think, “This is why there’s music.” It’s so perfect in every way, but only in ways I can’t explain to other people to make them understand because it couldn’t possibly mean then same to them as it does to me. Everyone should have a song like this.
Smack Madness 
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