Playlist: The Saddest Songs I Know

From time to time, I'm going to list the best songs that capture a particular mood. In this first installment, enjoy a (pretentious) recap of the saddest songs in my collection. Feel free to nominate your own choices.

God Moving Over The Faces of Water – Moby: Built around a piano refrain that sounds like rain, this instrumental slowly becomes a thunderstorm of raw sorrow. When the world finally comes to an end, this will be the song God plays over the closing credits.

Where Did You Sleep Last Night – Nirvana: An obscure blues song about infidelity is remade into the quintessential Kurt Cobain record. I don’t think any other Nirvana performance better represents the power of Cobain’s pain ridden voice.

A Change Is Gonna Come – Sam Cooke: Written in response to Bob Dylan’s civil rights song Blowing In The Wind, Sam Cooke shows how even the saddest song can be empowering. The pain of centuries of oppression distilled beautifully into Cooke’s voice. I can’t imagine the world will ever hear a more moving performance.

I See A Darkness – Johnny Cash: Johnny Cash brings a certain gravitas to this Will Oldham cover. Its cathartic chorus could make even the toughest cowboy cry. A dark song about battling your demons and hoping that love will offer redemption.

Mad World – Michael Andrews & Gary Jules: Another end of the world type song. While lyrically awkward, this Tears For Fears cover creates a mood that is simultaneously ominous, gorgeous and terrifying.

Twilight – Elliott Smith: The saddest and prettiest song of Elliott’s brief career - his voice has never sounded lonelier. Off the otherwise unremarkable “From a Basement on the Hill.”

The Funeral – Band of Horses: If you’ve ever received the shock of suddenly losing a loved one you’ll understand the chorus’ haunting refrain. A song this great shouldn’t come so early in a band’s career – it just overshadows everything else.

Cold Wind – Arcade Fire: This is the song you play after the funeral, when you’re leaving town because all the memories have turned bad. In my version of Six Feet Under, this is what Claire Fisher would’ve been listening to in the car on her way to New York.

Nightswimming – R.E.M.: More of a song about nostalgia than say broken hearts, yet equally heart breaking. The lyrics are opaque and fragmented but it paints the perfect picture of innocence lost (whatever that phrase means).

Wish You Were Here – Pink Floyd: I’m not a big Pink Floyd fan, but if you don’t like this song, you have no soul.

Nothing Compares 2 U – Sinead O’Connor: Easily the most pop sounding song on this list, but after Sam Cooke’s A Change Is Gonna Come, also the most beautifully sung. This is the first song that ever made me cry.

Heart Cooks Brain – Modest Mouse: Modest Mouse is such a unique band - their sound is impossible to describe and the lyrics are at once smart-alecky and heartbreaking. It’s a unique sort of sadness, one that comes from feeling stupid about feeling sorry for yourself. It’s a shame Isaac Brock no longer writes songs like these.

On the Nature of Daylight - Max Richter: Another powerful instrumental that will make you want to crawl into the fetal position and rock back and forth. When World War III breaks out, this is what will be playing as the bombs drop in slow motion from the sky.