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Music on Trial: the saddest songs, March 14

Alright guys, I’m leaving my identities of Chancho Watson and Hostradamus and putting them to the side for this personal piece on the Best Sad Songs Ever. Valentine’s Day is over, and that one dude or gal maybe isn’t as interesting as you thought they were, and it turns out that a night with them is like spending a night at Abu Ghraib. No worries – Horacio is here to ease the pain with this playlist.

Side story: When I was young, I watched “Toy Story” plenty of times. The song that always got to me was Randy Newman’s “I Will Go Sailing No More,” which appeared in the film after Buzz Lightyear finds out he can’t fly. It made me sad every time, and I’m pretty sure my brother would play the scene over and over as torture.

Some other songs of the downtrodden:

“Skinny Love” by Bon Iver

This dude apparently had a lot of pain when he wrote this. He had girl pain, band break-up pain, was suffering from mono – Justin was dealing with it all. This is the go-to song when that girl you like didn’t wave back at you. It may be because you got wack fashion sense, or because she doesn’t acknowledge your existence. It’s cool though because Justin Vernon gots you. SAD-METER: Basic Level Pain.

“Songs for Richard Collopy” by Sun Kil Moon

If Bon Iver is break-up music, Sun Kil Moon is divorce music or my-wife-passed-away music. I don’t even know who Richard Collopy is, but by the time you listen to the end of this song, you will find yourself crying at his eulogy with snot running down your heart-drenched face. SAD-METER: I don’t even know who you are, but I feel you dawg.

Literally any Bright Eyes song ever

No comments necessary.

“Hate Bein’ Sober” by Chief Keef

This song breaks from traditional, emotional, heartbreak sad and deals with the pathetically sad happenings in the hip-hop scene. Chief Keef provides a gripping account of how much he hates not being inebriated despite the troubles it gives him, including failing to spell the word sober. SAD-METER: I’m too sober to listen to this.

Any song by Sigur Ros

Though this Jonsi dude sounds like a majestic singing elk or the air of a helium balloon going out, he has songs that could put you to sleep and make you cry at the same time. SAD-METER: An elk is singing me to sleep.

“Jerusalem” and “Dopesmoker” by Sleep

These are absolutely tragic records by the stoner metal band Sleep. Sleep was given about 40,000 dollars to record a new record, and sources say that they spent it all on weed and recorded for just an hour while high. Sad on various levels. Or actually not that sad – kind of epic, depending on who you ask. SAD-METER: Empty.

“Started From the Bottom” by Drake

I’m still at the bottom, Drake. I’m still here. It’s cold too. Sidenote: Aleksander, turn up the heat please. SAD-METER: I’m broke. Send help please.

“Dead Flag Blues” by Godspeed You! Black Emperor

Picture this: The world is ready to end by a cr, the bag lunch line has five minutes left and they just ran out of multigrain PB & J’s. Vegetarians are the first to go includes me because the vegetable sandwiches are contaminated with venomous cucumbers. Furthermore, the epidemic somehow sucks in all the baseball caps in the world so athletes at St.Olaf refuse to come outside without one, and we’re only stuck with weaklings also includes me to help us out.


“All My Friends” by LCD Soundsystem

A song that describes so much of the college experience. It’s a song about letting go and holding on to the memories you’ve created. Somehow it encapsulates those failed weekends and the great ones you’ve had. It’s a beautifully sad-yet-joyous piece that tells us about our past and how much we’ll miss it. It’s about growing up and reflecting on what exactly just happened in your life and where it’s headed. SAD-METER: Holy cow. I’m graduating in two and a half months.

Signing off with some sadness,


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