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An Annotated Depressing Valentine’s Day Playlist

As a contrast to all the shallow and commercial tokens of love which suffocate us all during this Valentine’s Day season, I thought it might be nice to assemble a playlist of depressing songs I’ve listened to in dark periods of heartbreak.  Below are some thoughts on each song, here’s a link to the whole Spotify playlist:

 Say Anything – “Into the Night”

“A film if playing in my head / of you fornicating in his bed / the satin sheets are ruby red / like your nails that scarred my back”

 This song is pretty gnarly.  I listened to it a lot after I got dumped by this girl who had been cheating on me pretty consistently.  I had suspected as much; at one point I even saw an email she sent to this guy where they talked about how they had been sleeping together behind my back.  But I was “in love” (naïve), so I bought her horseshit.  Young Love!

Brand New – “The Boy Who Blocked His Own Shot”

“It’s cold as tomb, and it’s dark in your room / When I sneak to your bed to pour salt in your wounds” is a website that tracks & logs all the music I listen to on iTunes & Spotify.  The couple times I’ve been dumped or gone through emotional turbulence, my listen-count for Brand New’s Deja Entendu album suddenly spikes.

 Adele ft Childish Gambino – “Rolling in the Deep (Remix)”

“You think that I been fucking other girls, you know I’m not/ Come back to me like hipsters to Blogspot”

This Adele song is already a pretty devastating breakup ode, what with “the scars of your love, they leave me breathless, I can’t help feeling, we could have had it all,” (preach, girl), but the Gambino lyrics take it over the top. The weekend after a girlfriend left me, I had to fly to Maine for a wedding (turns out everyone is right; a wedding is the last place you want to be after you get dumped).  I listened to this song on repeat for the whole plane ride from State College to Maine and back.

Childish Gambino – “So Fly”

“And I don’t really understand the thing we had / I wanna try again, but it would just be sad / You are the only one  / who’s ever let me be me”

This song is beautiful and if you can’t relate to the sentiment of these lyrics, then fuck you and your story book Valentine’s Day.  Come talk to me next year after he broke your heart and you cried for a month.

Sigur Ros – “(Untitled 1)”

Icelandic band Sigur Ros have an album which is either untitled or called ( ), depending on who you ask.  All the songs are untitled and are in a made-up language the band invented called “Hopelandic,” which kind of sounds like Icelandic but is just nonsense…  the CD came with blank liner notes with the idea that the listener could fill in what the songs meant to them.  I never did that, but if I did, I would have written about how hard it is to maintain relationship whose foundation is sparse text message flirting with a girl from home when you’re 17 and away in New Hampshire working as a counselor at a boy’s camp.

Bon Iver – “The Wolves (Act I & II)”

“Can’t you find a clue / when your eyes are all painted Sinatra blue”

Justin Vernon (the guy from Bon Iver) wrote the album For Emma, Forever Ago alone in a cabin in the woods of Wisconsin after he got dumped.  I listened to it a lot after I broke up with my first long-term girlfriend because I thought that’s what I was supposed to do.  I now realize I was being melodramatic and we actually didn’t have anything in common.

Brand New –  “Degausser”

“I can’t shake this little feeling / I’ll never get anything right”

Brand New has a special place in my heart as they were my favorite band all through high school.  In high school, I never had the courage to tell any of the girls I was in love with that I was in love with them, so I would just listen to songs like this one and be bummed out about it.

 Kanye West – “Runaway”

“If you have someone tonight/ hold them tight, tight, tight”

The above lyrics aren’t in the studio version of the song, but when I saw Kanye live last semester he did this weird thing at the end of “Runaway” where he just repeated the above phrase like 30 times.  It bummed me out because I didn’t have anyone to hold tight tight tight.


Here’s a link to the whole Onward State Depressing Valentine’s Day Playlist, there’s even more tracks on there.  Alternatively, if you’re looking to celebrate your Valentine’s Day in a more traditional (or marketable) manner, here’s a link the Onward State Valentine’s Make-Out Playlist.

Dennis McNamara (@dennismcnamara) is a senior studying International Relations.  This Valentine’s Day, he can be found crying alone in the back row of the State Theater’s presentation of Casablanca.


About the Author

Dennis McNamara

Dennis McNamara is a senior studying International Relations. The product of a long and muddy Irish lineage, Dennis blames that sour heritage and his Boston area upbringing for the flaws in his character. The only paid writer for Onward State, Dennis has never been described as a team player as he often thinks of himself as “the smartest guy in the room.” In addition to contributing to Onward State, Dennis is also Creative Director for Full Ammo Improv. Dennis isn’t sure when he’s kidding either.



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