The Velvet Underground - Heroin
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The construction of this song is so utterly brilliant that I feel like I can understand on a deep level the feelings and undercurrents here even though I've never done drugs. Listening to this is a singular experience, and it's probably the greatest noise freakout-with-a-purpose I've heard.
The Mountain Goats - Jenny
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This song is freedom and joy. Period. This is gonna be hard cause I'm gonna be tempted to put Heroin and 7 Mountain Goats songs lol, since John Darnielle is so brilliant at songwriting, it's like listening to living short stories.
Talib Kweli - Where Do We Go
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quoting a Last.fm comment that couldn't sum it up better:
Such a beautifully sad song...
The Mountain Goats - Family Happiness
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I'll just do Mountain Goats every other one I guess.
quoting John Darnielle: "I think the reason that I had to wait 10 years or so to put that one into the stage set is to build up reserves of anger. When you write it maybe you have a moment, but you can't do that every other night or whatever. But just store a little bit of rage in a corner there somewhere inside, and then at some point you go 'oh guys it's time to do Family Happiness.'"
It's such a vividly realized scene set by amazing lyrics and the music just bristles with emotion, fear, uncertainty, love/hate, all of it.
CunninLyunguists - Mexico
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Another group that could do a whole list and have every one be a favorite song. This is the most grounded, realistic love song I've heard, and it's beautiful in that way, without being too sad. It's hopeful.
The Mountain Goats - Chanson Du Bon Chose
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Translated: Song of a Good Thing. The wondrous moments of reconnection with everything good and joyful. Brilliant story scene setting lyrics, it's like you can picture yourself right in that very situation.
Lupe Fiasco - Hurt Me Soul
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If you want to know what hip hop is about, just listen to this song. Insanely good lyricism, flow, meaning here. It's deep. Also I connect cause Nas's It Was Written was one of my very introductions to hip hop too.
I guess I'll go with
Nas - The Message
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as my last one to develop that. The first song that attached me to hip hop. So smooth, flawless. Nas is the greatest rapper ever I contend. The evolution of his career from street kid to legend and elder statesman of hip hop and the many turns in between is fascinating, and he's remained relevant throughout (even his crappy sellout phase in the late 90's ended up as a stepping stone for growth).
The other Mountain Goats songs I wanted to put on, check them out if you like the above:
Nine Black Poppies, Going to Georgia, Riches and Wonders, There Will Be No Divorce, Lovecraft in Brooklyn, Moon Over Goldsboro.