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Swans, anything Michael Gira has pretty much been involved with.
This, although I wouldn't call them underrated/obscure, as they're pretty big in their genre/scene.
I would also recommend:
- Paavoharju (Finnish band, could be called modern psych-folk, but it truly transcends any label I can come up with at the moment.)
- Machinefabriek (Dutch sound artist, known for his melancholic ambient/drone pieces.)
- Sun Ra (Not really unknown, but he's a great start if you want to get into free jazz.)
- Circle Takes the Square (Emotional hardcore oriented, probably greatly surpasses any "emo" act you know, pay attention to their lyricism and their way of changing mood and tempo in a matter of seconds.)
- Datach'i (Glitch/breakcore/IDM or whatever you want to call it, his work gets my vote for the most mind-numbling music their is available.)
- Grouper (Drone/shoegaze music; in my opinion, best to be described with the literary term "spleen".)
- Pink & Brown (Don't try this if you don't like noise rock, if you do, you even might need a few listens to get into it, it's pretty rewarding afterward.)
- Lightning Bolt (Noise rock of a more entry-level band to get into the genre.)
- Lydia Lunch (Next to Jarboe from Swans, probably the most important female front runner from the 70's post-punk scene.)
- Mùm (Icelandic post-rock from a different level then the more known Sigur Rós, look or the early recordings that include Kría Brekkan in the line-up.)
- Pocahaunted (Two girls making the folklore-like drone music, can't give a better description.)
- Zu (Avant-garde free jazz music, what more could you wish?)
I could go on for a while, bringing obscure music to light, is one of the few things I've stayed really passionate about over several years. Don't want to overdo it here though.