Ween puts out some really strange material. They are one of my favorite bands.
Beck had some strange music on Stereopatheticsoulmanure and Mellow Gold.
Aphex Twin (Richard D James) is way out there. It's so far out that it's had to understand and often hard to imagine that what you hear is actually music.
Foetus had some weird stuff in the 90's.
Michael Patton puts out some very interesting music.
For strange Hip-Hop, I'd look at the Anticon catalog and Definitive Jux. Lots of great stuff in there, but often very strange.
It would be hard to choose which is the "strangest", but if I had to, I would probably pick something by Aphex Twin.
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