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Overall, I say start at the beginning. Since you say you like his folk stuff and "some of his electrical stuff" you'd be getting the straight one man folk stuff to begin with. Then you can ease into the electric group stuff just as it happened. Ready for the House is a fine place to start, as it's where he did.
I totally disagree with jonathan's statement "The mystery surrounding the man is far more interesting than his music." I've seen Jandek live and he put on an amazing two hour set of pure unadulterated charisma. I love his records too, and while they may nto be the perfect music for every mood or every day, they capture raw emotion in it's purest form the way only great art can. The mystery is kind of cool, and has made for great album covers and an original aesthetic, but I get kind of annoyed by all the theorizing behind who he might be. Like Calvin says in the movie, refusing to participate in the mainstream media circus does not make you a recluse or a social misfit. Who he is has always been right there on the records to the extent that it was needed.
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