Favorite musical outsider artists (whose work I truly, un-ironically enjoy) include David Liebe Hart (his stuff for Tim and Eric is obviously played for laughs due to his naivete, but his Christian spirituals are weirdly affecting), Florence Foster Jenkins (very odd opera singer), Lucia Pamela (weirdest pop singer ever - insists to this day that her only album was genuinely recorded on the moon), Jane and Barton (very minimal ambient-ish pop music; think a super sparse Grouper), Sensational (completely indescribable hip hop wackiness), and Shooby Taylor (the "Human Horn," whose scat singing has very odd punctuation and usage - bonus is that all his recordings are free through his website).
Isn't the ultimate example something like The Shaggs? In which one truly touches the limit of technical 'ability' (and even of pretty much everything else that's concerned with musicality even).
Apparently Michael Yonkers is considered a "Outsider" musician. Not 100% sure about that personally though. Maybe back then in the late 60's/early 70's, yes, It was strange for the time. but now? no so much.
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