"Clear Spot" was the first one I bought, and it served pretty well as an introduction - both "Big Eyed Beans From Venus" and "Golden Birdies" show his avant-garde side, but the rest is pretty accessible. "Trout Mask Replica" is probably his most influential album, but perhaps not the best place to start as it showcases Beefheart at his most unrestrained. Buying that one first would probably be a bit like snorting heroin before you've sampled weed.
Apart from "Unconditionally Guaranteed" and "Bluejeans and Moonbeams", I don't think he's made a dodgy album, and even those two have enough great moments to make them worth sampling after you've tried the rest.
"Shiny Beast" is my personal favourite. V. eclectic, under-rated and mostly pretty accessible stuff.
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