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Comments
I would start with the West Of Rome and Is The Actor Happy? LPs and see what you make of them both. WOR is pretty downbeat and lo-fi, but features a sack-load of his best, blackest, bleakest, funniest songs...it also contains my all-time favourite song of his, Lucinda Williams, which chokes me up every time. ITAH is a lot more polished, with a bigger band, and fuller arrangements...again, a lot of really great songs, highpoint being him and Michael Stipe harmonising on Guilty By Association. There are standout tracks on all his records beyond those two, but I'd single out the Drunk LP in particular for the track Supernatural.
There's a feature-length documentary about him on youtube (the name escapes me) which is well worth watching. A huge talent, and even now, a terrible loss.
I'll try and watch the documentary later...