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Thank you, waterbutt - and it's an interesting question that you raised. Does it detract from the overall credibility of a musician when they write songs in the first person but from an outsider's perspective? After all, rappers get a lot of shit when they write lyrics about lifes that they have not personally lived.
But I think this case is different from that. Will Oldham doesn't step up to the mic and announce, "I am Will Oldham and I have had sex with my sister, muthafuckas". No, he simply writes songs in a literary, artful way like a novelist or an actor would approach their craft. I would say that any strength or weakness comes only from Oldham's imagination and talent. If you take his words seriously and then are disappointed that he is not an actual Appalachian mountain man, well, that's not his fault.

Speaking of actors, Will Oldham is one of those too. He was in a semi-famous recent indie flick called "Old Joy" and also a film called "Matewan" in 1987 - filmed when he was a teenager. He plays a young preacher and the setting is the true story of a coal miners' strike in the 1920s that turned violent.

I haven't watched it yet although I've been meaning to for oh so long. My point is Oldham can act and that definitely comes across in his songs (and especially in his live shows). He appears very authentic no matter what he does.

So, my next Oldham review is Viva Last Blues by Palace Music. This is an important album to me in a larger way than just in terms of the Squirrel Bait family. It is probably my favorite Oldham album and one of my all-time favorite albums as well. It was also the first Oldham album that I heard and I bought it randomly, never having heard of him. So that I don't have to take up my review space here is some personal backstory:

1995. I had a lot of free time and I was a regular at the local record store (Plan 9 in Richmond, VA). I had recently started buying vinyl because it was cheaper than CDs and I had a cool old record player and my dad's bigass 70s speakers. So I was looking through the 'new releases' section of records and came across Viva Last Blues.

I already liked the skinny leopard-man on the cover and the title so I turned it over and saw the Drag City logo and Steve Albini's name in the credits and immediately decided to buy it. I brought it home, put it on and fell in love with the first track even before Will's atonal, voice-cracking vocals started. Of course after they did I liked the album even more. Review coming soon.

*Note: There is a glaring omission in my There is No-One... review. I left out a crucial credit and that goes to Paul Greenlaw who played banjo on the album. The banjo is an essential element of the album so I'm sorry about that, Paul.