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I know some songs but don't have any records. Any guidance would be very welcome!
it's his best and it will utterly hook you into his world I'd reckon
I was a big fan of Smog but I didn't enjoy the final Smog album (A River ain't too much) and haven't re-engaged with his 'Bill Callahan' albums so my knowledge is really on the Smog stuff.
First few albums are very very lo-fi and although I personally like them I think it was with 'Wild Love' where I'd say he really found his voice and sound. So for me Wild Love, The Doctor Came at Dawn, Red Apple Falls, Knock Knock, Dongs of Sevotion, Rain on Lens and Supper are all essential. I really do love all those albums.
If I had to pick one I'd go for 'Knock Knock' as both just a great album and a good introduction - possibly his most 'accessible' record? The 'Kicking a Couple Around' e.p. is also a personal favourite.
Cat Powers version of Bathysphere also worth a special mention.
cuz it's the best: https://www.youtube.com/watch?v=yYg6eIH7qR8
or Wild Love.
Of the more recent albums, I'd say Sometimes I Wish We Were an Eagle is a good one to try.
Red Apple Falls, Knock Knock, Dongs of Sevotion probably the pinnacle.
It's a short, snappy album with some great songs (well, they are if you like his stuff) and the production is nice and warm.
Probably go on from there. I don't really feel there is any difference between his stuff and Smog's but I'm not much of a connoisseur.
Knock Knock (mentioned above) is also a great album (Smog).
the first half is just glorious.
For me A River Ain't Too Much to Love is his masterpiece. Haven't really been too fussed by any of the albums he's released as Bill rather than Smog.