Would recommend Sometimes I Wish We Were an Eagle (Bill Callahan, 2009), A River Ain’t Too Much to Love (Smog, 2005) and Knock Knock (Smog, 1999) as starting points
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And if you’ve seen High Fidelity then you’ll know
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Would add Dongs of Sevotion to this, myself.
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Considered including it but didn’t want to go overboard!
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Maybe the best album to ever come out on Drag City.
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Am listening again now 
still gives me goosebumps
Although Drag City is probably still my favourite record label and probably the Label that I have most records from….
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Supper is the best “boring” Bill Callahan album
It’s not his best overall but I reckon Vessel in Vain, Truth Serum, Our Anniversary is as good a three-song run as you’ll find in his whole catalogue
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It’s good but I think 2011’s Apocalypse is the pinnacle of his stuff for me.
Yeah not my favourite but Our Anniversary is lovely