Haha—this is the first thing I've heard about GEB in years that makes me again somewhat interested in reading it. There was a point when I was a teenager where it seemed like probably the most interesting book on the planet, and I'd read a decent bit of it then; but years later—after studying a bunch of math, CS, and philosophy stuff—when I'd consider reading it there just didn't appear to be enough new meaty stuff of interest (though it still looks like an enjoyable packaging of many already familiar things). I also disagree fundamentally with the possibility of a material 'strange loop' resulting in another ontological category, so I feel like I'd be missing drive to reach the conclusion.

I'd be curious to hear any opinions on GEB by those with decently strong math, cs, and/or philosophy backgrounds—might it still be worth reading? (I mean it's damn long...)

If you are interested in the context analysis in Crime and Punishment then you can read just those few pages. He goes over just the first couple sentences of the book if I recall correctly. It's not an explanation of the context for the entire book by any means but an example of how much context could be needed to read a simple sentence.

His essay about machine translation is quite illustrative of the issues of cultural context as well. Even the best translations lose a substantial chunk of meaning, because it’s often not just what the author said, but also how he said it, which particular words were used, and subtle other meanings and gradations attached to that particular choice of words (and, in Russian, the word order as well).

When I was growing up I read a ton of sci-fi. One of my favorite works is “Stranger in a strange land” by Robert Heinlein. I had two different translations of it. One was good, another one was a turd, and neither came anywhere close to living in the US for 15 years and _then_ re-reading the book in its original form. And that’s sci-fi, a relatively “shallow” literary genre.

Indeed, while a separate issue from cultural context of 19th century Russian literature, translation is a literary genre by itself. I also noticed that Americans are generally unaware of this. Not that I'd blame them. I wouldn't care about translation myself if I had been a native English speaker and enjoyed immediate access to the enourmous body of English literature :)

ah shit. i also read C&P last year and GEB is on my shelf untouched. welp now i’m obligated...