He wrote the book in between, I think, 1990-93, and I sort of wonder if the world hasn’t moved on enough from then to where IJ would seem quaint to younger readers these days. I recall having very mixed feelings about the footnote/index gimmick–flipping back and forth between the front and the back did grow a bit tedious. Since you commented on “absurd extreme in their first world problems” that might put you off reading IJ, which was frequently about commenting on 1990s psychological problems and neuroticisms people were having. It’s hard to think what it would have been like in a post 9/11 world at all let alone Trumparama.

I still thought it was a really good book, though, some of his set pieces are absolutely ingenious like that live-action game of Calvinball that happens a ways through it, or the infinite Subsidized Time bit which actually proved somewhat prescient.
Oh and it’s about 960 pages without the index, not 2000.

Less successful was his short story compilation Oblivion in which I think there was a preface where he openly admitted that he was deliberately making the stories in the book impossible to read or follow because he liked it when books just told him “fuck you” and challenged him. I still recall liking his story “Mister Squishy” though, but there was another one about a teacher flipping out and threatening to kill a class full of little kids that I thought was just fucking stupid and I can’t really remember why (and I won’t be re-reading Oblivion to find out.)

So whether you like him or hate him, the “he badly needed an editor” thing is going to stay. On the basis of your criticism of him being a nerdy white overeducated spectrumite…yeah, I guess skip IJ.

One of the characters in Jeffrey Eugenides’ book The Marriage Plot is based off of DFW, bandana and all (the other male lead is based off Eugenides himself). I think you should skip that book though.