@“MoH”#p113295 DFW was my favourite author for a good number of years. The way he described thought-spirals and intensive self-criticism felt like he was looking directly into my mind and describing what was in there. It's an amazing skill, but at the same time, I do find it harder and harder to relate to his works as time goes on.
I think success/fame at an early age was really bad for him. Having that amount of scrutiny and attention seems to have reinforced and strengthened his own self-reflective tendencies. Part of the way I have got over my feeling that everyone is constantly judging/hating me was understanding that most people just don't think about me the way I think about myself -- they are a lot less harsh, for one, and for two, they are a lot less _interested_. People just don't care about what I am doing as much as I do, which is in fact a very good thing! But when I imagine being in the situation where people were actually attentive to my works and my words, and I was on TV and etc, it would be easy to externalize these sort of thought-spirals and make them feel intensely _real_, because in a sense they are.
I think one of my major criticisms of his work is that I think he is missing an entire "register" of human emotion. His unwillingness to be "sentimental" means that the only emotions he's willing to seriously address are despair, loneliness, dread, etc. It's kind of weird to think that in a book as large and varied as _Infinite Jest_, there is almost no joy. Sure, there are jokes and levity, but they mostly come from farcical moments in which we, the audience/narrator, are able to laugh at the characters. I can't help but think of someone like Tolstoy, who is able to write stories that incorporate joy, humour, hate, anger, fear, romantic and familial love, death, etc etc, without any of these emotions feeling like they dilute or counteract the others.
There's a sense in which _Infinite Jest_ equates happiness and addiction, and is intensely critical of all sources of happiness. For all its jokes, there is this incredibly somber underlying foundation, and I don't think it is an explicit philosophical intention of DFW's as much as an aversion to actually tackling these emotions because they're the fodder of TV and "sentimental novels" and therefore not serious. I think this is a result of being hyper-aware of criticism and trying to pre-empt it in the same way the character in that story does.
And it ends up in the same sort of fashion, where all he can do is pre-empt and pre-empt and dance around and around, getting caught up in paradoxes and etc but never actually dealing with the criticism itself, never actually opening up those more basic and "primitive" emotions that are so strong they can't be danced around. That story is so deeply uncomfortable because it so accurately describes the way he seems in interviews, where he constantly says something that he obviously understands is insightful, and then stops and says, "Did that make any sense?" and at first you say, "oh, he's insecure and uncomfortable on TV" and then you read that story and you think, "Oh, he doesn't want us to know that he thinks he just said something smart," which is way more unsettling and a lot less cute.
... I think this whole post is a bit more harsh than I intended, because I _am_ sympathetic to what he went through and what he was writing about, and I do still think _Infinite Jest_ and a whole bunch of his stuff is absolutely great. Perhaps a lot of my current feelings are a sort of recoil from holding him in such high esteem for so many truly miserable years of my life, and now trying to move on. Unsure. Just had to share my thoughts.