Here's a depressing tidbit of information: The "hacktivist," Aaron Swartz, before he committed suicide due to the hounding of the U.S. government, wrote a blog post called "What Happens At The End Of Infinite Jest?" This is sad more for the facts surrounding Swartz's end than anything else, honestly. Considering Wallace's suicide, and the large role suicide plays in the book, that it found an engaged reader who met the same end; but who maybe didn't struggle with crippling clinical depression, (and so maybe could have endured for longer) but instead, a sense of the law that values intellectual property moreso than actual human lives, makes the tragedy of Swartz's end felt all the more. Or even just: Dude was a person with interests, a container of multitudes the way we all are, and shouldn't be reduced to the bare facts of his life that can be chosen as "the most important" for the sake of some narrative.
The funny thing about the information that such a blog post exists, by the way, is that reading Swartz's evaluation after finishing the book, I thought, Wow, I didn't get any of that. That's not to say the book is bad, or it doesn't work. The things that actually occupy the scope of the book, that are delineated at length within its pages, and aren't just things you're meant to extrapolate or fill in the blanks with, are pretty rewarding. Honestly, the things that fall outside of the printed page, in the parts of the book that are meant to be in the reader's head, seem to stem directly from the parts of the book I felt didn't work as well as the others. Which is to say, the "wacky," "science-fiction" elements, which can also be characterized as "the stuff most directly inspired by Thomas Pynchon."
The difference between Pynchon and Wallace, to be reductive, is that Pynchon loves weed. This is one of the few biographical details I know about the dude, actually, and his books are, for all their darkness, constantly riffing, being wacky. A tweet I like, written by one @Dinkmagic: "people say Pynchon should win a nobel prize but 1/3 of everything he's ever written is about the weirdest pizza toppings he can think of" is funny in basic principle, and looking at Inherent Vice again, I realize that actually is a subject of discussion in the book, and not just something that WOULD be in a Pynchon book, on account of how high that dude gets on the regular. Infinite Jest is pretty adamantly anti-drug, anti-substance-abuse, pro-AA. The climax of the book finds the reader rooting for an addict, suffering through horrible pain, to not go on the painkillers that would cause him to relapse. Still the book makes clear that Wallace has consumed his share of substances and that the thing he finds to most mark the experience of ingesting marijuana is a constant paralyzing and recursive self-consciousness. That self-consciousness, and the way cycles of thought perpetuate themselves, is sort of the major motif, or power of Wallace's work, its ability to capture the nuances of thought that thoroughly.
It is not a pot comedy, in other words, which Inherent Vice basically is. The sort of stoner Pynchon is explains his lax and digressive approach to plotting and his sense of humor. The books Pynchon has publicly expressed his enthusiasm for are generally pretty loose and dreamy, occasionally out-and-out comedies. I haven't read very many of them. I did a Google a few months back and found a website listing all the books he's blurbed and was surprised by how few of them I'd heard of, and how many of them seemed slight. Maybe they are mostly books he found funny. The other thing I know about Pynchon is that he likes The Simpsons. He blurbed Donald Antrim's The Verificationist, that book is pretty funny, and great. He blurbed Steve Erickson's Days Between Stations, and that book has a fun dream-logic to it. The things that I took away from Infinite Jest that I thought worked or were impressive are not necessarily things I think Pynchon would get particularly psyched on in a book, just on a basic level of what constitutes a personality. Which is to say that Wallace seems like a dutiful student, or someone who wants parental approval for intelligence, in a way where Pynchon -- who has approached family in his books, from Vineland on, from the perspective of an affectionate and protective father who loves the people he's surrounded himself with -- just might not care about.
Infinite Jest has all sorts of smart and insightful things to say about being a dutiful student, by the way, and wanting parental approval, and fathers and sons. That stuff's great. The things about the character of Marlo brought be close to tears. I'm sure there are jokes in the book I laughed at. But most of the more outright comedic elements, the Canadian wheelchair assassins in drag -- are pretty tedious. The whole plot about Canada, subsidized time -- The whole idea of "The Year Of The Depend Adult Undergarment" is probably what made me not want to read the book for the longest time.
I am pretty sure I have read an interview with Wallace where he openly wishes that Pynchon had weighed in on Infinite Jest, by the way. It might be a Michael Silverblatt interview. This also feels sad to me, but maybe inevitable, and certainly not that sad in the grand scheme of Wallace's overall tragedy, of anti-depressants that stopped working, and being overtaken by clinical depression- That depression being described in the same terms of unstoppable inevitable which is both how he approached all of thought, whereas Pynchon's yarn-spinning has kept him alive and healthy for what is, at this point, an impressive length of time.
The other thing about Infinite Jest is I don't think anyone ever talks about it in terms of what the book is about, which is drug addiction and treatment. The notion of AA as a set of meetings where people are just talking then gives way to Wallace's belief in the ability of language to communicate as a way that can alleviate suffering. This stuff is great. (Although, viewing the convergence between these elements, and the father-son stuff, in a way that happens outside the book's parameters, as outlined by Swartz, makes the father-son stuff way sadder, in a tragic and somewhat mean way, that I'm not sure I think I enjoy. In that it's about the ghost of a father who committed suicide deliberately ruining his son's life so he can play tennis with him in the afterlife. But whatever, that's only implied in the text, not explicit, so even if it is intended, can be somewhat overlooked.) Reading it, I often thought, "Huh, I wish I could give this book to my dad, the guy who apparently enjoyed court-mandated AA meetings he went to but then stopped going when he didn't have to and said to me that he goes to bars at least partly because there's nowhere else for him to go, since people his age have families... Too bad it is so incredibly long he would probably never read it." I think people maybe read it now because of some sort of admiration for the idea of a suicidal artist, which is sad and off-putting. For years people read it because it was "smart," GENIUS even -- the fact that it is so long is evidence of its incredible genius! -- the cult of the male author that is particularly attracted to long books because they seem like a challenge, the pursuit of literature as a dick-measuring contest. (Which, for the record, Marguerite Young's Miss Macintosh, My Darling is an incredibly long book written by a woman, and I don't think anyone ever reads that book or talks about it.) The Dave Eggers introduction to the edition I have, written before the suicide, is really fucking shitty in this regard.
You should never read a long book just because it's long. Doing that will mean you don't read very many books, and that the books you do read will all sort of have the same system of what they value. Also, while I don't think you should read a book specifically because the author killed themselves and you just find that fascinating, if you do belong to such a death-cult, David Foster Wallace's short-story collection Oblivion has some shit in it that might blow you away, and I think that book is generally fairly overlooked anyway. If you want to read a good long book for a specific reason -- say, for example, that you are a goal-oriented person, who needs something to occupy their time and energy for a good long while, perhaps as a way of occupying your attention so you don't return to old ways of thinking and relapse to old behaviors -- Infinite Jest is pretty damn good long book.