
A collection of stories from David Foster Wallace is occasion to celebrate. These stories -- which have been prominently serialized in Harper's, Esquire, the Paris Review, and elsewhere -- explore intensely immediate states of mind, with the attention to voice and the extraordinary creative daring that have won Wallace his reputation as one of the most talented fiction writer of his generation.Among the stories are "The Depressed Person", a dazzling portrayal of a woman's mental state; "Adult World", which reveals a woman's agonized consideration of her confusing sexual relationship with her husband; and "Brief Interviews with Hideous Men", a dark, hilarious series of portraits of men whose fear of women renders them grotesque.
I'd say there's a lot of groundwork laid in the first 60 - 100 pages or so. After that, I honestly don't think it would be harmful to cherry pick interesting passages from the book. You could research interesting sections of the novel and target those for a first pass read through, then maybe later read it sequentially. There aren't really plot spoilers as the book is somewhat plotless.
Even still, I'd recommend the first read through be sequential. My first read through was, but I also skipped around a little bit. My favourite thing about DFW is his writing style. Also might help to whet your appetite for his voice by reading something like "A Supposedly Fun Thing I'll Never Do Again", which is a hilarious anecdote and commentary about his trip aboard a cruise liner.
In general, I'd say the best advice is to free yourself from the burden of 'understanding' the novel on your first read through and just enjoy the chaos. Besides, there is so much ambiguity in the novel that, even if you do crystallize some understanding, there's likely many alternative interpretations. That's where the re-reads get really fun.
He’s also written some really thoughtful literary criticism if you like that sort of thing (“Fictional futures and the conspicuously young” is a good example).
A supposedly fun thing I'll never do again (originally titled 'Shipping out') David Foster Wallace goes on a luxury cruise. There's a PDF version online, but the reading experience doesn't compare to reading it in a book. My copy is tatty by now, still keep going back.
If you like David Foster Wallace his other two novels "Broom of the system" and "The Pale King" are also great. The Pale King was left unfinished when he died and was completed (from various drafts and notes) as a labour of love and respect from his notes by his editor. It's genuinely extraordinary and could possibly even have been his greatest work if he had been able to fully complete it. As is there are certain minor things in it that I'm sure he would have revised (eg I noticed some sentences are repeated etc).
If you're not sure about David Foster Wallace I can really recommend his essays and literary criticism as consistently insightful and extraordinary and also his journalism. From his essays for a starting point I would recommend "De Unibus Pluram" and also "Fictional futures and the conspicuously young", and also "Roger Federer as Religious Experience"[1]. Of his journalism I would strongly recommend "Getting away from already being pretty much away from it all" which is an amazing write up of the experience of visiting a rural state fair and "A supposedly fun thing I'll never do again" which is the same sort of thing about going on a cruise ship. Both are very funny and perceptive.
If you like those you know what you're getting into with this novels.
[1] Especially if you like tennis. He also wrote an amazing essay about a tennis player who is very good but not quite good enough to make the top level and is struggling to break through. THat one is amazing but the title escapes me.
Okay, so this. Read it if you haven't. Probably the best essay on a generally "unheavy" topic I've ever read, and so iconic that "Cruise Essay" is dang near becoming its own genre, e.g. Gary Shteyngart's "A Meatball At Sea."