One way I had thought of describing Infinite Jest is as a long scream with funny bits. It’s an evisceration of Amarican-style, commercial, pleasure-based culture where there is so much choice that choice is meaningless, in a USA where people are over-entertained and sad and bored and lonely. Especially lonely.
I set out to read IJ as a challenge to myself. I read some reviews and comments on it and every one said it was difficult. It's certainly long, at over 1000 pages if you include the 388 footnotes (yes, it is a novel) that are invariably referred to by reviewers.
There's a LOT of detail, whether it's the description of a room, or a person, or the person's state of being, or the drugs they use, or the tennis academy that is one of the locations of the story, or the workings of AA or whatever. The plot is not-quite-hidden in the details, and I'm not sure I could say exactly what the main plot is.
Infinite Jest was first published in 1996 and its setting is the 2000s, so there's an element of futurist technology. One device key to the story is something like what we know as a DVD, and there is a particular one of these around that has such a high entertainment quotient (not DFW's word) that once a person starts watching it they cannot stop. One plot line is to do with various agencies seeking to find and destroy the master copy of this Entertainment, which of course can't be watched by anyone wanting to destroy it. Such pleasure is fatal! Which creates funny and gruesome and fascinating scenarios.
Protagonist Hal Incandenza is a teenage tennis star at an invented academy. The training regime is horrendous. And, as with most of the contents of this book, it provides a context for exploring a whole range of ideas about society and power and success and so on. Including loneliness. The man who created The Entertainment was a film-maker (he's committed suicide before the book begins) and Hal's father. The mother of Hal and his two brothers is a really creepy character who is so nice and considerate and outright good, she gave me what DFW calls in a couple of places the "howling fantods."
Across the road from the tennis academy is the house for people getting off drugs. That's where another protagonist, Don Gately, is. A main source of treatment is going to AA meetings, and IJ includes an exhaustive level of detail about these meetings. "Yes, of course 'one day at a time' and such are clichés, but, hey, they work."
There are a myriad more characters, themes and story threads, such as the Concavity—a huge area encompassing Vermont and part of Quebec where no-one lives and the trash from the northeastern cities is catapulted to. The various plots and characters are carried along on an accretion of details.
The writing is extraordinary. I still haven't figured out why some sentences start with 'And but so...', or variations of that. It's not possible to ask, because DFW himself committed suicide in 2006. There are plenty of clips of him speaking on YouTube and masses of articles about him online, but I haven't found one that asks why he started sentences like that.
So much more could be said about Infinite Jest, and has been—try googling it. My conclusion is that in the end it is maybe a plea for doing our best to live in an actual, present world, and never mind an imagined (remembering is imagined) past or future. Or something. Anyway, I found it utterly worthwhile to make the effort and persist through what were almost boring bits, and excruciating descriptions of coming off drugs.