Pynchon’s Against the Day is the grand-daddy of this genre - I’ve read most of the books mentioned already and I’d put Against the Day way, way out there in a league of its own. Doesn’t mean it’s good, mind, just unique. Literally unique, as there can’t be more than 5 people on planet earth who could write a novel like this, and of the five of them, only Thomas Pynchon has the literary reputation to get it published.
Only drawback is that the prose can be hard work, on a sentence by sentence level. Pynchon is a real prose stylist and the going can be tough at times.
Many of the multi-page (!) footnotes (endnotes?) in Wallace’s Infinite Jest do indeed have their own footnotes. I’m in the middle of re-reading this now, and to me it seems to be exactly what the OP is asking about, and the extraordinary details of his fictionalized world above and beyond the plot items are what I love about it.
This does not mesh quite as neatly into your description of others, but for timeless humor full of rich descriptions, go for P.G. Wodehouse’s books on Jeeves and Wooster. I’ve only read The Code of the Woosters so far, but it was even more delightful than I expected based on the BBC mini-series, and that’s saying something. Wodehouse has a wonderful way with words.
I’ll third or fourth Infinite Jest. It sounds tailor-made for what you’re asking – there is even a slight undercurrent of science-fictiony elements. I recall a long digression on the cultural trappings of the videophone that was hilarious.
I’ll also vote for Cloud Atlas. Pretty fascinating Russian doll of a book.
You can also look into Flann O’Brien’s The Third Policeman. Borges on a drunken bicycle tour of rural Ireland, with numerous footnotes tracing the remarkable career of De Selby, a polymath/idiot scientist who among other things considers darkness to be “black air.”
God, yes, or Nooooooooo. Half way through it, I was close to become an axe murderer. wunderkammer, treat these volumes like the Overlook Hotel … and you’ll be fine (no, don’t burn them, flee from them).
But what about Tolstoy’s War and Peace? It’s long, very long, hell, the complete list of characters goes on for pages and when you think you are through with the novel, the epilogue starts and goes on and on … and is followed by a second one.
Still, it’s a classic. And quite entertaining.
Speaking of classics, if you like the fantastic, The Arabian Nights: Tales from a Thousand and One Nights, are not just great stories, you will also discover time and again a) how often modern authors … borrowed … from this source and b) how much more fun the stories are compared to any Disneyesque retelling.
The science fiction novels of Jack Vance would be exactly what you’re looking for. He has a style that’s pretty much unique in science fiction as far as I can tell. It’s not at all focused on futuristic technology, though that stuff exists in his universe, but rather on the social scene. Often times he dashes of half a dozen different planets in a single novel, each complete with its own diet, clothing, architecture, social norms, and government. It’s indescribably brilliant. Araminta Station is a good place to start, especially if you like long books.
If it’s length you want then you should go for Anthony Powell’s A Dance to the Music of Time which comes in 12 volumes and about 3000 pages. There are hundreds of characters including one hilariously grotesque one called Widmerpool who features throughout.
High Fantasy, the Realpolitik fantasy novel about a nasty succession war that goes for years.
The Urth of the New Sun series by Gene Wolfe
About a young boy from the torturer’s guild and his strange rise to power on Earth after the Sun has started to die.
Shantaram by Gregory David Roberts
A great novel about an Aussie expatriate running from the law and hiding in Bombay, about his travels working for the Afghani Mob. it really touches on the exotic in Bombay. A film is in the works directed by Mira Nair and starring Johnny Depp.
LOVE this thread! So many of my favorite books have already been mentioned. One which hasn’t, and which fits the criteria very well I think, is The Sot-Weed Factor by John Barth. Long, convoluted, hilarious, brilliant historical fiction.
The Effect of Living Backwards by Heidi Julavits. A plane gets hijacked, but instead of physically threatening the passengers, the captors decide to play psychological games with the passengers. Every other chapter in the book is a story from one of the characters’ childhood, providing insight into the reasons they behave the way they do.
Well, I came in to mention *House of Leaves *and Foucault’s Pendulum, but both have already been cited. So, I’ll offer *Gravity’s Rainbow *by Pynchon, the virtual definition of long and cluttered.