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Homestuck
I've written various descriptions of Homestuck over the past few years, in various places, for various people. The more I've written them, the closer they've converged to the description you see below.
I think I'm done repeatedly rewriting the description from scratch every time. I'm just going to put the entire thing here for future reference.
Homestuck is a Multimedia Internet Thingy by Andrew Hussie (mostly), that broke the bounds of being a webcomic almost immediately, and eventually became an anime.
What It Is
Okay, seriously, though. Homestuck is a work that takes full advantage of existing on the Internet. The prose and storytelling of Homestuck are presented in an unorthodox format that utterly defies description... and would still be a compelling story if stripped of the "gimmicks" (not that you could strip Homestuck of the gimmicks, they're integral to its identity). When averaged out across its entire run, Homestuck contains more text than the Bible (...ish; counting the exact amount of text in Homestuck is very difficult since a large amount of it is locked away in point-and-click adventure Flash pages and Homestuck is exceptionally good at visual storytelling) and updated more frequently than any other webcomic in existence. The music much of this story is set to does not understand genre, and is all the better for it.
Trying to describe what Homestuck is about is equally impossible. Is it a creation myth? A ludicrously complex time travel tale? A handful of teenagers whose internet friendships with people they have never met are treated as real and valuable? A story about the essence of identity? Science fiction with fascinating worldbuilding and aliens? An allegory for the increasingly all-consuming nature of digital reality? A meditation on the nature of free will? A dumb joke about Con Air extended until it has gone thoroughly dead, revived, and then milked dry again? All of this and more.
Homestuck has been called the first true example of a "hypercomic" - i.e. a hypothesized comic-related entity first theorized about in the earliest years of the Internet, whose previous examples were all Art rather than attempts to tell a story through the medium. (I prefer calling it a "multimedia internet thingy".) Homestuck has been compared to James Joyce's Ulysses. Andrew Hussie has denied that he ever wanted to create anything deeply groundbreaking or artistic, he just wanted to create what was in his mind. Honestly, I believe him.
Fandom
For several years, Homestuck had one of the most rabid fan communities out there, rivalling even the fans of mainstream works like Doctor Who in sheer energy, depth, and prolificness. Homestuck was partially written by its fans, with Hussie frequently taking fan suggestions and fan theories and tossing them into canon, increasing engagement and adding further depth to disparate elements that would have been one-off jokes in other works. Canonized fan speculation includes LGBT relationships, which were added to Homestuck years before mainstream acceptance, and are integrated well into the narrative. A notable Homestuck update (i.e. significant content dump) from 2011 broke Newgrounds, Megaupload, Livestream, and Tumblr, in that order. Even now, when something Homestuck-related is released, a thousand thousand people throw aside the trappings of normal life and become screaming fans again for a couple days.
Homestuck itself could be described as being a "cult classic", I suppose, but even now the influence of Homestuck still bleeds out into the greater cultural sphere. The fact that Homestuck was arguably partially written by its fans encouraged said fans to branch out into creating their own works, and many of them have since become extremely good and high-profile. Undertale is by Toby Fox, a Homestuck musician. (According to folk legend, Undertale was conceived of in Andrew Hussie's basement. I have been unable to either verify or disprove this.) The maker of those virally popular SCP horror games, Mark Hadley, was originally a Homestuck musician. Many of the people who work on Steven Universe are fans. Alexandra Douglass, previously a Homestuck artist, was employed drawing for the Sonic Mania webseries. A good portion of the soundtrack for Starbound was composed by Jeremy Iamurri (Solatrus), who was also a Homestuck musician. I can keep going.
Miscellany
A couple years after the ending, Homestuck (intellectual property, website, and all) was sold to Viz Media. After some initial consternation, most of the fandom has settled into some level of acceptance. For a long time, Homestuck being an anime was a common fan inside joke. The new involvement of Viz, which is an anime-property-related company, makes that some level of reality.
Sweet Bro and Hella Jeff is a "webcomic", ostensibly drawn by a character from Homestuck, that is a spoof of poorly-drawn amateur webcomics and a source of in-universe memes. It is filled with purposefully bad image editing that douses everything in JPEG artifacts, obnoxiously bright clashing colors, exaggeratedly poor anatomy, and gratuitous and uncontextualized NSFW material. This is where the "I told you about stairs" jokes are from. There was a recent Kickstarter for a Sweet Bro and Hella Jeff book, with all-new material not previously featured on the site, and KC Green and dril (yes, that dril) as co-writers.There is a Homestuck-based videogame, or videogame series, or expanded universe, called Hiveswap. Its Kickstarter raised something like 2 million dollars, which was the highest-grossing Kickstarter for a video game at the time (this was in an age before Double Fine Adventure, so it didn't have much competition at the time, but still). The studio originally contracted to actually produce the videogame may or may not have committed fraud with said Kickstarter money (details are unclear, and probably under NDA anyway), so it was delayed multiple times and is coming out episodically. Hiveswap is a point-and-click adventure game (mostly) that delves further into Homestuck's worldbuilding and contains much of its idiosyncratic writing style and charm.
The Hiveswap Friendsims are a series of bite-size 99-cent visual novels about making friends with many of the trolls that are supposed to later be featured in Hiveswap. (They are of dubious canonicity. You play as the blank-faced "MSPA Reader" and there are many mutually exclusive routes.) I think they are supposed to fund the production of later Hiveswap, but I'm not sure.
There is a persistent rumor that Andrew Hussie is the mind behind the erotic writer Chuck Tingle.
The musicians behind Homestuck have been undercredited. There are several albums with "outtake" music that never ended up in the comic proper. Probably the most notable of these albums are P[S] and Stuckhome Syndrome. Go listen. Maybe pay them money.
Conclusions
Some people say Homestuck peaked around the end of Act 5. Some people say Homestuck's ending was incredibly poor. Some people even refuse to acknowledge the canonicity of Homestuck's ending. I'm not sure I agree. Updates became ever less frequent after the end of Act 5, and there are arguments that the subsequent plot descended into incomprehensibility, but I do still think the writing and charm remained until the end. Andrew Hussie brought in increasingly many people to help produce Homestuck, first with music, then with art, and eventually with everything else. In the end, I think he gave its future to the fans. Which is fitting.
Do I recommend Homestuck for reading now? I don't know... sort of? Homestuck itself is so large that it would likely require a week-long bender to read in anything approaching its entirety. Its beginning is actively misleading as to the nature and depth of the narrative it eventually becomes. Starting anywhere other than the beginning is sometimes recommended, but results in losing a good fraction of the context provided by the beginning sections. Later on, the tone fluctuates wildly. Retcons, as in rearrangement of previous canon to better accommodate later story, are an actual plot element. Being associated with "Homestuck fandom" is not nearly as much of a stigma as it was for a while, but the fact that I have to bring this up is itself notable. Reading Homestuck is a fundamentally different experience after the fact compared to what it was at the time, because we are no longer in the heady days of reader suggestions and Homestuck-could-update-at-any-time culture. Even with all these disclaimers, though, Homestuck is a fascinating story, told in a unique medium and style that still only has a single-digit number of examples. It has had an outsize influence on much of fan-culture, the videogame world, and (to a lesser extent) culture in general.
I have been a Homestuck fan since 2009. I will likely remain a Homestuck fan for the rest of my life.