Discworld series is my first thought. Lots of meta-humor, giant cast of recurring characters.
The Thursday Next series (Jasper Fforde) does a bunch of meta jokes too. posted by Garm at 9:02 PM on September 30, 2011 [2 favorites]
Definitely Discworld and the Hitchhiker's Guide to the Galaxy. I can't think of much set in modern culture that is that way though. Good Omens will trip your trigger.
There's one American author that I'm totally blanking on. One of his most popular books was kind of a parody on Jesus. Like about his best friend or something. Christopher... something... really blanking. posted by OnTheLastCastle at 9:19 PM on September 30, 2011
I think OnTheLastCastle is thinking of Lamb by Christopher Moore. posted by neushoorn at 9:22 PM on September 30, 2011 [3 favorites]
Middle to late Discworld novels were my first thought as well. They have a similar mix of meta-humor, parody, and warm and engaging characters. The City Watch and Witches sub-series have ensemble casts like Community. And given the D&D episode and Dan Harmon's role in creating Summoner Geeks, a fantasy series is not a stretch as a comparison. Here's a Discworld reading order guide.
And given the D&D episode and Dan Harmon's role in creating Summoner Geeks
I had absolutely no idea that Harmon was a Dead Alewife, and knowing that fact has just slid two disparate parts of the universe into perfect alignment. Thank you, Monsieur. posted by Strange Interlude at 9:36 PM on September 30, 2011
I immediately thought of Douglas Coupland -- Jpod! posted by Ostara at 9:39 PM on September 30, 2011
Douglas Coupland is solid. I was thinking of Christopher Moore, thank you. I have that on my list to read. posted by OnTheLastCastle at 9:44 PM on September 30, 2011
Mark Leyner & Chuck Klosterman posted by morganw at 10:06 PM on September 30, 2011
The Brief Wondrous Life of Oscar Wao, by Junot Díaz, resonated with me as an Abed fan. posted by AkzidenzGrotesk at 10:08 PM on September 30, 2011 [2 favorites]
It's a bit of a stretch, but for some reason Confederacy of Dunces comes to mind. Maybe just because it's one of the funniest books I've ever read. posted by gwint at 4:30 AM on October 1, 2011
Little Green Men and other books by Christopher Buckley posted by martinX's bellbottoms at 6:02 AM on October 1, 2011
The Magicians and the Magician King by Lev Grossman. Ernest Cline's Ready Player One might fit the bill, too. If you go for Douglas Coupland, please for the love of God try his older books first--Generation X and Microserfs. There's an underlying cynicism to his more recent books like jPod which really undermines the narrative. posted by PhoBWanKenobi at 6:56 AM on October 1, 2011 [1 favorite]
There's one American author that I'm totally blanking on. One of his most popular books was kind of a parody on Jesus. Like about his best friend or something. Christopher... something... really blanking.
You may enjoy Gary Shteyngart's SuperSad True Love Story -- which involves a parody of pop culture gone awry, set in a near-future dystopian New York. posted by rdn at 8:33 AM on October 1, 2011
Nthing Coyote Kings! My favorite pet book to recommend on Ask, but haven't had the chance in years. posted by utsutsu at 8:45 AM on October 1, 2011
Coming at the meta and humor from a slightly different direction, I'd suggest Kate Atkinson's early books, especially Emotionally Weird and Human Croquet. Please excuse the terrible title of the former--apparently she was being marketed as chick lit or something--but its subject are the dysfunctional students at a Scottish university and there are plenty of weird digressions into the terrible creative-writing theses they're producing, complete with switches in typography. Atkinson's books manage a poignancy that's entirely unsentimental among the self-referential moves and general unhingedness. posted by MsMacbeth at 10:49 AM on October 1, 2011
Seconding Douglas Coupland, start with All Families are Psychotic or Life After God posted by T.D. Strange at 8:59 AM on October 2, 2011
Lev Grossman's "Magician" books are very funny. Have you read Bill Bryson? His "A Walk in the Woods" is pretty self-conscious, and a load of fun.
Be warned that a lot of these examples will elicit joy from some readers, and grinding of teeth from others: it's definitely YMMV territory. posted by wenestvedt at 9:08 AM on October 3, 2011
I liked The Magicians but it depressed me for weeks after I read it last year. I'm not sure I want to repeat the experience with The Magician King. posted by Memo at 2:40 PM on October 3, 2011
Pat Murphy's trilogy There and Back Again, Wild Angel, and Adventures in Time and Space with Max Merriwell. But the first two won't seem to be relevant until the last provides the context. posted by Zed at 2:28 PM on November 7, 2011
Seconding Chuck Klosterman!
Dave Sedaris also comes to mind, for literate humor.
Also, on a related note, you may enjoy the comedic episodes of This American Life quite a bit. Requires a tad more focus than Community but is usually worth it! posted by brackish.line at 11:39 AM on December 20, 2011
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The Thursday Next series (Jasper Fforde) does a bunch of meta jokes too.
posted by Garm at 9:02 PM on September 30, 2011 [2 favorites]