Infinite Jest

David Foster Wallace's relentless Door Stopper of a novel, first published in 1996. Infinite Jest takes place in the not-too-distant future, around the Enfield Tennis Academy and the neighboring Ennet House Drug and Alcohol Recovery House (redundancy sic) in suburban Boston. Before he died, James Incandenza, founder of the ETA and film auteur, created a movie so mesmerizingly entertaining that the master copy is being sought as a weapon by Canadian terrorists and the US government. Dealing with issues like the nature of the self, family, emptiness and absence, addiction and recovery, and the minutia of tennis, there's just no way to adequately summarize this massively complex novel here. With nearly 100 pages of end notes, this may be one of the only novels for which you will need to use two bookmarks simultaneously.

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This book provides examples of:

 * Accidental Athlete: The older brother in the family starts out playing tennis, and is really good at it, but in college, he tries out for the football team, only to find that he isn't big enough. As he is leaving the try-out, he punts a football, and the coach realizes he is a really good kicker
 * Addiction Displacement: All of the characters to some extent, but none so horrifying as evening constitutionals.
 * The Alcoholic: James O. Incandenza, Jr. (and Sr.), and a few others besides. Junior seemed to be functioning until shortly before his death, though.
 * All There in the Manual: The book's extensive end notes.
 * Alternative Calendar: In DFW's alternate future, even the names of years have been sold for ad space, leading to such confusing chronological reference points as the Year of the Depend Adult Undergarment and the Year of the Purdue Wonderchicken
 * Anachronic Order: The book starts sometime after the end of the plot, and then cycles back through the year or so leading up to that point. And then you're still not quite sure what happened.
 * And I Must Scream: The fate of Hal Incandenza. That's not a spoiler, it's the first chapter.
 * Author Appeal: David Foster Wallace was a pretty good tennis player in his youth, reaching the top levels of junior tennis in high school. It makes some sense that he'd set some of the novel around a tennis academy.
 * Author Avatar: In fact, Hal Incandenza resembles Wallace himself in his youth to some degree. However, the trope is not used in any way beyond simply existing. Indeed, although his empathy for the character is obvious, one would have to have read Wallace's biography and probably some of his nonfiction (or, um, this entry) to even see the actual similarities.
 * Also, James' work is described once or twice as deliberately abstruse and unentertaining, seeming in some ways hostile to the audience. Does This Remind You of Anything
 * Author Vocabulary Calendar: A novel this size, one could be forgiven for assuming this out of hand, but nope. Aside from some Future Slang and tennis terminology (which is always explained), conversational English reigns throughout.
 * Admittedly, there are a fair number of oddball ten-dollar words tossed in...but only where it would suit the voice of the viewpoint character, in which case it's seamlessly blended into ordinary conversational English.
 * The Beautiful Elite: Joelle Van Dyne,.
 * Best Served Cold: Pemulis' philosophy when it comes to revenge.
 * The Big Guy: Don Gately
 * Big Screwed Up Family: The Incandenza family.
 * Brick Joke: Gately's toothbrush prank on the ADA in the hat comes back hilariously only about 800 pages later.
 * Hilariously might not be the right word, considering the effect of said prank on the ADA's wife.
 * Brown Note: The eponymous "Entertainment" is a short film apparently so captivating that anyone unfortunate enough to see it will become hopelessly and irreversibly addicted to it, wanting to do nothing but continue watching it again and again, even at the cost of physical harm to themselves.
 * Calvin Ball: One of the courts at the ETA is intricately painted with a map of the Earth and all its nations. Its only use is for a training game of nuclear geopolitics, which has become something of an Academy tradition. True to the trope, all that is made explicitly clear is that nuclear strikes are represented by serving tennis balls onto the map; the rest of the rules are stated to be so complex that they can only be understood through total memorization.
 * This part of the book has actually been adapted as a music video, for "The Calamity Song" by The Decemberists.
 * Canada Eh
 * Cold Blooded Torture:.
 * College Radio
 * Crapsack World
 * Crosswicking: In-universe, Infinite Jest is a film so mesmerizing that the U.S. government is interested in weaponizing it.
 * Dead Person Conversation: The wraith of James Incandenza may be visiting one or more of the other characters.
 * Department of Redundancy Department: The Ennet House Drug and Alcohol Recovery House (sic).
 * Disappeared Dad
 * Door Stopper: This baby clocks in at a mean 1079 pages, including the (required) appendix. It's so intimidating that an on-line support group was formed to help those who'd always meant to but never quite managed to finish it, a full thirteen years after its initial publication.
 * Double Agent: Remy Marathe is actually a "quadruple agent"....
 * Elaborate University High: Enfield Tennis Academy
 * Empty Shell: The fate of victims to "The Entertainment".
 * Evil Cripple: Les Assassins des Fauteuils Rollents, a.k.a. The Wheelchair Assassins of Southern Québec.
 * Eye Scream:.
 * Fantastic Drug: The incredibly potent DMZ. Described as "acid that has itself dropped acid", its hallucinogenic properties are rumored to be so powerful that it may cause the user to permanently lose the ability to communicate with the rest of the world. Hal and Pemulis are still eager to experiment with it.
 * Fictional Political Party: President Gentle's Clean US Party. Yes, as in "CUSP."
 * Footnote Fever: The story proper ends at page 981, with the remaining 96 pages being taken up by 388 end notes, some of which are several pages long, and a few more which have their own footnotes and/or end notes. Readers quickly figure out that the only way to avoid permanent damage is to use two bookmarks: One for your place in the main text, and the other for where you are in the end notes.
 * Fun With Acronyms: In spades. For starters, America, Canada, and Mexico have merged to form the Organization of North American Nations, or O.N.A.N. Rest assured that the term 'O.N.A.Nistic' appears at some point.
 * Also the 'Union of the Hideously and Improbably Deformed' (UHID), whose members wear a face-concealing veil in public.
 * Let's not forget the Wounded, Hurting, Inadequately Nurtured but Ever-Recovering Survivors (WHINERS)
 * Future Slang: Inspired by the creation of The Great Concavity/Convexity, the word "map" has come to mean "face," and so to "erase someone's map" has come to mean murder or horrible disfigurement, while "erasing your own map" refers to suicide.
 * There's also local Boston slang, some of which (like "mitt" for "meter") is almost certainly fictional, while some (like "eating cheese" for "ratting someone out") might or might not be.
 * Gainax Ending
 * Grammar Nazi: Avril Incandenza, in both the best and worst possible ways.
 * Hal grows up to be Grammar Nazi Jr.
 * The Grotesque: Mario, the middle Incandenza child, is bradykinetic, leptosomatic, macrocephalic, homodontic, and suffers from familial dysautonomia, among other ailments. He's also one of the kindest and most sympathetic characters in the book.
 * How We Got Here: Subverted, since the reader is never told the exact nature of "here".
 * Inspirationally Disadvantaged Mario Incandeza's optimism in the face of a long list of disabilities is nearly this, but without being too Narmy.
 * Intoxication Ensues: One of Pemulis' preferred methods for exacting revenge is spiking your food or drink with something mind-altering. The guys also consider spiking the cooler at a big event with the DMZ, but think better of it.
 * Jerkass: Orin Incandenza.
 * Jigsaw Puzzle Plot: There's no picture on the box, and at least half of the pieces seem to be missing, but since nobody actually knows how many pieces there are supposed to be...well, good luck, kid.
 * Lady Drunk: Gately's mother, for one.
 * Le Film Artistique: Much of James Incandenza's filmography.
 * Literary Allusion Title: Alas, poor Yorick....
 * Loads and Loads of Characters
 * Mind Rape: The last time we see.
 * Military Time: Wallace seems to have preferred it, and all the characters use it without a second thought.
 * Mushroom Samba: gets dosed without his knowledge, and this is hinted as one possible cause for  as well.
 * My Secret Pregnancy: Avril Incandenza was not aware she was pregnant with Mario until his premature and surgically assisted birth.
 * Nice Hat: Pemulis is almost never without his yachting cap, the lining of which can be detached to store drugs.
 * No Ending: There is something of a gap between the ending of the story and the prologue, which chronologically is also the epilogue, so most of the plot lines are left dangling.
 * Our Presidents Are Different: President Johnny Gentle, a former lounge singer and rabid germophobe, also responsible for turning a vast swath of Northeastern US/Southeastern Canada into a hazardous waste dump, falls somewhere between President Buffoon and President Lunatic.
 * Really Gets Around: By most reports, Avril Incandenza would sleep with anything male, except for her husband.
 * Orin counts as well.
 * Serious Business: Tennis. But this is a tennis academy, after all.
 * Shout Out to Shakespeare
 * Shown Their Work: Contains more than the average human will ever want to know about tennis.
 * Not to mention pharmaceuticals, in the end notes.
 * Show Within a Show: Mario's puppet show, several excerpts from James O. Incandenza's filmography.
 * So Beautiful Its a Curse: It's hinted that this is the real reason Joelle wears a veil.
 * Stepford Smiler: One aspect of Avril Incandenza. Someone tells a story about how when Orin accidentally killed her dog, she went on calmly acting as though nothing had happened in order not to upset him.
 * The Metric System Is Here to Stay: Wallace had a definite preference for metric units, and in his universe, they've become standard in the U.S. (probably as a result of ONANite integration).
 * Title Drop: The "Entertainment" is also titled Infinite Jest.
 * Twenty Minutes Into the Future: It's never specified, but from some references to characters' ages and the approximate beginning of "Subsidized Time," you can extrapolate that the plot takes place sometime in the first decade of the 21st Century, 10-15 years after the book was published. There is a reference to "the Limbaugh administration."
 * And later a reference to a poster of Limbaugh "from before the assassination" (929).
 * Unreliable Narrator:
 * Video Phone: Mockingly Discussed in a passage which describes how widespread videophone use made people increasingly concerned about their physical appearance, leading to most people wearing elaborate masks whenever they used the phone (and, later, just switching back to normal phones).
 * Whole Episode Flashback
 * Worlds Most Beautiful Woman: Or rather the Prettiest Girl Of All Time. Meaning Joelle. This is important.
 * Write What You Know: As mentioned above, Wallace was an accomplished tennis player.
 * Zeerust: Although the popularity of cartridge rental anticipates Netflix, Wallace didn't seem to predict that people would rather do away with physical media altogether and just stream their entertainment.