Written by: Lance Carmichael, CC2K Staff Writer
Infinite Jest – This is the doozy. 1,079 pages, including 96 pages of dense footnotes. His magnum opus, and considered by some (myself included) but not all (obviously this is a ridiculously grandiose statement) to be the best novel ever written. Certainly not for the faint of heart, though. Wallace stacks the deck against the aforementioned faint-hearters early by opening with a series of seemingly unrelated, stylistically diverse chapters out of chronological order. Sack up, and plow through it, but not too fast—the opening hundred contain some of his best writing, including a chapter about a guy sitting in his apartment waiting around for an acquaintance to deliver $1,250 worth of pot that completely knocked me flat. I never knew literature could do what that chapter does.
Don't worry–if you stick with it, Infinite Jest all comes together and makes a sort of sense. The three basic plot strands are about a prodigiously talented and dysfunctional family at an elite tennis academy, a group of last-chance addicts at a halfway house going through AA, and a fringe group of Canadian terrorists hunting for a movie rumored to be so entertaining it actually kills you. It’s a hilarious novel, but deeply sad—and it will be impossible to set DFW’s suicide aside when reading about the characters struggling with crippling depression and, yes, suicidal thoughts. It’s about living in a nation that’s entertaining itself to death, and so much more.
A Supposedly Fun Thing I’ll Never Do Again – Many readers prefer DFW’s non-fiction to his fiction, and it’s easy to see why. He can write about seemingly any topic—from David Lynch to English usage to the geography of the Midwest’s “tornado alley”—but his best stuff comes when he goes out into “the field” as a reporter at some quintessentially American gathering: a luxury cruise, a State fair, a tennis championship, and so on. This collection is slightly more consistent in quality than Consider the Lobster, but both are essential reading.
Brief Interviews with Hideous Men – Perhaps Wallace at his darkest, which is saying something. But no matter how dark he gets, he always entertains. The twisty self-consciousness mind-bender “The Depressed Person” is obviously going to get a lot of attention now: it follows the warped, incredibly solipsistic and hopeless thoughts of a clinically depressed person who’s mind is chewing itself up so badly she drives even her therapist to suicide. DFW also explores the shadowier recesses of the modern male’s thoughts on sex and females in the titular stories, a series of “interviews” of men with various sexual hang-ups by a presumably female interviewer who’s questions we never get to read. DFW also explores his more experimental side here, with several meta stories that devolve into him, as DFW, lamenting how these stories have gone wrong as he’s written them. Not everything in here works, but I’d say about 85% of it does, and that stuff frequently blows the mind.
Oblivion – Another short story collection (DFW’s last while still alive), Oblivion is rated slightly lower than Interviews only because it’s not quite as consistent. “The Suffering Channel” and “Oblivion” didn’t personally do much for me, but boy oh boy, some of these are as good as it gets. He starts off with “Mister Squishy,” a story (mostly) about a guy who leads product focus groups for market research purposes, written in the depressing argot of that most deeply modern and depressing of professions. “Another Pioneer” is unlike anything else in this wildly diverse writer’s catalog: it’s a recounting of a conversation somebody overheard on a plane about a primitive tribe that was led by a child who could answer any question asked of it, and the tribal shitstorm that ensued. But “Good Old Neon” is what’s going to get the most attention as we come to grips with DFW’s suicide: it’s written from the perspective of a guy who committed suicide, and “Dave Wallace” himself is a character.
Consider the Lobster – Another collection of essays, this one came out a few years ago. You can tell DFW had aged a bit when comparing this to Supposedly Fun Thing: he’s not quite as ruthless and willing to go for the killshot on a subject in many of these. Still, “Big Red Son,” his essay on attending the Adult Video News Awards in Las Vegas (originally written for Premiere Magazine), is perhaps my favorite thing ever written by anyone anywhere, ever. It’s so goddamn funny: please read it. And he's got a long essay on following McCain around on the 2000 primary campaign trail that's (unfortunately) become relevant again.
Broom of the System – DFW’s first novel, and it shows. There’s some gags in here that fall flat, and the “Scooby Doo Ending” (my name for endings where all the characters involved in a story end up converging against all logic on the same place at the same time to wrap things up) is weak, but there’s plenty of good stuff in here, and it’s frequently hilarious. Which is pretty amazing when you consider that he wrote it when he was twenty fucking three years old.
The Girl With Curious Hair – This was DFW’s first collection of short stories, and it’s my least favorite of his books. A lot of the stories feel like they were written in an MFA program—which I think a lot of them were. This is stuff written by a ridiculously talented guy still figuring out his voice, experimenting with a lot of styles, and indulging in some overly cerebral, Inside Baseball kind of literary shenanigans and cross-textual allusions. Still, there are gems to be found… particularly the title story.
Miscellanea – Lastly, there’s stuff that’s not collected in any books at all, but is still really pretty amazing. This essay here is my favorite thing to read when I need a little inspiration to keep writing. His commencement address to Kenyon College is getting mentioned a lot in his obits in the blogosphere. And there’s plenty more. His interviews are deeply thoughtful and provocative—the Howling Fantods is a great resource for finding stuff on the web.