I have never finished Infinite Jest, though now it's a priority. I know his collections of nonfiction pieces well. Re-reading portions of them this weekend, I saw nothing in them that suggested a hopeless or defeated person (in spite of the weekend's compelling evidence).
The man had an apparently voracious curiosity. He could write about pornography, tennis, politics, movies, dictionaries, seemingly anything. He won a MacArthur Fellowship, a "genius grant." He personified it. He was a genius. He seemed authoritatively smart, but generous.
His sentences and paragraphs could, put mildly, run long. Reading him, too, you were bound to encounter words you'd never seen before. I never found his vocabulary ostentatious, though, because after looking them up they were always exactly the right words.
He was a writer who made me feel total, unmitigated joy while reading. He made the English language do things I'd never imagined while simultaneously making me believe we shared a voice. Like I said, he seemed like a generous man.
As you'd expect for someone whose writing could be so ecstatically fun to read, he could tell jokes, too. Any professional comedian would envy his ability to make people laugh. His essays are loaded with the kinds of sentences and passages that beg to be read aloud. Among my favorites is (from the introduction to an essay called Up Simba, from Consider the Lobster, about John McCain's 2000 presidential campaign):
...the magazine suddenly turned around and called again and said the article was a Go again but that now they wanted me to fly out to NH and start that very night, which (because I happen to have dogs with professionally diagnosed emotional problems who require special care, and it always takes me several days to recruit, interview, select, instruct, and field-test a dogsitter) was out of the question.and (from his description of waiting around to board a cruise ship, from the essay and collection called A Supposedly Fun Thing I'll Never Do Again):
I've decided the perfect description of the orange of the hangar's chairs is waiting-room orange. Several driven-looking corporate guys are talking into cellular phones while their wives look stoic. Close to a dozen confirmed sightings of J. Redfield's The Celestine Prophecy. The acoustics in here have the nightmarishly echoey quality of some of the Beatles' more conceptual stuff. At the Snack Bar, a plain old candy bar is $1.50, and soda-pop's even more... Several Pier personnel with clipboards are running around w/o any discernible agenda. The crowd has a smattering of college-age kids, all with complex haircuts and already wearing poolside things. A little kid right near me is wearing the exact same kind of hat I am, which I might as well admit right now is a full-color Spiderman cap.Obviously things were bad for him. So bad that he didn't think it was important to see how the election turned out or what the new Terminator movie would be like, though he did see the end of the US Open. He was one of the few people outside my friends and family who made me think I am lucky to be alive at the same time as this person.
Here are two of his writings available for free, one about Terminator 2 and one about his love of watching Roger Federer play tennis.