To all the people who encouraged me to read David Foster Wallace--who assured me that his essays were unsurpassed examples of the form; who dragged me to the DFW shelf at Powell's and said "My goal in life is to be half as good a writer as him"; who sat in a corner of my living room last fall and confessed how torn up you were about his death...
You were right, all of you. I'm only sorry that it took me this long to follow your advice! After reading Consider the Lobster, I'm joining your ranks in the Wallace-cult. (I've noticed that, at least in San Francisco, it is impossible to find Wallace's books in used bookstores--suggesting that the people who buy his books fall in love and cannot be induced to part with them.)
"Authority and American Usage," in which Wallace ostensibly reviews a new usage dictionary but really summarizes the whole history of Prescriptivism vs Descriptivism (in linguistics) and makes a complex argument in favor of prescriptivism, is probably my favorite essay in the collection... one of my favorites of all time. I love that it is so shamelessly an essay, as opposed to an article or a piece of reportage--that is, it has a thesis and a clearly organized argument running through it, and continually refers to its own structure. Because of this, and because Wallace spends a lot of the essay discussing how rhetorical and argumentative strategies function, it is really a meta-essay, which is just terrific, and quite educational. Seriously, this should be required reading in college. If only for the way that Wallace rails against the shoddy and obfuscatory quality of most academic prose.
This collection doesn't include Wallace's famous "cruise-ship essay," but it does have other articles that rely on his powers of observation and eye for the absurd: "Big Red Son," about the porn industry's annual awards ceremony, and "Up, Simba" (qtd. here) about John McCain's 2000 presidential campaign. These essays combine detailed "you are there" descriptions of the people and things that Wallace encounters, with thoughtful reflections on the significance of all of this crazy stuff--an extremely strong combination. The tone of the porn essay is incredulous, but not shocked: Wallace is not trying to create a moral panic, but simply to depict this subculture and the way it resonates in the culture at large.
As for the title essay, it seems like Gourmet magazine commissioned Wallace to go to another wacky corner of America (the Maine Lobster Festival) and describe the scene there. What they got, after some throat-clearing scene-setting, was a not-at-all-wacky, dead-earnest inquiry into whether it is ethical to boil lobsters alive and eat them. He doesn't come to any conclusions in this one, admitting that the issues are too much even for him. Still, it--and several of the other pieces--shows how concerned Wallace was with morality. His deepest desire is for people to approach life with "a democratic spirit" of fairness and sincerity.
Wallace was a great cultural commentator, and when people in the future want to know what life was like in millennial America, they should turn to these essays. Because America in the early 21st century is full of contradictions, and Wallace gets that, and writes about it, better than anyone. And these essays show that he, himself, was a contradiction. A sloppy-looking, bandanna-wearing dude who was also proudly nerdy and pedantic when it came to the English language. An acclaimed highbrow littérateur with a secret penchant for reading ghostwritten autobiographies of sports stars. A writer whose work was all about tracing his self-conscious and convoluted mental processes, but who could also be remarkably self-effacing (in several of these essays he never refers to himself as "I," but only as "your correspondent").
And I guess that's why his death hurts so much. It seemed that, in Wallace, we had someone who clearly understood the contradictions of American life, and could explain them to us, and despite being self-conscious and self-doubting so much of the time, had learned to live with these contradictions. But now, we think "If Wallace couldn't cope with the contradictions of life--what hope do the rest of us have?"