I’m still chugging along through Infinite Jest.
Adam Kirsch has written one monster review  in The New Republic of The Pale King, Fate, Time, and Language: An Essay on Free Will, both by David Foster Wallace, and Although Of Course You End Up Becoming Yourself: A Road Trip with David Foster Wallace, by David Lipsky.
It’s a meandering review, and while its conclusion is not particularly unusual (“One of the many things to mourn about Wallace’s death is that we will never get to know the writer he was striving to become.”), there are many intriguing observations along the way:

This argument is translated into fictional terms in the early story “My Appearance,” from Wallace’s collection The Girl with Curious Hair, which appeared in 1989. The story concerns a middle-aged, moderately successful TV actress who is making an appearance on David Letterman’s talk show. Her challenge is to find a way to communicate sincerely in the face of Letterman’s sneering irony, which to Wallace is the epitome of TV-bred cynicism. A friend tells her that the only way to cope is to out-Letterman Letterman: “Laugh in a way that’s somehow deadpan. Act as if you knew from birth that everything is clichéd and hyped and empty and absurd, and that that’s just where the fun is.”
Wallace dreads this kind of irony, which poisons communication and makes displays of emotion look ridiculous. He dreads it on civic grounds, of course; but he also sees cool knowingness as a deadly threat to his own literary genius, which is essentially sentimental and melodramatic. (“There’s never been a time in serious art more hostile to melodrama,” he complained to Lipsky.) That is why Wallace is exercised by the ironic self-consciousness of postmodern fiction, in much the same way that he is disturbed by David Letterman. Lost in the Funhouse can hardly be held responsible for “a great stasis and despair in U.S. culture”—for one thing, not enough people have read it. But in “Westward,” Wallace offers a novella-length attack on the metafictional gamesmanship of Barth’s story: “You want to get laid by somebody that keeps saying ‘Here I am, laying you?’ Yes? No? No. Sure you don’t. I sure don’t. It’s a cold tease. No heart. Cruel. A story ought to lead you to bed with both hands.”
In his hostility to pop-cultural irony, Wallace was (ironically, perhaps) in agreement with the best pop culture of his time. Many people have observed that Wallace’s trademark look—the bandana, lank hair, and stubble that appear in his author photos, and made him one of the most recognizable writers of his time—evoked the grunge style of Kurt Cobain, the lead singer of Nirvana, whose suicide in 1994 was a mythic moment for Generation X. When Lipsky, who was profiling Wallace for Rolling Stone, asked him the obligatory questions about his taste in music, he described Cobain’s songs as “absolutely incredible. But unbelievably painful. I mean if you, you know, all the stuff that I was groping in a sorta clumsy way to say about our generation? Cobain found, Cobain found incredibly powerful upsetting ways to say the same thing.”
The famous lyrics of “Smells Like Teen Spirit”—“I feel stupid and contagious/Here we are now, entertain us”—could be used as an epigraph to Wallace’s essay on television, and even more appropriately to Infinite Jest. Cobain’s sullen parody of alienation used irony to defeat irony, much as Wallace, in “Westward,” used metafiction to defeat metafiction. And the young novelists who followed in Wallace’s wake—Jonathan Safran Foer, Dave Eggers, and Zadie Smith, to name the most prominent—have shared his righteous refusal of irony. They believe that literature should be positive, constructive, civically engaged, a weapon against alienation. Jonathan Franzen, who was Wallace’s close friend and has staked repeated public claims to his legacy, told The Paris Review that the two of them shared a philosophy of fiction: “The point of agreement that he and I eventually reached was the notion of loneliness: that fiction is a particularly effective way for strangers to connect across time and distance.”

The review, of which this is only one small part, is well worth reading in full for anyone interested in Wallace’s fiction or interested in the themes that he explored in that fiction.