The interesting thing is why we're so desperate for this anesthetic against loneliness.

And make no mistake: irony tyrannizes us. The reason why our pervasive cultural irony is at once so powerful and so unsatisfying is that an ironist is impossible to pin down. All U.S. irony is based on an implicit "I don’t really mean what I’m saying." So what does irony as a cultural norm mean to say? That it’s impossible to mean what you say? That maybe it’s too bad it’s impossible, but wake up and smell the coffee already? Most likely, I think, today’s irony ends up saying: "How totally banal of you to ask what I really mean.

....there is an ending [to Infinite Jest] as far as I'm concerned. Certain kind of parallel lines are supposed to start converging in such a way that an "end" can be projected by the reader somewhere beyond the right frame. If no such convergence or projection occured to you, then the book's failed for you.

I often think I can see it in myself and in other young writers, this desperate desire to please coupled with a kind of hostility to the reader.

I miss everyone. I can remember being young and feeling a thing and identifying it as homesickness, and then thinking well now that’s odd, isn’t it, because I was home, all the time. What on earth are we to make of that?

John McEnroe...was arguably the best serve-and-volley man of all time, but then McEnroe was an exception to pretty much every predictive norm there was. At his peak (say 1980 to 1984), he was the greatest tennis player who ever lived-the most talented, the most beautiful, the most tormented: a genius. For me, watching McEnroe don a blue polyester blazer and do stiff lame truistic color commentary for TV is like watching Faulkner do a Gap ad.

Ideally, each piece of art's its own unique object, and its evaluation's always present-tense.