…95 percent of political commentary, whether spoken or written, is now polluted by the very politics it’s supposed to be about. Meaning it’s become totally ideological and reductive: The writer/speaker has certain political convictions or affiliations, and proceeds to filter all reality and spin all assertion according to those convictions and loyalties. Everybody’s pissed off and exasperated and impervious to argument from any other side. Opposing viewpoints are not just incorrect but contemptible, corrupt, evil […] Political discourse is now a formulaic matter of preaching to one’s own choir and demonizing the opposition. Everything’s relentlessly black-and-whitened…. Since the truth is way, way more gray and complicated than any one ideology can capture, the whole thing seems to me not just stupid but stupefying… How can any of this possibly help me, the average citizen, deliberate about whom to choose to decide my country’s macroeconomic policy, or how even to conceive for myself what that policy’s outlines should be, or how to minimize the chances of North Korea nuking the DMZ and pulling us into a ghastly foreign war, or how to balance domestic security concerns with civil liberties? Questions like these are all massively complicated, and much of the complication is not sexy, and well over 90 percent of political commentary now simply abets the uncomplicatedly sexy delusion that one side is Right and Just and the other Wrong and Dangerous. Which is of course a pleasant delusion, in a way—as is the belief that every last person you’re in conflict with is an asshole—but it’s childish, and totally conducive to hard thought, give and take, compromise, or the ability of grown-ups to function as any kind of community.

— David Foster Wallace

All U.S. irony is based on an implicit "I don't really mean what I say." 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 very banal to ask what I mean." Anyone with the heretical gall to ask an ironic what he actually stands for ends up looking like a hysteric or a prig. And herein lies the oppressiveness of institutionalized irony, the too-successful rebel: the ability to interdict the question without attending to its content is tyranny. It is the new junta, using the very tool that exposed its enemy to insulate itself. This is why our educated telephonic friends' use of weary cynicism to try to seem superior to TV is so pathetic.

— David Foster Wallace

Almost anyone who loves tennis and follows the men’s tour on television has, over the last few years, had what might be termed Federer Moments. These are times, watching the young Swiss at play, when the jaw drops and eyes protrude and sounds are made that bring spouses in from other rooms to see if you’re OK.

— David Foster Wallace

... A lobotomy involved some kind of rod or probe inserted through the eye socket, the term was always "frontal" lobotomy;but was there any other kind? Knowing that internal stress could cause failure on the exam merely set up internal stress about the prospect of internal stress. There must be some other way to deal with the knowledge of the disastrous consequences fear and stress could bring about. Some answer or trick of the will:the ability not to think about it. What if everyone knew this trick but Claude Sylvan shine? He tended to conceptualize some ultimate, platonic-level Terror as a bird of prey in whose mere aloft shadow the prey was stricken and paralyzed, tembling as the shadow enlarged and became inevitability. He frequently had this feeling:What if there was something essentially wrong with Claude Sylvan shine that wasn't wrong with other people? What if he was simply ill-suited, the way some people are born without limbs or certain organs? The neurology of failure. What if he was simply born and destined to live in the shadow of Total Fear and Despair, and all his so-called activities were pathetic attempts to distract him from the inevitable?...

— David Foster Wallace

A manual for how to build a mentally ill child

— David Foster Wallace

Am I a good person? Deep down, do I even really want to be a good person, or do I only want to seem like a good person so that people (including myself) will approve of me? Is there a difference? How do I ever actually know whether I'm bullshitting myself, morally speaking?

— David Foster Wallace

AN ACADEMIC DEFINITION of Lynching might be that the term "refers to a particular kind of irony where the very macabre and the very mundane combine in such a way as to reveal the former's perpetual containment within the latter." But like postmodern or pornographic, Lynching is one of those Porter Stewart-type words that's ultimately definable only extensively-i.e., we know it when we see it. Ted Bundy wasn't particularly Lynching, but good old Jeffrey Dahmer, with his victims' various anatomies neatly separated and stored in his fridge alongside his chocolate milk and Shed Spread, was thoroughgoing Lynching. A recent homicide in Boston, in which the deacon of a South Shore church reportedly gave chase to a vehicle that bad cut him off, forced the car off the road, and shot the driver with a high powered crossbow, was borderline Lynching. A Rotary luncheon where everybody's got a comb-over and a polyester sport coat and is eating bland Rotarian chicken and exchanging Republican platitudes with heartfelt sincerity and yet all are either amputees or neurologically damaged or both would be more Lynching than not.

— David Foster Wallace

An ad that pretends to be art is -- at absolute best -- like somebody who smiles warmly at you only because he wants something from you. This is dishonest, but what's sinister is the cumulative effect that such dishonesty has on us: since it offers a perfect facsimile or simulacrum of goodwill without goodwill's real spirit, it messes with our heads and eventually starts upping our defenses even in cases of genuine smiles and real art and true goodwill. It makes us feel confused and lonely and impotent and angry and scared. It causes despair.

— David Foster Wallace

And it never even occurs to them their certainty that they are different is what makes them the same.

— David Foster Wallace

And I was -- this is just how I was afraid you'd take it. I knew it, that you'd think this means you were right to be afraid all the time and never feel secure or trust me. I knew it'd be 'See, you're leaving after all when you promised you wouldn't.' I knew it, but I'm trying to explain anyway, okay? And I know you probably won't understand this either, but --wait-- just try to listen and maybe absorb this, okay? Ready? Me leaving is not the confirmation of all your fears about me. It is not. It's because of them. Okay? Can you see that? It's your fear I can't take. It's your distrust and fear I've been trying to fight. And I can't anymore. I'm out of gas on it. If I loved you even a little less maybe I could take it. But this is killing me, this constant feeling that I am always scaring you and never making you feel secure. Can you see that?

— David Foster Wallace