Originally published in Brief Interviews With Hideous Men*. Personal enjoyment rating (out of 100): 75.
[Heavily footnoted story; for the sake of quoting, I've simply put the footnotes in brackets.]
He had inserted the quarter, or was about to; the silvered disc clung to those final pale inches of his fingers, fleshy whorls brushing metallic ridges, the token more than half-spent, quivering now (the hand, not the object) from the vice-like effort with which he held to those last precious seconds between deposit and purchase [the irony was not lost to him, the Player, for it was the purchase of those ever-slickening betrayers of fingers with which he prolonged the physical purchase]. Mean-mean-meanwhile, the other hand, the Claw, gripped, with its not inestimable oligodactylic strength, the vulcanized bulb of a joystick [joy, and yet it was a fist you made to hold it, he mused, the quarter slipping another millionth of an inch], lethargically sweeping it through the paces as if it were an inverted miniature music-box dancer (Beauty), and the Claw (Beast) the filigreed gear spinning along to the empty orchestra pinging through the speakers.
The novelty of this story, itself originally disseminated in novel (literal and figurative) form, has always struck me as showing a side of Wallace's playfulness -- despite the tragic ending, involving the inevitable asphyxiation of the boy's baby brother, trapped within the machine -- that we don't often see in his other work. The wordplay is admittedly more showy than in Wallace's other shorts, particularly by the final, terser, more removed stage of his writing, but in many ways, that's a necessity of the theme and setting -- an arcade on its final legs -- and one whose gaudiness helps to reflect the disfigurements of the characters and machinery (all of which, it can be said, are stand-ins for the larger city itself, in the midst of a depression that may remind modern readers of Detroit).
There's also something interesting about the time-compression of this short, which we'll see in more detail as we move on to Oblivion, for while the story focuses, elaborately so, on the insertion of this coin (and you could point out what this represents about limits, as Wallace continues to tease the quarter's slow drop time and time again), I believe that only a few seconds actually pass: "The screen blinkers on-and-off through the pixels so quickly now, so quickly that he does not notice; the rare moment where his own blink falls out of sync with the device unsettles him in a way that he cannot explain, all the more for his unawareness of it." All of these thoughts, then, are subconscious, a representation of the millions of unacknowledged things that happen each second, a point that reflects poorly upon the time that the boy is wasting playing such games in the first place. More importantly, outside of this time, there's the dead brother (and, outside, the dead city): we may not read of his fate until those final lines, but it's obvious from the timeline given that he's dead from the start of the story. Some things we realize too late; we cannot change our course in the middle.
What holds the story back, for me, is when Wallace leaves humanity too far behind and focuses on the intricate machinery itself, leaving behind the comparisons between flesh and steel. His technical vocabulary starts to get to me, too; only in Infinite Jest's infamous description of the radio station have had I look up so much -- and for what? Perhaps we're meant to feel the disconnect; that is, perhaps Wallace doesn't want us to define these words, he wants us to know that they exist (which is why he doesn't make them up) and to suffer from knowing how much we do not know about the simplest things. Or, not suffer, exactly, but to empathize with a pain -- a gap -- that we all share. If there is this much to not know about simple devices, imagine, then, how much we do not know about machines as complex as one another, machines that we cannot fix by simply inserting additional quarters.
*Available only as a promotional insert found within special copies of the hardcover's first edition print run.