The connections people have drawn to The Entertainment and Hamlet are great. In fact it seems an almost direct reference to The Entertainment's effects, and I can't believe that that didn't occur to me earlier.
As to Hamlet, I think we're seeing the theme of inaction being taken to an extreme here. But just as in Hamlet, it's not really all the fault of our protagonists: part of it is the cause of society and of the previous generations. Hal's essay itself deals with the progress from one decade to the next, showing that heroes didn't suddenly become less active and forward, but rather became so as society gradually came to expect them to be. The effect of one generation on the next is especially apparent in the B.S. 1960 section with J.O.I.'s father. Here we see the parents of one generation causing the next to act how it will, just as Hamlet—who really only wanted to return to school in Wittenberg and live his own life—fell into conflict and tragedy because his uncle killed his father and his father's ghost told him to seek revenge. The pressures were too much and he fell to inaction. Admirable, but it didn't solve any problems. In IJ, we see characters finding the pressures being put on them by previous generations (e.g., to be great at tennis) to be too much, so they, too, fall to inaction (e.g., by doing drugs). Not as admirable, and certainly not solving any problems.
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