Literary critics, like those in the Legacy of… volume, have offered a slew of explanations for how Wallace attempts to transcend the problem he so eloquently diagnoses. Marshall Boswell’s account suggests that Wallace “opens the cage of irony by ironizing it, the same way he uses self-reflexivity to disclose the deceptions at work in literary self-reflexivity.” The double negative becomes an affirmation. Westward overcomes its influences, and Wallace “declares himself ready to build a genuine funhouse that will rival that of his predecessors and assuage, rather than re-present, loneliness.” For Boswell, Infinite Jest is that funhouse. Samuel Cohen, agrees with Boswell that Westward is Wallace’s effort to break free of his postmodern influences. But he disagrees with Boswell about whether he succeeds. Instead, for Cohen, it is precisely Wallace’s distinctively millennial anxiety over the futility of overcoming the burden of history, that makes him speak so loudly to a generation of anxious readers who similarly find themselves “in the middle of things,” overwhelmed by the past, uncertain about the future.

A.O. Scott adds to these characterizations the idea that Wallace's “meta-ironic” tact intends to “make his fiction relentlessly conscious of its own self-consciousness, and thus produce work that will be at once unassailably sophisticated and doggedly down to earth.” But Scott is less sanguine about the outcome of Wallace’s meta-recursion than Boswell:

The effect, and perhaps the intention, of his habit of turning his jokes around on himself is to short-circuit criticism, much in the way that the hideous men’s confessions of their own dishonesty [in Wallace’s Brief Interviews with Hideous Men] are meant to make them appear, ultimately, sincere.

In Scott’s view, this “heavily defended discourse,” has the effect of preventing communication, just as the “impeccably logical seductions and repulsions” of Wallace’s hideous men are “designed to protect them from the illogical messiness of genuine human contact.”[14]  Scott’s basic contention is that Wallace, as a writer, is flagrantly guilty of precisely the same honesty-as-a-means-of-conceit thing he diagnoses in Brief Interviews. When Scott asks whether Wallace’s work represents an “unusually trenchant critique” of what Christopher Lasch called “the banality of pseudo-self-awareness” or “one of its most florid and exotic symptoms,” his answer is, perhaps predictably, both.