It has become a commonplace in the literary community to call Wallace a genius. This seems to occur in part because he won a MacArthur "genius" grant, which many writers covet, and in part because he wrote about math, which many writers fear. Mostly, though, the plaudit stuck because Wallace was smart and articulate and had the enviable quality of finding everything interesting. But in truth, his appeal lies more in his honesty than his intellect; it is less that his observations were profound than that others lacked the self-scrutiny or courage to voice them. Throughout the road trip, Wallace spoke with disarming candor about difficult issues: a suicide scare in college, an almost crippling fear of how others perceived him, difficulty finding love. No contemporary writer discussed despair and loneliness with such frankness.
DFW was hyper self-aware, but also almost painfully shy and self-conscious and always self-deprecating — Almost every important answer DFW gives is couched with a sort of disclaimer that he's aware how what he's saying could be misinterpreted in print.