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Sherlock Holmes is famed as master analyst and defender of the common man within modern Enlightenment order, embodying the triumph of positive reasoning, a figure of idealized modern identity in a combination of rational power and social stability. However, Holmes as Enlightenment champion rests upon a dark foundation—of personal alienation, a tendency toward violence, and a striking addiction to drugs. Only with an understanding of the challenges and compromises that Holmes represents can we take full measure of this figure who haunts our cultural imagination, one forever balanced on the razor's edge of Enlightenment and barbarism, of cultural progress and its opposite. This article takes a broad look at this complexity in Holmes as it crystallizes across the cannon and reconsiders the detective as a figure of critical ambiguity, one who invites consideration of Enlightenment complication and uncertainty, rather than any simple celebration of its efficacy and power.