In 'An Essay on Criticism,' Alexander Pope intends to propose an ideal relationship between wit and judgment: both derive their light from Nature, and wit must yield to the reign of judgment or critical rules because it may transgress the Nature-set boundary, fly without restraint, and consequently disturb the harmony in Nature. However, Pope neither renders wit and judgment in a consistent and stable relationship, nor submits his wit to judgment. In terms of the Bakhtinian dialogism, both wit and judgment work like the centrifugal force and the centripetal respectively, and Pope's artistry demonstrates their dialogic relationship—not that wit must always follow judgment, but that both must moderate each other in continual negotiation. In the following discussion, I will first of all discuss the features of wit, and study the voices of the attackers and the defenders of wit before Pope. In the next section I will point out Pope's incorporation of those contradictory voices: sometimes he exalts judgment above wit in importance, but sometimes he glorifies wit more than judgment. It is impossible to judge 'objectively' in such a condition; moreover, the fluidity of taste and the unreliability of reason also contribute to this impossibility. His wit 'betrays' reason and judgment so much as to upset the stability of the Great Chain of Being. Although Pope claims to follow reason, he is also fascinated by Timotheus's manipulation of audience's emotion, and he may criticize with 'the spontaneous overflow of powerful feelings.' Wit in Pope's artistry works indeed as a subversive, norm-defying force; its continual conflicts with judgment manifests that dialogue, not Nature, truly governs their relationships.