Ludwig Wittgenstein and Michael Oakeshott are often labeled conservative thinkers, and taken to theorize rigid limits to individual agency and criticism. Tracing several modes of affinity between the work of Wittgenstein and Oakeshott, one can recognize the conventionality and rule-governed character of linguistic practices and yet affirm a deeply individualistic account of agency and action. Each thinker respectively characterizes the individual as located within a context of action that is richly structured by intersubjective rules and practices. Yet each also recognizes an ineluctable dimension of individuality and contingency to action that surpasses mere rule following or the reprise of conventional practice. The very situatedness of the individual agent within a framework of linguistic practices shared with others provides the friction that enables individual criticism and transgressive political action. Wittgenstein and Oakeshott thus present a perspective on political agency and criticism that is a salient alternative to both conservative and radical views.