What was once an interdisciplinary project built upon Marx’s critique of the political economy, being critical has emerged as an essential skill in an increasingly polarizing world. Critical Studies and the “Crits” in educational research have developed incisive approaches to interrogating systems of power and offered analytical frameworks to explain institutional arrangements, including their failures. This chapter builds upon the genealogy of critical scholars in education to challenge facile critiques that reduce being critical either to simply ideological status or an unqualified rejection of opposing ideas and thinkers. We establish that to foster truly a critical perspective, critical studies in education must engage in the productive struggle with opposing logics to avoid reifying one’s position or becoming undialogical while claiming to be critical. A critical perspective views the world as inherently entangled. Amidst this interconnectedness, “critical” thinkers who disengage from the opposing “other” negate the productive value of conflict. As such, perspectives are only part and parcel to the totality of the greater whole. If perspectives are incomplete, then engaging the “other” offers an opportunity to generate critical knowledge as part of a larger, if not also critical, perspective. Acknowledging the incompleteness of understanding invites Edward Said’s sense for the contrapuntal by holding the tensions between conflicting perspectives as an intellectual practice of co-existence.