Recent scholarship has suggested that evaluation is becoming increasingly institutionalized and entrenched in problematic discourses, leading to a narrowing of possibilities for evaluators to contribute to meaningful social change. At the same time, evaluation approaches which are grounded in values of social justice and equity are receiving greater attention within the field. Given these two seemingly contradictory trends, this research was conducted to better understand how we might engage in evaluation practice which is cognizant of and resistant to dominant social discourses while at the same time working actively to promote a more free, just, and equitable society. This dissertation comprises three interconnected studies of how critical theory has been and might in the future be applied to enhance evaluation theory and practice. The first study is a review of evaluation literature which finds that while sparse, critical theories have been used to advance critiques of evaluation's entanglement in ideology and discourse; to advance forms of feminist, decolonizing, and culturally responsive practices; and to elaborate a participatory and educative form of critical evaluation practice. In the second study, findings based on analysis of interviews with evaluation scholars and practitioners suggest that critically-engaged evaluation practice requires deliberation and dialogue with stakeholders about the ways that programs shape--and are shaped by--systems of power, and that while critical inquiry may not be prioritized within the current evaluation marketplace, opportunities exist to push both localized practice and the field in more critical directions. Finally, the third paper engages in a conceptual analysis of how specific modes of critical practice may be applied toward fundamental issues of evaluation, suggesting ways that critical theories challenge common notions of social programming, knowledge construction, values, and use within the field. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]