In the past few years, advances in big data, machine learning and artificial intelligence have generated many questions in the intellectual property field. One question that has attracted growing attention concerns whether algorithms can be better deployed to promote fair use in copyright law. The debate on the feasibility of developing automated fair use systems is not new; it can be traced back to more than a decade ago. Nevertheless, recent technological advances have invited policymakers and commentators to revisit this earlier debate. As part of the Symposium on "Intelligent Entertainment: Algorithmic Generation and Regulation of Creative Works," this Article examines whether algorithms can be better deployed to promote fair use in copyright law. It begins by explaining why policymakers and commentators have remained skeptical about such deployment. The article then builds the case for greater algorithmic deployment to promote fair use. It concludes by identifying areas to which policymakers and commentators should pay greater attention if automated fair use systems are to be developed.