Context: There is an ever-growing body of work continuing the argument for play as a pedagogical resource that supports the learning of the youngest learners; despite this, there continues to be little evidence play has been considered as such in teacher education. Research Focus: The study sought to understand the role of play and playful pedagogies in a school-based literacy education course within a teacher educator program. Setting: Research was conducted in a school-based literacy education course housed in an urban school in the Midwest. Participants: Preservice teachers enrolled in literacy education coursework at a midsized urban institution of teacher education. Research Design: Data utilized in this study comes from a multiple case study using a practitioner inquiry lens. Data Collection and Analysis: Data collection occurred over five semesters (Spring 2016-Spring 2018). Types of data included mid- and end-of-semester interviews, audio and video recordings of rehearsals, video recording of enactments, and a variety of artifacts produced by preservice teachers within the course. Findings: Play, utilized within the context of a literacy education course, promoted the development of complexity tolerance: an ability to entertain the variables that may impact their teaching, even those they had not thought of. Recommendations: This complexity tolerance supported preservice teachers in being able to respond to student learning in the moment, deviate from instructional planning when necessary, and interrogate their own educational histories. It is a powerful pedagogical tool to support preservice teacher development when intentionally invoked in teacher education coursework.