This research study examines my experience as a high school art educator as I  attempted to rethink and remake a high school art foundations curriculum. For this study, I utilized a theoretical framework of complexity thinking as it pertains to the dynamic phenomena of teaching and learning to critically approach and challenge traditional pedagogical approaches to teaching an art foundations course. Processing data collected from two classes over the course of a semester (January-May, 2016), I  utilized a Design-Based Research (DBR) methodology to iteratively examine the effects of a newly designed curriculum whose central focus was to promote the potential benefits of treating contemporary artists as creative role models by examining various aspects of their artistic practices with students. Through the experience of this study, I found that greater success and stronger student engagement could be cultivated in a high school art foundations course by 1) conceiving of the classroom as an ecosystem, 2) welcoming the tension between contemporary curricular choices and the many traditional structures in his school, and 3) advocating for a classroom culture and class time to be focused on ideation, studious play, and ambiguous spaces to cultivate more authentic and meaningful art projects.