This article describes a project in which undergraduate students of beginning drawing were brought together with free improvising musicians to explore interaction in collective real-time art-making. Following a series of guided rehearsals, the students were free to choose their own strategies for interactive group projects. We discuss these strategies based on video documentation as well as the students’ written reports and discussion comments. Overall, the students gradually shifted the emphasis of their work from temporally differentiated, imitative parallelisms between drawing and music toward more conversational and socially oriented strategies as well as more global strategies of representation employing common mental images. These findings are discussed with a view to future pedagogical work incorporating music with visual art, arguing that interactive contexts not only provide understanding of the temporal, processual, and social potential of visual art, but also hold a key to the students’ exploration of their own budding artistic autonomy.