This article documents work with pre/in service teachers who are university students across three universities in three regions of the US, across multiple courses. Given our shared concern about the narrowing of space for imaginative literacy practices in schools, we focus on our collective use of open-ended, arts-based pedagogies as a way to challenge how we, as instructors, and our students conceive of literacy practices. A collection of Shaun Tan texts (including picturebooks, wordless graphic novels, and other multimodal/media texts for young people) served as focus texts across our three classroom contexts. We found surprise, a problematizing of narrow literacy definitions, and flexibility were all common ways of responding to this open-ended, arts-based literacy work. It resulted in tensions around and challenges of conventional or ordinary classroom literacy practices and pedagogical choices.