“Native American Surrealism” may be a contradiction in terms. If “surrealism” is a European creation, then joining it with “Native American” suggests an oxymoron. European surrealism was, however, based in part on Native expression. So “Native American Surrealism” could be used to identify an artistic mode avant la lettre appropriated by non-Natives. And some contemporary art by Native artists could be seen as a complex re-appropriation, a Native American surrealism après la lettre. This paper will examine the conjunction of “Native American” and “surrealism” and its significance by considering the work of five prominent Native artists from the Upper Midwest: Frank Bigbear, Julie Buffalohead, Star Wallowing Bull, Andrea Carlson, and Jim Denomie. To fully engage the issue of surrealism, the paper will also discuss their work in relation to other aspects of contemporary art, including the revival of interest in narrative, post-Pop representational styles, and the current fascination with satire.