This paper proposes the notion that early Native American autobiographical writings from such authors as William Apess provide rich sources for understanding syncretic authors and their engagement with dominant Anglo-Christian culture. Authors like William Apess construct an understanding of what constitutes Indianness in similar and different ways to the master narratives produced for Native peoples. By studying this nonfiction, critics can gain a broader understanding of contemporary Indian fiction like that of Sherman Alexie. The similarities and differences between the strategies of these two authors reveal entrenched stereotypes lasting centuries as well as instances of bold re-signification, a re-definition of Indianness. In analyzing these instances of re-signification, this paper focuses on the performance of re-membering, the controversy of assimilation/authenticity, accessing audience, the discourse of Indians as orphans, and journeys to the metropolis.