This chapter examines the life and writings of Don Asher, who studied with pianist Jaki Byard before embarking on a career as a New England society band and honkytonk pianist and later as a nightclub pianist in San Francisco, including a long stint at the famed hungry i. Asher was also a novelist, short-story writer, essayist, and collaborator, and analysis of selected works of his fiction and nonfiction uncovers his enduring and sometimes transgressive fascination with African American music and culture. While Asher’s work appears to illustrate “the problem with white hipness” (Ingrid Monson) or “love and theft” (Eric Lott), his ethnic satire was aimed not only at African Americans but also at other groups—Italians, Irish, Jews—as well as at himself and his fictional counterparts. This chapter considers the rich stew of literary and performance traditions in which Asher found models for his satirical, comedic impulses.