This essay describes a set of unconventional performances that I codirected with cultural historian John Sienicki. It demonstrates how we mixed genres, combining vocal music with related theatrical scenes, novels, and lectures; how historical research and musical praxis intersected in our creative process; how our improvisational rehearsal style worked; and how we designed performances with performers and intended audiences in mind. Some specific topics discussed are Schubert’s songs for female characters; the Vienna Volkstheater and its music; Lieder duets; and links between Schubert and the German historical-fiction writer Benedikte Naubert. These shows grew out of historical research and sometimes led to new research projects. I argue for the value of teaching Lieder performance by bringing in awareness of the songs’ historical and literary contexts. As some songs crossed genre boundaries, the worlds of theatrical music and art song can blend. Lieder existed in a complex, interconnected world, and nonstandard performances can accentuate their beauty and illuminate their meaning.