The article explores the connections between the seemingly dissimilar experiences of teaching required courses in Renaissance literature and literature by historically underrepresented authors. Both fields feature unfamiliar and challenging histories and texts. Moreover, the requirement itself, though necessary, is a constraint on autonomy that many students resent, which can impede their motivation to learn. Using research on intrinsic motivation and autonomy, we argue for giving students more opportunities to determine their own readings, assignments, and syllabi within these required classes.