This article explores how conceptions of choice and visions of the future are constructed within the context of specialized arts programs in two Canadian public high schools. The authors consider how discourses of the arts are implicated in the way that possible futures are envisioned differently, delimiting the range of choices available to students. Their analysis shows how choices are unequally distributed and possible futures unequally constructed in ways that reinforce social class hierarchies. The discussion of the data is organized around the contrast in how three tropes—"the architect," "the fifth year," and "being lazy"—emerge in both school contexts in relationship to students’ futures. By illustrating how the arts operate in this process, the authors challenge the common assumption that arts programs have the inherent ability to transcend social structures in general and social class processes in particular. The authors conclude by considering the implications of their analysis for how notions of choice are understood in relationship to specialized arts programs.