We show how coauthor, Delainia Haug, and her students use Web 2.0 technologies in educational and empowering ways. We offer an account of Delainia's purposes for her curriculum, along with units of study and students' responses to this curriculum. We argue that the curriculum, which focused on media analysis and production, engaged students--many of whom had no access to computers outside school--because it paired digital tools with intellectual challenge, hard work, interactions with community members, and a space for students to represent their identities and demonstrate competence. Initial findings from the study suggest that rigor and engagement in this urban English classroom were inextricably tied to a curriculum that actively involved students in the production of knowledge through complex literacy tasks and invited emotional investment and immersion, rather than analytic distance, in relationship to texts.