Hip hop culture is typically excluded from conventional educational spaces within the U.S. Drawing on the experiences of an educator who works with urban high school students and university level pre- and in-service educators, this article examines the role of hip hop culture for student engagement in two settings--an alternative high school setting and the university classroom. The article explores how dialogue, as a core element of hip hop culture, is used in disrupting traditional vehicles of engagement, particularly between youth connected to hip hop culture and educators who are traditionally disconnected from the culture. Drawing upon dialogical pedagogy and analyzing an actual dialogue between urban youth and preservice teachers, the author examines the ways in which the student-researchers were "dissed" (disrespected) during and after the dialogue. Implications for practice and policy are explored. (Contains 1 note.)