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This qualitative case study investigates how creating musical albums functions as a transformative assessment for 14 in-service music educators in a graduate Hip-Hop pedagogy course. Drawing on Culturally Sustaining Pedagogy and Self-Determination Theory, we analyze how educators use artistic creation to articulate evolving professional identities and critique societal inequities. Findings indicate that album creation is a powerful assessment tool that fosters critical consciousness. The process supports educators' autonomy, competence, and relatedness, catalyzing profound identity augmentation. This work validates Hip-Hop as a rigorous pedagogy and offers a model for arts-based teacher education that is authentic, culturally sustaining, and liberatory, honoring the legacy that made the work possible.