This paper presents a broad-reaching effort to interrogate enduring colonial legacies as experienced by Native American youth in the United States of America and Black Portuguese youth of Cape Verdean origin in Portugal. As part of its methodological approach, it uses hip-hop--a cultural movement composed of four elements including rap music--to examine how youth from specific communities access knowledge which is denied to them in schools, give revolutionary voice to their realities, and broadcast perspectives on race, place and belonging. When knowledge is negated in learning institutions, non-formal education created by youth is a powerful force in re-affirming tradition and transformation. Hip-hop becomes a medium to create alternative educational projects addressing the needs of youth in San Francisco, USA, and Lisbon, Portugal, where this research was conducted.