This article describes "Youthscapes," a year-round afterschool program in the San Francisco East Bay Area (CA) that offers urban youth the opportunity to use technology to reconstruct their identities in at least two ways: (1) by encouraging its apprentices to create media content that directly counteracted stereotypes about urban youth; and (2) by creating group cohesiveness within the apprentice program, which also facilitated meaningful interactions with members of various communities. The program encouraged its participants to create alternative "families" that provided them with a safe haven where they could explore their identity against the backdrop of adults' generally negative images. This empowered urban youth of color to engage actively in reclaiming the representations of their experiences, both in the adult-controlled landscape of their media worlds and on their streets.