"Rideables" are a series of electronically-powered performative sculptures that serve as a platform for dialogue and interactions with and across diverse groups of the Santa Cruz community. This series provides insight to the variable possibilities of collaboration among and between otherwise dissociated groups. Confronted with social barriers surrounding underrepresented communities, "Rideables" serve as a developing collaborative art practice that asks participants and viewers to embrace diversity and create radical dialogue through joyous, and fun interactions. This thesis explores the history and future of this work in order to address social dissociation. It also proposes a framework for collaborative art making, object oriented sculpture, and community engagement. Analyzing the making, documentation, enactment, and exhibition of these sculptures in a written format is an attempt to demonstrate an understanding of the work in a broader context and to provide scholarly dialogue around the social implications of these works.