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Wayang Hip Hop is a group led by dalang Ki Catur “Benyek” Kuncoro that combines Javanese wayang kulit conventions and hip hop music. This article traces the history of the group in relation to key developments in wayang kontemporer, while exploring controversies in its reception. Wayang Hip Hop is analyzed as an important new version of wayang that has garnered substantial attention from young spectators. Five reasons for the appeal of the performance are identified: (1) its complex musical intersections, (2) the radical adaptation of classical wayang stories to address contemporary problems, (3) the extension of the conventions of the gara-gara comic interlude into a full performance, (4) the adaption of Javanese wisdom to new settings, and (5) the adaptability of the production, which can has been presented in very diverse contexts.