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Pumpkinhead is an underground rapper with numerous affiliations, including producer Marco Polo, with whom he collaborated for the acclaimed full-length album Orange Moon Over Brooklyn (2005). Born Robert Alan Diaz in Brooklyn, NY, on September 17, 1975, Pumpkinhead made his solo recording debut in the late '90s on the Brooklyn-based independent label Makin' Records with a pair of 12" releases: Dynamic (1997) and Dynamic (Remix) (1998). A few years later on Makin' Records he made his full-length solo album debut with The Old Testament (2001). During this same time period around the turn of the century, Pumpkinhead was affiliated with the groups Brooklyn Academy, O.B.S., and Skeme Team, among others, and was featured on several releases, most notably the Brooklyn Academy compilation The Academy Awards — A Greatest Hits Collection, Vol. 1: The Classics (2003). In 2002 Pumpkinhead released the seven-track mini-album Beautiful Mind on the label Third Earth Music, followed a few years later by Orange Moon Over Brooklyn, an acclaimed collaboration with producer Marco Polo released on Soulspazm Records. In 2004 he founded the label Red Army Inc., on which he released numerous mix albums in the years that followed. Moreover, a full-length album collaboration with Brooklyn Academy, Bored of Education (2008), was released on the label Gold Dust Media.