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Born in Kampala to Abdullah Mukwaya a Ugandan teacher and religious leader and Mariam Aziidah a beautician, Usama joined filming in 2010 with Mariam Ndagire Film and Performing Arts Center where he finished with his first film Hello (2011). A year later after finishing his networking diploma at Makerere University, he attended the 7th Maisha Film Lab founded by Mira Nair where he worked on his second short She Likes Prada (2012).