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Brandon nasceu em Detroit, Michigan, filho do bispo Wayne T. Jackson, pregador do Great Faith Ministries International. Jackson estudou no West Bloomfield High School. Após a formatura, Ele se mudou para Los Angeles para ser comediante. Ele alega ter sido "descoberto" no Laugh Factory. O seu papel como "Junior" no filme "Roll Bounce" fez ele ganhar o Black Reel Award 2006 por Performance estreiante. Em 2006, Jackson foi o anfitriã do "Up Close and Personal Tour", junto com Chris Brown, Ne-Yo, Lil Wayne, Juelz Santana e Dem Franchize Boyz. Ele estrelou no show "Wild 'N Out", com Nick Cannon, e também "Trovão Tropical" como Al Pacino. Brandon se encontra filmando a adaptação da série de livros Percy Jackson e os Olimpianos, como Grover Underwood, da qual o primeiro filme estreiou em fevereiro de 2010.
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