He formed the band Chiskop together with three childhood friends, upon his release from Diepkloof Prison. He had been imprisoned at the age of 16 for car theft. His first solo effort, "9II5 Zola South", became 1999's top-seller, and he was nominated as "Best Newcomer" at the 2000 South African Music Awards (SAMA's). The following year's "Nkalakatha" album title track was a hugely successful hit with black as well as white listeners, earning him the "Song Of The Year" award at the 2001 SAMA's. Mandoza sang in several of South Africa's many languages, including English, Afrikaans, Zulu, and Xhosa, giving him wide appeal with South African listeners.