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Huddleston asked the leader of the then Johannesburg "Native" Municipal Brass Band, Uncle Sauda, to teach Masekela the rudiments of trumpet playing. Masekela quickly mastered the instrument. Soon, some of his schoolmates also became interested in playing instruments, leading to the formation of the Huddleston Jazz Band, South Africa's first youth orchestra. By 1956, after leading other ensembles, Masekela joined Alfred Herbert 's African Jazz Revue.

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Masekela traveled throughout Africa in the 1970s, becoming involved in the continent’s varieties of music, teaching for a year in Guinea, playing in the band of popular Nigerian performer Fela Ransome-Kuti, recording five albums, and touring with the highlife band Hedzoleh Soundz. In the 1980s, after starring in outdoor concerts in Lesotho and Botswana that drew throngs of both black and white South Africans, he settled in Botswana and set up a mobile recording studio near the South African border in order to record that country’s musicians. He also played on Paul Simon ’s “Graceland” world tour. In 1990 he received a telephone call from his sister Barbara, in Johannesburg , reporting that the South African government had declared amnesty for political exiles; herself an exile, she had returned home to become Nelson Mandela ’s chief of staff.


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