Hugh Ramopolo Masekela was born on April 4, 1939, in Witbank, South Africa. He began singing and playing piano as a child. But at age 14, after seeing the film, YOUNG MAN WITH A HORN, where Kirk Douglas portrays American Jazz trumpeter, Bix Beiderbecke, he took up trumpet, given to the young Hugh by Archbishop Trevor Huddleston, the anti-apartheid chaplain at St. Peters Secondary School.
Masekela had been greatly moved by the music he heard on the 78 RPM gramophone records of Louis Armstrong, Jelly Roll Morton, Bessie Smith, Ma Rainey, Chick Webb, Ella Fitzgerald, Sy Oliver, Duke Ellington, Count Basie, Coleman Hawkins, Cab Calloway, Fats Waller, Sarah Vaughan, Louis Jordan, The Ink Spots, the Mills Brothers, Billie Holiday and Charlie Christian.
In his teens, he fell in love with Dizzy Gillespie, George Shearing, Miles Davis, Clifford Brown, John Coltrane, Cannonball Adderley, Horace Silver, Art Blakey, Lee Morgan, Kenny Dorham, Oscar Peterson, Bud Shank, Dave Brubeck, Paul Desmond, Stan Getz, Jackie & Roy Kral, June Christy Shorty Rogers, Gerry Mulligan, Chet Baker, Bud Powell and Mahalia Jackson.