Bra Hugh was born in KwaGuqa township in Witbank and began singing and playing the piano as a child.
After seeing the film Young Man with a Horn when he was 14, Masekela began playing the trumpet. His first trumpet was given to him by Archbishop Trevor Huddleston, an anti-apartheid chaplain at St. Peter’s Secondary School.
He soon mastered the instrument and by 1956 joined Alfred Herbet’s African Jazz Revue. Bra Hugh’s music was inspired by the turmoil that South Africa went through during apartheid and he said it was used as a weapon to spread political change.