At the age of 14, after seeing the film Young Man with a Horn (in which Kirk Douglas plays a character modelled on American jazz cornetist Bix Beiderbecke), Masekela took up playing the trumpet.
Vid 14 års ålder, efter att ha sett filmen Young Man with a Horn (där Kirk Douglas gestaltar den amerikanske trumpetaren Bix Beiderbecke), började han spela trumpet.