[1] McGregor grew up in the then Transkei (now part of the Eastern Cape Province),[2] where his father was headmaster at a Church of Scotland mission institution called Blythswood.
Dargie mentions the following as examples of this complexity which might be seen to have influenced McGregor in his own music, both as composer/arranger and as band leader: "...a great number of style characteristics are to be found: relating not only to harmony and scale, but to melody, structure and phrasing, form, rhythm, instrumentation, singing techniques, and so on.
"[1] After school and a stint in the merchant navy training academy The General Botha at Gordon's Bay in the Western Cape in 1952–53, McGregor enrolled at the South African College of Music, then headed by Professor Eric Chisholm.
[citation needed] Here McGregor was exposed to a different set of influences, during the day Béla Bartók and Arnold Schoenberg, and at night recordings of Duke Ellington and Thelonious Monk, and the live music of local jazz musicians such as Dollar Brand (now Abdullah Ibrahim), Cecil Barnard (now Hotep Idris Galeta), Christopher Columbus Ngcukana, Vincent Kolbe, "Cup-and-Saucers" Nkanuka, Monty Weber, the Schilder brothers, and many others who were active in the vibrant Cape jazz scene at that time, the mid-1950s.
This group consisted of Mzimkulu "Danayi" Dlova on alto, Chris Ngcukana on baritone, Ronnie Beer on tenor, Willie Netie on trombone, Sammy Maritz on bass and Monty Weber on drums.
The Blue Notes at this stage consisted of Mongezi Velelo (and later Sammy Maritz) on bass, Early Mabuza on drums, Dudu Pukwana on alto and Nikele Moyake on tenor.
McGregor is perhaps best known for his foundation and leadership of The Blue Notes, a South African sextet that included collaborators Dudu Pukwana, Nikele Moyake, Louis Moholo, Johnny Dyani and Mongezi Feza.