A former art teacher and cartoonist, Gillies MacKinnon became intrigued with film and started experimenting with the medium. His work won him acceptance into the National Film School, where he first met future collaborator Shane Connaughton. "Passing Glory" (1986), his graduation film, also marked his first collaboration with his brother Billy, who served as producer. MacKinnon's first film given any wide release was "Conquest of the South Pole", a 1989 docudrama about unemployed Edinburgh youths who attempt to recreate Roald Amundsen's expedition to the South Pole. He followed this with two BBC telefilms, "Needle" (1990) and "The Grass Arena" (1991). The latter, based on the true story of an alcoholic ex-boxer who finds redemption as a chess champion, won MacKinnon the prestigious Michael Powell Award at the 1991 Edinburgh Film Festival.