[7] McDonald was born in Kingston, Ontario,[2][8] and later moved to Toronto, where he graduated from film school at Ryerson University.

[8] His feature-length directorial debut, Roadkill, won the award for Best Canadian Film at the Toronto International Film Festival and McDonald earned some notoriety and media attention when he quipped, while accepting his $25,000 prize from TIFF for Roadkill, that he planned to spend the money on "a big chunk of hash".

[10][11][12] Roadkill was the first of a trilogy of road movies—including Highway 61 (1991) and Hard Core Logo (1996)—the film launched his reputation as a maverick independent.

[8] In 1996, Hard Core Logo won the award for Best Canadian Feature at Sudbury's Cinefest and at the Vancouver International Film Festival, marking his second win at the latter.

[8] Hard Core Logo has been frequently ranked amongst the greatest movies ever to come out of Canada,[7] and is considered to be McDonald's breakthrough film.

McDonald, along with six other directors, shot 20 short films about Toronto musicians and the places where their musical lives were transformed.

[20] However, work on the film remained dormant until McDonald and screenwriter Daniel MacIvor decided to rewrite their original screenplay to be about two women instead; these roles were ultimately played by Tracy Wright and Molly Parker.

[22] Hard Core Logo 2 premiered at the Whistler Film Festival on December 4, 2010, with the members of Die Mannequin and McDonald walking the red carpet.

This caused the film to receive mixed reviews; Postmedia News wrote that it is a film about "artistic inspiration, maintaining a pure creative heart and connecting with others through honest expression"[24] while The Globe and Mail referred to the feature as giving the audience "no sense of urgency, desire, or necessity" to continue watching.