Born in London, Bailey grew up in England and Barbados before migrating to Canada. Before taking up his current position at TIFF, he was a Festival programmer for eleven years, heading its Perspective Canada programme and founding its Planet Africa section.
For many years, Bailey was a writer and broadcaster on film. He reviewed for Toronto’s NOW Magazine, CBC Radio One and CTV’s Canada AM. He presented international cinema nightly on Showcase Television’s national programme The Showcase Revue, and produced and hosted the interview programme Filmmaker on the Independent Film Channel Canada. He has been published in The Globe and Mail, The Village Voice, CineAction!, and Screen, among others.
Bailey has curated film series for Cinematheque Ontario, the National Gallery of Canada, the National Film Board of Canada, and Australia’s Sydney International Film Festival. He has also served on awards juries in Canada and internationally, including in China, the U.S., Turkey, Greece, South Korea, Burkina Faso and Tanzania, and has been a guest speaker at several Canadian universities, the Smithsonian Institution, Harvard University and the Banff Centre for the Arts.
Bailey currently sits on the Advisory Council for Western University’s School for Arts and Humanities and for Haiti’s Cine Institute film school. He is also a board member of Tourism Toronto, and he teaches a course in programming and curation at the University of Toronto. Bailey was on the Toronto 2016 NBA All-Star Steering Committee, and was the co-chair of the Arts & Culture Working Group of Toronto’s CivicAction. He is a former board member of the Ontario Film Development Corporation, and served on the Advisory Board of the Royal Ontario Museum’s Institute for Contemporary Culture. In 2007, Bailey was a part of the delegation accompanying Canada’s Governor-General Michaëlle Jean on her state visit to Brazil.