Oakwood Collegiate Institute

• Rosalie Abella - Appointed to the Supreme Court of Canada. • Gil Adamson - Author of The Outlander, which won the Books in Canada First Novel Award in 2008. • Jeremy Adelman - Professor of History at Princeton University. • John Arnup - Judge on the Court of Appeal for Ontario who pioneered universal legal aid in Ontario. • Harry Arthurs - Former Dean of Osgoode Hall Law School and President of York University. • Michael Baker - Physician, academic, and cancer researcher. • Micah Barnes - Singer-songwriter with the bands Loudboy and The Nylons. • Alan Bernstein - Cancer researcher. • Jully Black - Juno Award-winning R&B singer-songwriter. • Gil Boa - Sport shooter who competed in the 1952 Summer Olympics, 1956 Summer Olympics, 1960 Summer Olympics, 1964 Summer Olympics, and 1972 Summer Olympics. • Mark Breslin - Entrepreneur, stand-up comedian and actor; co-founded Yuk Yuk's, the largest chain of comedy clubs in Canada. • Harry Bruce - writer and journalist. • Jane Bunnett - Juno Award-winning saxophonist, flautist, and bandleader known for her Afro-Cuban jazz melodies. • Torquil Campbell - Singer and songwriter for the Montreal-based indie rock band “Stars”. • Brendan Canning - Founding member of the band "Broken Social Scene". • Elinor Caplan - Businesswoman and politician. • Ann Y. K. Choi - author and educator. • Jerry Ciccoritti - Gemini Award-winning film director. • Alfred Henry Clarke - Member of Parliament. • Kamari Maxine Clarke - Professor. • Norman Clarke - Olympian. • Gerald Clawson - Swimmer at 1936 Summer Olympics. • Carl Cole - Co-founder of Coles Bookstore, once the largest bookstore chain in Canada. • Evan Cranley - Musician with the bands Stars and Broken Social Scene. • Dianne Cunningham - Progressive Conservative member of the Legislative Assembly of Ontario from 1988 to 2003, and cabinet minister in the governments of Mike Harris and Ernie Eves. • Wes Cutler - Football player in the Canadian Football League for six seasons for the Toronto Argonauts. • Arthur P. Dempster, Professor Emeritus in the Harvard University Department of Statistics. • DijahSB, musician. • Charles Dinsmore - Football player for the Toronto Argonauts and NHL hockey player on the Montreal Maroons in the 1920s. • Laverna Katie Dollimore - Awarded the Order of Canada for her participation in the Canadian Caper, in which Canadians orchestrated the release of Americans in Iran in 1979. • Bill Domm - Member of Parliament from 1979 to 1993; known for his crusades against the metric system and his support of capital punishment. • Hannah and Vivien Endicott-Douglas - Actresses and sisters. • Bernard Etkin - University dean; expert in aircraft guidance and control • Bob Ezrin - Music producer and keyboardist, best known for his work with Lou Reed, Alice Cooper, Kiss, Pink Floyd, Peter Gabriel, and Phish. • Charlotte Fielden - Novelist, playwright, actress and poet. • Greg Francis - Olympic basketball player and coach. • John Fraser - Journalist, writer and academic. He served as Master of Massey College in the University of Toronto. • David French - Poet and playwright. • John Judah Glass - Represented St. Andrew in the Legislative Assembly of Ontario from 1934 to 1943 as a Liberal member. • Dan Goldstick, Philosopher, writer and political activist; Professor Emeritus at the University of Toronto. • K.M. Graham - artist. • Kadre Gray, professional basketball player. • Francess Halpenny - Dean of the Faculty of Library Science at the University of Toronto from 1972 to 1978, now known as University of Toronto Faculty of Information. From 1969 to 1988, she was one of the editors of the Dictionary of Canadian Biography. • James Milton Ham - Engineer, university administrator and 10th President of the University of Toronto. • Lucas Hammond, Olympian. • Sharon Trostin Hampson - Member of the children's musical trio Sharon, Lois & Bram. • Bill Hanley - Member of Hockey Hall of Fame as a builder. • G. Arnold Hart, president, chairman, and chief executive officer of Bank of Montreal. Member of Order of Canada. • Alan Milliken Heisey Sr. - Activist, author, publisher and politician. • Lionel Hitchman - Played twelve seasons in the National Hockey League for the Ottawa Senators and Boston Bruins, where he was team captain. • Mark Jones - Sportscaster. • Paul Jones - Toronto Raptors' radio play-by-play announcer on Fan 590. • Isaiah L. Kenen - Journalist, lawyer and philanthropist • Murray Koffler - Pharmacist, businessman, and philanthropist; best known for creating the Canadian pharmacy retailer Shoppers Drug Mart. • James Laxer - Political economist, professor and author. • Stephen Lewis - Politician, broadcaster and diplomat. Leader of the Ontario New Democratic Party for most of the 1970s. • Aaron Long - Animator, director of Bojack Horseman • John B. Macdonald - President of the University of British Columbia from 1962 to 1967. • Jama Mahlalela - Assistant coach for the Toronto Raptors of the National Basketball Association. • Larry D. Mann - actor. • Harry Mannis - Broadcaster. • James Harley Marsh - Editor, writer and encyclopedist of The Canadian Encyclopedia. • Goldwyn Arthur Martin - Judge of the Court of Appeal for Ontario and one of the most prominent experts in criminal law in Canada. • Malcolm Wallace McCutcheon - Lawyer, actuary and politician. • George McGill - Royal Canadian Air Force officer who participated in The Great Escape. • John McKennell - Hockey coach. • Mary di Michele - Poet and author. • Frank Miller - 19th Premier of Ontario. • Boonaa Mohammed - Spoken-word poet and writer of Oromo descent. • MorMor, musician. • Emilie Mover - Juno Award-winning singer-songwriter. • Winifred Needler - Egyptologist. • Jean Newman - Toronto politician who served as Controller budget chief and was the first woman to run for Mayor of Toronto. • E. Herbert Norman - Diplomat and historian. • Seth Nyquist - musician. • Kardinal Offishall, Rapper. • Paolo Pietropaolo - Journalist, broadcaster, composer and writer. His CBC series The Wire won a Peabody Award. • Peter Li Preti - Toronto city councillor. • Joshua Primo, professional basketball player. • James Randi - Stage magician and scientific skeptic best known for his challenges to paranormal claims and pseudoscience. • Paul Hartley Raney - Second Lieutenant fighter pilot with the Royal Flying Corps, 66th Squadron. Shot down and killed in World War I. • Harry Rasky, Documentary film producer. • Escott Reid - Diplomat. • Ivan Reitman - Film producer and director. • John Roberts - Oxford PhD elected (and defeated) three times to Canada's House of Commons. • Charles Gordon Roland - Author, editor, and professor of the history of medicine. • Tony Rosato - Actor and cast member on Saturday Night Live during the 1981–82 season. • Larry Rosen - Chairman and CEO of Harry Rosen Inc. • Devyani Saltzman - Author, curator and journalist; daughter of film directors Paul Saltzman and Deepa Mehta. • Robert Hood Saunders - Mayor of Toronto, President of Canadian National Exhibition, chairman Ontario Hydro. • Robin Sears - Former broadcaster at CITY-TV. Now a communications, marketing and public affairs adviser. • Louis Shannon - Toronto politician who served for many years on Toronto City Council and the Toronto Board of Control. • James Shaw - Founder and lead guitarist of indie rock band Metric, and founder of the band Broken Social Scene. • Andrew Simone - Physician, dermatologist and co-founder of Canadian Food for Children. • Doris Slater - cartoonist, painter, and art teacher. • Art Smith - Played on Oakwood's 1923-24 OHA-Junior hockey team. Went on to play for the Toronto Canoe Club, Toronto Falcons, Toronto Maple Leafs, Ottawa Senators, Boston Cubs, and Chicago Shamrocks. • Jason Sniderman - Musician and businessman. • Warren Snyder - Olympian and doctor. • Reginald Stackhouse - Member of the Canadian House of Commons. • Sinclair Stevens, Lawyer, businessman and cabinet minister. • Betty Tancock - Swimmer who competed in the 1932 Summer Olympics in Los Angeles. • Andy Thompson - Leader of the Ontario Liberal Party and later served as a Senator. He was elected as the Member of Provincial Parliament for the west-end Toronto Dovercourt electoral district in 1959. • Eddie Thompson - Award-winning, all-star and Grey Cup champion halfback in the Ontario Rugby Football Union. Thompson was a war hero who lost his life in World War II. • Michael Tulloch - The first Black judge appointed to the Ontario Court of Appeal. • Adam Vaughan - Radio and TV journalist; Member of the Canadian House of Commons. • Patrick Watson - Broadcaster, television and radio interviewer and host, author, commentator, television writer, producer, and director. • Al Waxman - Actor and director of over 1000 productions on radio, television, film, and stage; best known for his starring roles in the television series King of Kensington and Cagney & Lacey. • Ernest Weinrib - Law professor. • Witch Prophet - Musician. • York Wilson - Painter and muralist.