Greg Hollingshead grew up in Woodbridge, Ontario. He attended the University of Toronto Schools and the University of Toronto, graduating with a B.A. in English in 1968. His first book publication was in T.O. Now (House of Anansi, 1968), an anthology of young Toronto poets edited by Dennis Lee.

After travelling in Europe and North Africa, Greg returned to the University of Toronto to complete an M.A. in English. From 1970 to 1975 he lived in England--in London and Surrey--where he completed a Ph.D. at the University of London on George Berkeley, the eighteenth-century immaterialist.

Since 1976 Greg has published more than seventy stories and essays in magazines and anthologies in Canada, the U.S., and the U.K. His first book, Famous Players (Coach House), a story collection edited by Matt Cohen, appeared in 1982. His second and third books—the story collection White Buick (Oolichan) and the novel Spin Dry (Mosaic)—both appeared in 1992. (Spin Dry was reissued as a Harper Perennial paperback in 2006.) Greg's fourth book and third story collection, The Roaring Girl (Somerville House), edited by Patrick Crean, won the 1995 Governor General's Award for Fiction. The Roaring Girl was also published in England, the U.S., Germany, and China.

In 1998 Greg published his second novel, The Healer (A Phyllis Bruce Book/HarperCollins), the first book to appear under the HarperFlamingo imprint in Canada, England, and the U.S. together. The Healer was shortlisted for the 1998 Giller Prize, and in 1999 won the Rogers Writers' Trust Fiction Prize. The Healer and The Roaring Girl were reissued as Harper Perennial paperbacks in 2004. Also appearing in 2004 was Greg's third novel, Bedlam (A Phyllis Bruce Book/HarperCollins). Bedlam, a Globe 100 Book of the Year for 2004, was shortlisted for the regional Commonwealth Writers' Prize for Best Book, the Grant MacEwan Author's Award, the Georges Bugnet Award, and the Edmonton Book Prize and longlisted for the IMPAC Dublin Literary Award. In Canada, Bedlam was a Globe 100 Book of the Year and in the U.S., where it was published by St. Martin's (Thomas Dunne Books) in 2006, Bedlam was a New York Times Book Review Editor's Choice. In 2007 Greg was awarded the Lieutenant Governor of Alberta Gold Medal for Excellence in the Arts and in 2012 the Order of Canada and the Queen Elizabeth II Diamond Jubilee Medal. In 2011-12 he served as Chair of the Writers’ Union of Canada. Greg’s fourth story collection Act Normal (House of Anansi) was published in 2015 to excellent reviews. In 2016 he was awarded the Writers’ Guild of Alberta Golden Pen Award for Lifetime Achievement.

Professor emeritus at the University of Alberta and director of the Writing Studio at the Banff Centre, Greg lives in Toronto with his wife Rosa Spricer, a psychologist in private practice. They have one son, David.