Toronto has had a reputation of always being the bridesmaid and never the bride when it comes to its portrayal in the movies. As a stand-in for large American cities, it has fueled a busy film-production industry but done little to attract the curious since its streets and skyline always depict some other place. That is still the case overall, but the city claimed a starring role in Atom Egoyan's well-received film Chloe (2009). Toronto was itself, for once, and plays a key role.
As a city on the page, however, Toronto can claim a rich legacy. It's home to many of the country's most prolific and acclaimed writers, which might be the reason for its literary stardom.
Margaret Atwood's The Robber Bride (Emblem Editions) pays homage to Toronto with a story that covers three decades of life in the city. Some of her other novels -- The Edible Woman, Cat's Eye, and The Blind Assassin (all published by Emblem Editions) -- also use Toronto as a backdrop. In the Skin of a Lion, by Michael Ondaatje, the celebrated author of The English Patient (both published by Knopf Canada), is a moving love story that brings the city's landmarks to life. Carol Shields, who died in 2003, set her final novel, Unless (Harper Perennial), in Toronto's streets. Michael Redhill's Consolation (Doubleday, Canada) bounces back and forth between contemporary Toronto and the city in the 19th century.
Another notable novel is Cabbagetown, by Hugh Garner, the story of the fight to survive in a Toronto slum in the 1930s. (Cabbagetown was famous as the largest Anglo-Saxon slum in North America.)
Cabbagetown -- "A few houses on almost every street were as verminous and tumbledown as any in the city, but next door or across the street was the same type of house, clean and in good repair, reflecting the decency or pride of the occupants, or reflecting the fact that the tenant was buying it. In 1929, most Cabbagetowners rented their homes, from the ingrained habit of generations or because they refused to tie themselves down to the district. This was a neighborhood almost without tenements, and the streets were lined with single-family houses, many of whose upper stories accommodated a second family.
The citizens of Cabbagetown believed in God, the Royal Family, the Conservative Party, and private enterprise. They were suspicious and a little condescending towards all heathen religions, higher education, 'foreigners,' and social reformers. They were generally unskilled working people, among whom were scattered, like raisins in a ten-cent cake, representatives of the State -- such as postmen, civic employees, streetcar conductors, and even a policeman or two."
-- From Cabbagetown, by Hugh Garner, 1950
For those more interested in possible futures than the past, there's an Afro-futurist/sci-fi novel called Brown Girl in the Ring, by Nalo Hopkinson (Warner Books). Some other books to consider: Noise (Porcupine's Quill) and How Insensitive (Doubleday Canada), by Russell Smith; Headhunter, by Timothy Findley (HarperCollins Canada); Then Again, by Elyse Friedman (Random House Canada); Lost Girls, by Andrew Pyper (Harper Collins Canada); and The Origin of Waves, by Austin Clarke (McClelland & Stewart). Clarke has also written three novels that are collectively known as the Toronto Trilogy: The Meeting Point, Storm of Fortune, and The Bigger Light (all published by Knopf Canada). The literary legend Robertson Davies was working on the third novel in his own Toronto Trilogy when he died in 1995. The first two books, Murther and Walking Spirits and The Cunning Man (both published by Penguin Books), were published in 1991 and 1994, respectively.
If you like the look of Old City Hall, pick up the novel Old City Hall, by Robert Rotenberg (Picador). Published in 2009, the story -- written by a veteran criminal lawyer -- explores Toronto's noir side.
Insightful books on architecture include Emerald City: Toronto Revisited, by John Bentley Mays (Viking), and as handy reference to recent buildings, A Guidebook to Contemporary Architecture in Toronto, by Margaret and Phil Goodfellow (Douglas & McIntyre), covers the bases.