The Toronto-Dominion Centre, designed by Ludwig Mies Van Der Rohe: Planned, designed and built between the late 1950s and early ’60s, the T-D Centre was the architectural project that almost single-handedly brought Toronto into the Modern age. Though never popular with locals, it is admired around the world for its attention to detail and almost spiritual adherence to the logic of the grid. Sadly, it launched a wave of ghastly, second-rate International Style towers that blight this city and its suburbs to this day. Within a few short years, Modernism was shorthand for the cheap and the ugly. But in this case, Modernism achieved something akin to perfection. Unlike the vast majority of such towers; the T-D Centre succeeds at the level of detail as well as the big picture. Despite its Modernistist vocabulary, the towers — originally there were three — demonstrate Mies’s abiding interest in the formal qualities of classical architecture. His buildings don’t look like Greek temples, or even elicit the same response, but they express the same need for rationality and clarity. The one-storey banking pavilion at the southwest corner of King and Bay comes as close as anything Mies did to realizing his desire for an ideal structure, one oblivious to program, purpose and people.

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Sharp Centre for Design, Ontario College of Art and Design University, Will Alsop: When English architect Will Alsop came to town in the early years of the 21st century to design his now famous “Flying Tabletop,” he was an unknown quantity in Toronto. Though he had won the prestigious Stirling Prize for the Peckham Library in London, he had never done anything in North America. When the Sharp addition opened in 2004, it was greeted with loud criticism, especially by local architects, many of whom dismissed it as a sort of joke. Despite the outlandish appearance of a two-storey rectangle sitting atop 12 brightly-coloured and precariously angled steel columns, Alsop’s building solved a number of practical problems. Not only did it enable the school to stay open during construction, it opened up space beneath for a public square while creating a (still unmade) connection to Grange Park directly west. The pavilion also managed to express the spirit of experimentation and play that lies at the heart of an educational institution dedicated to art and design. Toronto, of course, had never seen anything remotely like it, and the sense of consternation was palpable. In the decade since then, however, Alsop’s wonderful structure has become a beacon of boldness, a reminder that architecture is a cultural as well as a mechanical activity, that it serves psychological as well as utilitarian purposes. Its effect has been a loosening up of architecture. It has liberated architects and audiences from the constraints of the conventional.

New City Hall, designed by Viljo Revell: When the competition to design Toronto’s newest city hall — the city’s fourth — was launched in 1958 by mayor Nathan Phillips, the result was outpouring of submissions: more than 500 from dozens of countries around the world. The process alone was enough to bring this dreary colonial backwater to international attention. When Finnish architect Viljo Revell was declared the winner in April, 1958, it was clear the decision was one that would radically alter Toronto’s image both within and without the city. Revell’s boldly curved towers — 20 and 27 storeys — seem to embrace the circular council chamber in the middle. Not surprisingly, the frankly futuristic aesthetic of the building, which was completed in 1965, shocked many Torontonians. Nearly half a century later it remains an iconic presence on the skyline. Although far from the tallest structure in Toronto, it manages to make its presence felt through the sheer power of its architecture. As boldly sculptural as any building in Toronto, it expresses the democratic impulse that lies at the heart of the city. Set well back from Queen St., it overlooks Nathan Phillips Square, Toronto’s only genuinely civic space, a place of celebration, commemoration and demonstration. Little wonder New City Hall has become the very symbol of Toronto. By any measure, it ranks among the most remarkable civic buildings in the world. Though it has not spawned any imitators, it has set the standard against which all other municipal buildings are judged. So far, it remains unsurpassed.

The Bay and Gable House, designed by numerous architects: This distinctive Toronto housing type can be seen across the older parts of the city — east and west end equally. Easily recognized in its mainly Gothic aesthetic, it features a sharply angled gable up top and a bay window running vertically, typically from the ground up to the roof. Its narrow width made it ideal for the compact urban form of 19th-century Toronto. Lots then were barely six metres wide, which meant that many such houses were tall — often three storeys — and semi-detached. The earliest remaining examples, dating from the 1870s, are said to be in Yorkville, but countless Bay ’n’ Gable houses can be found from Parliament St. in Cabbagetown west to Sherbourne St., the Annex, Little Italy, Trinity-Bellwoods and beyond. Its popularity dates from the last quarter of the 19th century, but even today it appears in modified form sometimes in suburban locations where it has been further adapted to incorporate garages. This supremely flexible building type says much about our predecessors’ love of practicality as well as their insistence on architectural beauty. These structures, though modest, were exquisitely decorated. They understood their role in the public realm and presented an unfailingly handsome face to the city. No surprise they are more popular than ever with 21st-century Torontonians who avidly seek out these houses.

D.T.A.H. Architects, formerly the Ontario Association of Architects, 50 Park Rd., designed by John C. Parkin: The first permanent headquarters of the OAA, this easy-to-miss, glass-and-brick box, opened in 1954 and was greeted as a harbinger of the new Toronto. Freshly returned from Harvard where he studied with Bauhaus master Walter Gropius, John C. Parkin (not to ne confused with John B. Parkin, with whom he worked), was hailed as a Modernist prophet come to save Toronto from its hopelessly outdated Victorian past. Though it’s hard now to feel the enthusiasm, and perhaps the discomfort, with which the city welcomed the structure, it was among the first signs that the 20th century had reached Hogtown. To 21st-century eyes, the building is an unremarkable brick box, small and somewhat dreary. Though larger than it looks, it is set too far back from the sidewalk to have much presence on the street. Indeed, chances are the vast majority of people who walk by never even notice it’s there. But such was the zeal for the new, and the apparent rationality of Modernism, that the building became a prototype for countless anonymous boxes, large and small, that line the streets of Toronto and countless other cities around the planet. Much has been written about the failure of Modernism, how it reduced cities to generic spaces hated by those who lived and worked in buildings that failed to acknowledge any living presence. Suddenly it became almost impossible to tell houses from offices from factories. Today, recognized as just another style among many, Modernism has been rehabilitated, and made safe for human habitation.