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Bob Hope once joked that Toronto would be a nice place – when it was finished. That was more than three decades ago, during the building boom that would define the city's skyline by its gold and marble bank headquarters and its rude and record-shattering CN Tower. It wasn't exactly pretty, but at least the development spurt suggested a city on its way up.

Today, Toronto is as unfinished as ever. It is the Western Hemisphere city with the most tall buildings under construction. But unlike the city Mr. Hope visited, the cranes are reserved for upscale condo projects instead of office buildings. By 2015, Toronto's skyline will sport 44 towers exceeding 150 metres in height, up from only 13 in 2005, according to the Chicago-based Council on Tall Buildings and Urban Habitat. Clearly, modern Toronto has a height obsession.

Indeed, theatre impresario David Mirvish wants to outdo them all by enlisting the revered Toronto-born architect Frank Gehry to design three luxury condo towers – totalling more than 250 storeys – for a patch of King Street West that Mr. Mirvish's father once revitalized with his theatres. Everyone from Conrad Black to Toronto Star architecture critic Christopher Hume seems gaga at the prospect of not one, but three Gehry mega-towers gracing the architect's hometown.

The problem with all these fancy skyscrapers, from the Trump Tower and Daniel Libeskind's L-Tower to the undulating balconies of the now-rising One Bloor, is that they represent the lipstick-on-a-pig approach to urban development. At best, these exclusive downtown condos with their "money shot" views are simply turning Toronto into Hogtown with gaudy sequins.

"This is not a good-looking city," the straight-talking celebrity chef Anthony Bourdain said on a 2012 visit to Toronto. "Your English-Presbyterian past has not served you well architecturally."

The Los Angeles-based Mr. Gehry turned the screws last month. While in town to defend his project and the proposed demolition of the existing Edwardian-era warehouses on the site, he told the Toronto and East York Community Council that Toronto had only two buildings worth preserving – Old City Hall and Osgoode Hall. The truth hurts.

Montreal has its share of urban eyesores – most of them built during the Jean Drapeau era of the 1960s and 1970s – but the city's glorious past and collective aesthetic have left it with an architectural ambience that Toronto can only envy. Recently, Montreal has excelled at small-scale urban renewal and beautification projects that showcase the city's charm and sense of proportion.

Toronto has achieved far less with far greater means. The streetscapes of rich Toronto are still dominated by shoddy shacks and tacky storefronts. Looking up along most downtown streets – including Yonge, Queen and other prime retail arteries – you notice the disrepair of so many buildings. Most city councils wouldn't tolerate such neglect, but Toronto's seems too busy reviewing the next towering condo project to care.

No matter that they go up with almost total disregard for their surroundings, we're told these skyscrapers provide the density and gentrification that make for a vibrant downtown. But several low-rise buildings side-by-side can deliver the same density as a single 80-storey tower that requires a wide empty zone at its base and, usually in Toronto, has a vacant lot beside it.

"Tall buildings will, by their very geometry and scale, always struggle to relate to the spaces that a city needs in order to work successfully," Prince Charles noted more than a decade ago in bemoaning London's skyscraper boom. "They cast long shadows; they darken streets and suck life from them; they tend to violate the sense of public space so vital to a living street, either by requiring a plaza to give them light, or by refusing to align with existing buildings, because of the difficulties of entering and servicing them without a large and cluttered forecourt."

As New York Times architecture critic Michael Kimmelman recently asked about his city's tall condo boom: "What do these projects add at street level where the other 99 per cent live? What's their return for claiming the skyline that is our collective identity?"

Mr. Mirvish has shown his sensitivity to such questions and Mr. Gehry has a track record that merits the benefit of the doubt. Still, what Mr. Mirvish calls a "sculpture" is just a condo project. Without a broader effort to fix up Toronto's ugly streets, it's still just lipstick on a pig.

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