Ever since graphic designer Milton Glaser created the I [heart] NY slogan in the seventies—helping to bring New York City back from the edges of bankruptcy—the idea of “place branding” has captured municipal imaginations the world over. But does creating a new image for a city really make a difference? We picked five brands and put them through their paces:

Brand London: City of Possibility
In 2003, Global branding agency Interbrand came up with this logo, which may have helped with the European capital’s recent selection as the 2012 Summer Olympics site. It has a nice ring to it, and for an international city like London, it doesn’t over-promise. But the powers-that-be may be trying to make this brand work a little too hard. A recent news report says the campaign will be used not just to hype London’s Olympics coup but to allay fears caused by last summer’s subway bombings and change perceptions about the city as a place of fog and bowler hats. All this in an ad campaign? The city may be unlimited, but a brand identity is not. —B+

Brand Toronto: City of a Little Less Possibility
When this brand was unveiled this past June, the press release called Toronto “a city of imagination” that “embraces individuality.” Imagination? Individuality? It can’t even come up with its own logo! The weird blue teardrop on the left is meant to represent the letters T and O, merged in what the website calls a “fluid and energetic form.” Sure. Maybe if you look a little harder, you’ll see the figure $4,000,000—the amount Toronto taxpayers shelled out for this recycled version of London’s brand. —F

Brand Montreal: Bisous!
If a brand is about seducing your audience in an instant, Montreal has it all figured out. That pouty kiss says more than any hyperbole ever could. Paired with an ad campaign that promotes the city’s distinctiveness with the slogan “à la Montréal”—dance à la Montréal, cuisine à la Montréal, shopping à la Montréal—this branding is a prime example of how a city can leverage its unique qualities to set itself apart. —A

Brand Laval: Blocky but Good
Like many up-and-comers that are overshadowed by their sexy neighbours, Laval—Montreal’s oft-maligned suburb to the north—opted to market itself as a modern city in the midst of continued growth. The L-shaped cube, symbolizing Laval’s economic potential, is interesting, though it does remind me of Tetris. —B–

Brand Hamilton: Homage to Dr. Phil
Show me the marketing geniuses who came up with this, and I’ll show you a bunch of naked emperors. In a city known less for its potential to rise and shine than for its status as home to the nation’s first Tim Hortons, this was a disaster. Using a generic inspirational message for a city struggling for megacity recognition is like pouring Béarnaise sauce over a peanut-butter sandwich. No matter how uplifting, a marketing campaign alone cannot elevate a city’s culture. —