^My point is that if you want to talk about being "cool" - however dumb that objective is - you can't just give yourself that label or else it sounds like something Dads do "I'm cool with these cool sunglasses!" You have to be considered cool by outsiders. Montreal in 2005, was considered cool by outsiders because of its music scene. It was the 90s Seattle of the 00s. And no, I don't think a music scene is the only indicator. But Toronto, currently, is not being written up as any centre of hipness with any sort of regularity. (About the closest is something like
this. Just a few more pieces and we can consider it a trend rather than an anecdote.)
(BTW your assumption that I don't like hip-hop is weird. Toronto's hip-hop scene is big in Canada, but it is not blowing away Americans, with the exception of Drake and maybe Kardinal Offishal.)
And compare the depth of reporting about Montreal in 2005 in the NYT - it gives specific details - with the bland, tourism-focused reporting of the HuffPo piece. I wouldn't be surprised if Toronto Tourism had actually paid for it!
I think Toronto is amazing and wonderful and all that. But let's have some perspective on how other people judge our city.
And I think this is part of Toronto's problem. My NYC friends ask me - what makes Toronto different than other North American cities? Or, what would make us visit your city rather than another? For Montreal, that question is easy - Montreal has smoked meat, bagels, crazy drivers, strip clubs, stylish boutiques - but for Toronto, it is harder to come up with things that truly differentiate us. The things we can really crow about, like having a livable downtown core and a general open-mindedness about immigration are great for people living here, but they don't really scream: come visit!! Possible aquariums and the Toronto Island and everything else are great, but how is this particularly different than other cities? We need to start focusing on figuring those things out rather than getting offended when someone suggests we could be doing things better and currently Americans think we're nice but aren't that crazy about us.
I do think the Scott Pilgrim movie will have a huge effect, tho. And BSS and Drake are big ambassadors for Toronto.