Well we're talking about riding here, not Thailand or Brazil. How about seeing it this way: Here everyone has a choice of what to drive. How many here choose to drive cars and wouldn't never even consider riding a motorcycle because they are far too dangerous? I'd say most. So choosing to do something that the vast majority of people perceive as incredibly dangerous is pretty "cool".
Some may see it as dangerous, but the bigger argument is practicality. A motorcycle is a poor all-round transportation choice not only because of climate reasons, but also because all the "stuff" we tend to load in our cars and trucks (including friends, family, children) simply wouldn't fit very well on most motorcycles. As a result, for most people a motorcycle's only practical value is one of recreational transportation. That means that motorcycles are and will remain a niche market in Ontario. Anything "niche" will tend to be viewed as "cool" by some, "pointless" by others, and not even given a second thought at all by the vast hordes.
As far as motorcycles being dangerous, much of that danger rests on the shoulders of the operator. There are a lot of long-time riders out there, myself included, whose riding careers over decades have involved no injury to speak of, and no crashes other than driveway drops either, and this despite all the supposedly poor drivers we share the roads with. I wouldn't call motorcycles inherently dangerous, but I do recognize that they expose a rider to more risk and adjust my riding to suit.
The "motorcycles are dangerous" thought really comes into play only when some hooligan intent on becoming an organ donor is seen hurtling through traffic as if it was a race. No doubt there is a pinhead contingent who thinks that kind of operation is cool, just as there is a pinhead contingent who thinks that Fast'n'Furious style street running in cars is cool. However, the majority of people out there just see it as stupid and uncool.
Back to the riders with relatively unblemished riding careers. If these people and their bikes are somehow cool, it's because they're "cool" in the same way that a convertible is "cool" on a nice day. Bikes, uncommon. Convertibles, uncommon. Jeeps, the real CJs with roof off, uncommon. Old classic cars and restored street rods, uncommon. Coolness comes from being uncommon, not from being seen as doing something stupid or incredibly dangerous.