Calgary is boring because everybody is working in boring industries. Calgary is all manual labour jobs like construction, warehousing, factories, heavy industry. Even the support work in the offices and retail is focused on the heavy industry. It's boring. When those type of workers have free time, all they can think of doing is drinking beer and listening to crappy music or going to see a hockey game. Or leaving town to go do something interesting.
There are hardly any artists or musicians in Calgary. Sure, it's a regional cultural centre, but that's because there's nothing else around there to compare it to. Red Deer? Edmonton? Butte? Moose Jaw? Come on.
There is too much work in Calgary for it to be an interesting place. You can't have both. The type of work there is not particularly conducive to creative minds.
The city is not designed to be interesting. All those one way streets, boring Stalinist buildings... downtown is full of petty drug dealers and crackheads. No wonder people only go there to get drunk at night, then go home to their wooden ranch houses 30 kilometers away.
Did you notice the grownups don't even go out at night? I mean people over the age of 25 or so. Only drunken kids who don't know any better find Calgary nightlife interesting.
Don't get me wrong, Calgary is good for some things, like work, and at least part of this country needs to do some hard work. Also, the people are friendly and the air is clean (compared to Toronto & Montreal). But if you want to have a good time, go where the people are not focused 100% on their jobs.
Lived in Toronto, Ottawa and Calgary