It's not trendy, it lacks identity, and half of it is a family venue. But....
Jack Astor's may very well have the absolute best service I have ever experienced in Calgary. I frequent the place due primarily to proximity. The service has been consistently excellent. I was starting to forget what good service was like. This is actually becoming a commentary on the state of hosting in Calgary, but Jack Astor's really reminded me of how much positive attitudes and friendly staff go a long way to enjoying your night.
Beer selection is good. Not great, but good enough, with a variety of non-big-beer options to choose from. Granville Island comes to mind. The food is interesting--it's kind of hit and miss. Some items are brilliant and healthy such as the affordable $12 Lamb Kafka. Other things are a little bewildering, such as $14 chicken fingers and fries. The pizzas are good, at around $13 for what appears to be a 10" (more than enough food) with a healthy dosage of toppings. I recommend the Spolumbo's.
So, in the end, if you want to be absolutely blown away by service or simply reminded of what good hosting looks like, give Jack Astor's a try. Sit in the lounge and watch the bartenders practice their flair. Watch the game on their multitude of TVs or turn your attention to some FHV-style videos on the aux TVs. You might just have a fun.