Bleh. La Distillerie is one of these places that you will always hear about in Montreal but please do not feel guilty if you haven't tried it yet. Not highly recommended.
First, do not - DO NOT - take the risk to come and wait in line for a heavy rainy night. There comes the first con: the place is surely small and breathable thanks to the golden rule of one out = one in. You can wait a long time.
Then once inside, surely the interior is charming (still feels like a pirate amusement in Disneyland at some point) but the atmosphere is quite common. Nothing special music wise for example. Certainly the drink menu is extensive but I didn't find their cocktail that good. Lots of different fruity flavors, too much hard liquor in it (a problem taste wise) and despite how many are there, I always had the impression of ordering fruit punch in empty jam pots - well actually that's cool I'll admit.
Overall: too much enthusiasm for this decent spot. Go there freshman and invite low alcohol tolerance mates.