If you are ever in Stittsville (a suberb of Ottawa), there is a barbershop (Link to Website) That has the conversation flowing, they have a foosball table and ... they offer you an espresso while you get your hair cut.
It's a great little place ... but you need to cover your cup so that you never get hair in your coffee.
That place looks like fun! My friend and I found a nice shop in Montreal the last time we were there (Belgard) It's more of an old fashioned place, they offer you a whiskey when you come through the door.
NICE!!!
There also used to be a topless barbershop in Montreal as well. I'm not sure it's still around though.