Back in my University days I would often see the late great Stan Rogers in concert at various bars and coffeehouses around town. Loved him, and he was gone much too soon.
I saw the Barenaked Ladies back before they hit it big (and again twenty or so years later)- lots of fun. I think I preferred the earlier one, when they were a little less "polished".
Great Big Sea gives a great energetic concert.
A few years ago I saw Sting during his "Symphonicity" tour. A lot of fun, and some fresh new takes on his hits with the orchestral accompaniment.
Among those who haven't really made it big yet, Heather Dale has some lovely songs and has performed in some lovely concerts.
A favourite singer of mine died last week- I used to look forward to his performances every year. RIP Owain Pfyfe