What I also love about Toronto is its historical buildings that's still standing but I guess not popular to most tourist because lots are obscured by modern structures already. I am not just after the beauty of the old structure but also the history behind.
The Massey hall is now a venue of variety of art forms, from classical music to world music and even international performances. It was given by the Massey family to Toronto and it can seat up to 3000 people. It is now a site of National historic importance in Canada and it was designated as a "Heritage property" by the city council under the Ontario heritage act. The walls of centuries are adorned by all artists who have performed there.
Massey Hall has got to be the best intimate venue in Toronto to see concerts / shows. Massey Hall first opened its doors in 1894 and has been operating ever since. The hall contains three levels - floor, balcony, and gallery. There is a bar on the very bottom level and a bar on the balcony level. A concession stand can be found in the gallery level. The most expensive seats can be found on the balcony level, right in the center.
I've seen a ton of shows here. Some of my fave shows at Massey include seeing the Kids in the Hall with Dave Foley and gang, Jane's Addiction, The Cranberries, Jerry Seinfeld, Jewel, Chris Rock, Barenaked Ladies, Lenny Kravitz, Harry Connick Jr., Stomping Tom Connors, Chantel Kreviazuk, etc. etc.