Lots of great concerts listed. Here's a few that come to mind, not in order of preference. I'm guessing my list would fall in the eclectic category.
George Shearing on piano with Neil Swainson on bass in a small cafe/tea room, Toronto, 1980s. 50 people or so, on a Sunday afternoon. Amazing.
Muddy Waters at the Colonial Tavern Late 1970s. Legendary performance. Had a table right next to Pine Top Perkins on piano, casual conversation with Pine Top and Muddy (separately) between sets.
Todd Rundgren at the El Macambo tavern in Toronto. Table in front of stage, feet on the stage. Tickets for 2 shows in one night. (had the great seats for the second show).
Emerson Lake & Palmer at the Olympic Stadium, Montreal 1977, with 63 piece orchestra. The orchestra was brought in for the first show of the tour then scrapped due to cost. They brought it back for Montreal which was the last show of the tour. General admission. Amazing performance. 30 yard line centre in relaxed Quebec atmosphere - sitting on blankets, taking turns going to fetch 18 Laurentide Ales at a crack (18 was the most one could carry - 6 per tray, 3 high) without spilling. Finding the car after foreshadowed a well known Sinefeld episode. The big O stadium is roughly a circle/oval. 7 floors of parking. Our group split up after some time and had it 4 levels and been there 2 hours when it finally emptied out enough for us to find the car. Memorable.
Beethoven's 9th, TSO, Yukka Pekka conducting, Mendelssohn Choir First 3 times I heard this, with Yukka Pekka conducting. Still my favorite symphony or classical piece. I get choked up every time I hear it live (If a good performance) when I hear and feel the beauty of the music and think about the incredible adversity Beethoven faced while producing it.
Stranglers at the Masonic Temple Couple of times in the 1970s. Fantastic band live.
Iggy Pop Saw him a couple of times at small/medium sized venues in Toronto. Difficult to match his performance energy and some great songs.
Mel Torme at the Imperial Room, Royal York Hotel 1985-ish. Dinner & Mel Torme -what's not to like.
World Scottish Highland Tattoo, Canadian National Exhibition Stadium 1975. Showing my heritage a bit here. My grandfather was in the Gordon Highlanders and Cameron Highlanders in WW1, and the Black Watch after. His first regiment was folded into the second because too many were killed to keep going as a single regiment. They fought in kilts, in trenches for the full war then stayed to clean up 6 more months, so they were in France from 1914-1919. My grandfather was also a top level piper. When he couldn't play anymore (mustard gas was hard on the lungs) he sold his pipes to a Pipe Major, who played them while marching up the beach at Normandy. These regiments are made of tough dudes. They and the Gurkhas were put across from the worst German positions. It was the Gordons who, as infantry, cleared the coast road of mines and marched into Tripoli while Montgomery was kicking Rommel's ass across North Africa. Not just guys in kilts playing music on a field but hundreds of years of valiant history, and real men in kilts playing great, stirring music on a field.