Live music, make their own Beer or excellent beer selection. Recommendation for out of towners needed.
Bellwoods Brewery on Ossington if you're okay with trying to muscle out hipsters at communal tables for seating after waiting an hour and a half in line.
Granite Brewpub at Mt. Pleasant and Eglinton if you'd like to actually sit down in peace when you get there and enjoy a good beer. (FYI: their Peculiar is one of my favourite beers anywhere.)
I cannot off the top of my head think of anywhere that hits both notes here, most live music venues tend to have a relatively pedestrian beer selection. When you say live music are you after rock, jazz, folk/acoustic indie or something specific?
Absent any other guidance I would just go to the Horsehoe, well because it's the Horseshoe, arguably the most important non-jazz live music venue in North America that is still in operation.
If memory serves they also have an acceptable draft selection at the Cadillac Lounge in Parkdale, not great but acceptable.