Mackenzies is a sports pub right across from High Park. It's only been around for about eight years, but it has that comfy, worn-in vibe that makes you feel like it's a worthy neighbourhood drinking hole and hang out. Vintage pics of the trifecta of cool - Hendrix, Monroe (as in Marilyn) and Lennon - are on the walls.
The bar hosts Euchre nights on Thursdays and open mics on Saturdays. As for food, the manager there tells me there is only one item on the menu he wouldn't recommend, but you'll have to eat your way through it to figure out which it is.