Place #2!
These will henceforth become shorter. The quality of my educational output demands it.
Here is a place I love and actually frequent. The Kitty Cat Klub in Dinkytown fulfills a lot of my needs. A good happy hour (4-7 daily, lots of 2 and 3 dollar things), good atmosphere (in terms of layout, lighting, couches), and live music most nights (of varying quality, mostly local). I saw Jamie Ness (Duluth native and one-time City Pages Picked-To-Click artist) for the first time in about 4 or 5 years last month. Nostalgia and good songwriting can make for a sublime evening. Can be a bit of a hipster hangout, which can be good or bad (you might find that comes up frequently in my recommendations).

It’s also a good place to meet interesting people or maybe run into people you know. Like Molly or Tony (he’s #3).
