Rachel F.
Yelp
Did you know this is the second oldest bar in MKE? Well, it is, and according to a few reputable(ish) sources, too.
As a rule of thumb, I've always tended to shy away from the Uptowner. It's always seemed a little TOO real, a little TOO gritty, a little TOO boozy... I mean, c'mon. I'm not averse to getting real, but sometimes this place is a little much, even for me.
A recent visit, however, prompted me to take a look at the old charm school (self-appointed, tongue-in-cheek) with a fresh set of peepers. If you've never been before, take a look around... the place appears and actually is rather hip, at least when it comes to décor and ambiance. Disaffected Riverwest cool with interesting paintings/art/old photographs on the walls, dark red interior, a wicked rad ceiling pattern and texture, a Guns 'N Roses pinball machine, dark woods... hey! This place reminds me of Sabbatic in Walkers Point, sort of. Alright.
Cheap drinks. I advise bottles and cans over taps just because I don't trust beer lines implicitly. Also, mixed drinks here can, to quote friend and elite Yelper Joseph S, "strip paint off of just about anything."
And it's right then that you notice the really, really weird conversation to your left, and the man who's most likely homeless to your right... he's sleeping on the bar. And you're not judging, just observing, so you take your 2-fer-5 Point tallboys back to your table and watch the show. This is the grit. THIS is why you don't come here too often, even though you like to keep it real. It is real. Also, the place is kind of yell-y.
I understand the Uptowner has some really fun "theme-ish" nights (hip hop DJ night, I think they used to have a metal night, too) and overall, I really like it for what it is: an historic, gritty, Riverwest dive with cheap drinks and an abrasive reputation. (I like to think the Uptowner's secretly a softy with a big heart, though.)