Perhaps all of Portland's drinkers can be lumped into two groups: O'Brien's (519 NW 21st Ave., 223-5390) people and Wimpy's (521 NW 21st Ave., 223-5153) people. The two cozy bars, attached at the proverbial hip via a slim hallway, feel quite different despite their proximity to and friendliness with one another. O'Brien's, which recently underwent a classy, burgundy makeover, is where you go to catch up on the gossip and sip Jameson with a small group of friends. The club's garage-style front windows are ideal for people-watching, and the nachos are dope. The more cavelike Wimpy's, on the other hand, is where one goes to drown their sorrows alone, and maybe watch a movie on TNT with the volume off, some semi-ironic yacht rock playing softly on the stereo. Wimpy's is clearly the hipper of the two establishments, but dammit, I'm an O'Brien's man. That's a cross I'll have to bear for the rest of my life.
WWeek 2015