The exterior of the Oakwood 83 Bar and Grill
Oakwood 83, open until 4 a.m., just like the sign says

Since I moved north to Lincoln Square last summer, I’ve walked past a bar every morning on my way to the Brown Line that, quite honestly, hasn’t looked like it needed to be on my must-try list. I mean, for Pete’s sake, there’s a piece of paper taped to the window that reads, “For your protection, these premises are being video recorded.” None of the bar’s many neon signs promotes a beer that could be considered remotely fancy, and so far I haven’t been in the market for “STEAKS,” another prominently advertised feature.

A cautionary sign at the Oakwood 83 Bar and Grill
Recorded for your protection

Never say never. Last Friday night we were celebrating a friend’s birthday at Fountainhead, and when we’d had our fill of the pricey beer—or maybe Fountainhead was closing for the night; I honestly can’t remember—we found ourselves shivering on the sidewalk, gazing across the street at the Oakwood 83 Bar & Grill (1959 W. Montrose Ave). “Well, let’s give it a shot,” I’m pretty sure I suggested.

We walked in—it must have been 1:30 or 2 a.m.—and froze. The two patrons leaning on the bar swiveled to give us the barest of assessments; the jukebox was utterly silent; and the multitude of upholstered chairs on wheels (think Olive Garden meets 1970s banquet hall) were as yet unoccupied. We hovered near the door until the bartender finally called across the room, “Hey, you guys want a drink?”

“Um, are you about to close or something?” I asked.

“Nah. We’re a 4 a.m. bar,” he said with a grin, beckoning us to place an order. (It was a conversation that would have been unnecessary had I taken a harder look at yet another of the bar’s signs.)

A few Bud Lights later—yes, Bud Lights, and I don’t want to hear it—The Creative Director and I started begging for dollars. “Please, please,” we beseeched our friends, even Liz, whose birthday we were celebrating. “We need dollars for the jukebox! Doesn’t anybody have any dollars?” Several bills materialized, including a badly torn one, which we repeatedly tried to force into the machine. A varied crowd of surprisingly youngish people began to stream into the Oakwood just as our brilliant playlist began: Def Leppard’s “Pour Some Sugar on Me” (so obvious, sorry), “Good” (Better Than Ezra), “Love for Sale” (Talking Heads), and my pick, G&R’s “Patience” (I am an A-plus whistler).

Surely to the chagrin of our fellow barflies—and by this time there were lots of them—we sang, we danced (mostly twirls and dips), and we engaged in a fairly consistent level of PDA.

And then there were the shots. Something with Baileys, followed by—what? Patrón, maybe? Attention, please: If you’re reading this, and you’re 23, and you need a trick for feeling at least 1000 percent better the morning after a night out, heed The Chaser’s number-one rule: Never do shots.

Never do shots. And if you catch me breaking my own rule at Oakwood 83—my new favorite kinda-seedy 4 a.m. spot down the street from my apartment—go ahead and remind me.