Fairytale of Old Portland
Nov 14, 2024
A love letter to a less shiny city, and the teenagers, insomniacs,
and eccentrics who populated it.
by Ben Coleman
It was December 25, 2013, and everyone in the gay steakhouse was getting amiably drunk.
It was one of those Portland winters that was cold and wet and absolutely miserable to be out in, and I had to work. But before that I was going to pre-spend my holiday pay on a fancy dinner—or at least the fanciest dinner I could afford working the graveyard shift for a bit more than minimum wage. Starky’s was what you’d affectionately call an “establishment.” It wasn’t a dive, but it was dive-adjacent: Formica tables, napkins for coasters, stately framed prints of drag queens and bodybuilders on the peach pink walls. In the summer they ran a raunchy charity car wash you could hear from blocks away. In the fall and spring, the iron-fenced patio always had a handful of elegant old swains sipping cocktails while they watched the world go by. In the winter they were open on Christmas Eve.
People who go to bars on major holidays often exist on the margins of society. Drunks, malcontents, lost souls estranged from religion or tradition, those who have no family or are burdened by what family they have. And folks who just can’t afford not to work. I didn’t take an inventory of my fellow travelers, but I’m sure there was the usual mix of those usual suspects, along with the clientele of a relaxed neighborhood gay bar: pretty Midwesterners with sad eyes, pairs of middle-aged husbands who didn’t want to cook, the aforementioned swains. Some were socializing like it was an office holiday party, others were lost in thought as we studied our mashed potatoes for clues to the human condition as freezing rain whipped against the windows. I’d like to say that “Fairytale of New York” came on the jukebox and we all got misty and sang along, but I suspect if anyone made a move to change the Britney Spears music video on the wall TV there’d have been a riot. But I still left feeling better about the world.
“Old Portland” is a moving target, but it’s not ephemeral. It began when you found somewhere in this city that welcomed you and ended when it was torn down to make way for a condo. Townies my age wax rhapsodic about all-ages music venues like La Luna and Meow Meow, about the Church of Elvis, the terrible service at The Roxy, stiff drinks at Club 21, late night LAN parties at Backspace. We like to talk about how you could smoke in bars, even though most of us have long since quit. But previous generations had their own haunts and hollows: jazz clubs and punk houses that lived and died and exist now only in memory. It’s not like they sold tickets to Old Portland and we’ve got the stubs in a shoebox somewhere.
What I suspect we’re all nostalgic for is the feeling, however subjective, that the margins of society were a bit wider, and more people could afford to exist in them. That Portland was not a precision machine. It had looser tolerances than today. There were poorly-optimized businesses in the service of teenagers, insomniacs, artists, and eccentrics, alongside the usual cadre of office workers and serious restaurateurs that all cities need to function. When those places went away they were rarely replaced. Willamette Week’s Aaron Mesh once wrote, “Every generation gets the ruining of Portland it deserves,” and it’s as true today as it was in 2015 when they tore down Starky’s to make way for the 46 modern apartment units that sit there now.
Cities change and culture shifts. Style moves from hard forms to soft, sarcasm makes way for sincerity, the rebels sell out and so on. But these cycles aren’t arbitrary. They are shaped by market forces and public policy. Coffee shops used to have couches so that people would hang out in them, fill those spaces with the sounds of awkward first dates and someone scribbling the first chapter of a terrible novel. Coffee shops aren’t soft anymore. They’re full of angular, industrial surfaces, because to make rent this month they need several hundred people to buy eight dollar macchiatos and fuck off somewhere else.
The Portland of today is shinier than the Portland of my youth. There are luxury retailers and well-moisturized influencers and futuristic cube houses with two-Cybertruck garages. Presumably this was done because the hippie granola markets and communist bookstores and neighborhood dives that were already here don’t pull the property taxes needed to fund a proper 21st Century metropolis. Our city fathers promised us prosperity if we’d only sacrifice a couple of eyesores on the altar of urban renewal and mixed-use development. It’s a bargain many willingly made, perhaps believing that for once in human history the rising tide would lift all boats. The bodies of the displaced lying in our streets seem to say otherwise.
Someday this city will be a vast and uniform sea of tasteful residential buildings named after the ugly and interesting places they replaced: the needle parks we walked past on the way to school, the cart pods where you could get a pretty good gyro, bars like Starky’s where neighbors gathered on holidays in defiance of the shitty weather. They’ll have large matte photos in the lobby of musicians who couldn’t afford to live there and gig work security guards to shoo away any indigents who get close to the property line. That’s progress, I suppose.
We miss Old Portland not because it was cheaper or somehow more authentic, but because of the people it once accommodated. We miss the sense of community that animated those old, demolished buildings, that warmed them in the way that only old buildings full of people talking can be warm. Every day we’re tested, and no more so than during the holidays, by how we welcome the strangers in our midst. I was a stranger once and found welcome in a neighborhood bar that’s not there anymore. I hope it can be found again somewhere new.