Welcome to Hortland—a new column by WW's most storied freelancer, Jay Horton.

Each installment of Hortland will be wholeheartedly devoted to unearthing one of olden Portland's most obscure or beautiful or non-trivially interesting historical remnants, and then leaving it out to rust in the sun.

The first column concerns Kanye-proof grammy-winner Taylor Swift's first visit to Portland, age 16, to an old East Division Street juke joint called Duke's.

There are some who like to say Taylor Swift's heart was forever broken in Portland, on Halloween night in 2006.

A young Taylor Swift in Portland, with friend.
A young Taylor Swift in Portland, with friend.

Last week, Taylor Swift may have accomplished the greatest trick yet in a short life already overstuffed with casual miracles. She made the Grammys boring.

Though she was far from universally agreed on as the correct choice, her win for Record of the Year felt like such a fait accompli that even the dependably-outraged trolls didn't offer much more than a grumbling admissions that things could be worse.

Swift's acceptance felt both gracious and perfunctory. In the manner of royalty she appeared neither for herself nor for us, but out of humble respect to a perhaps outdated system. Even after learning that Swift was the first woman to ever garner two such awards, the commenting classes stayed conspicuously muted.

In part, exposes of Grammy cluelessness no longer move the radar. (If a blog post a blog post insists that Aretha Franklin had actually won fewer Grammys than, say, Adolph Hitler, would that seem so absolutely impossible?) Mostly, though, the award-watching throngs must've been stunned to discover this was only Taylor's second. That beggars reason.

Taylor Swift may well be the last true star whose star is still ascending. Her Grammy triumph appeared so resonant in part because the honors were bracketed by Adele's floundering and Kanye's dithering after Swift's perfectly-pitched remonstration. Control, really, is her gift. She's so effortlessly in command of her powers that feminist credentials lay unquestioned despite a trademark motif— date well, break badly, and spin resulting emotions platinum—that'd be at the least troubling in lesser hands.

Still, even for an artist who seemed to arrive fully-formed—one whose persona has not so much matured as coalesced—there are bound to be moments of growth best glimpsed through hindsight. Since essentially entering public life at the tender age of sixteen, her career has never stalled nor notably slowed.

All the same, at an outer SE Portland honkytonk nearly ten years ago, there's reason to believe that her sparkling engine might have found another gear.

A skull, Taylor Swift and the devil.
A skull, Taylor Swift and the devil.

On October 31, 2006, Taylor Swift was loping through the last gasps of relative anonymity.

She was already something of a cause celebre within the music industry—a songwriting prodigy who'd signed on with ambitious label Big Machine as a 16-year-old because RCA had wanted to nurture her slowly till the age of consent.

Compared to ordinary humans, she was maybe not famous, but at least dimly familiar after a recent bout of television appearances.

Although her self-titled debut, released just four days earlier, wouldn't chart until mid-November, she had criss-crossed the country over the past two weeks as a tourmate of Rascal Flatts. And while we won't pretend Taylor earned her wings on the road —literal wings, this Halloween night—these few dates will likely stand as the last times Taylor Swift will ever play to a crowd who doesn't already know who she is.

Swift had initially scheduled only a handful of shows around this period until providence cast her as sudden replacement for Eric Church after sets by the Nashville bad-boy du jour consistently ran past their allotted time. The Rascal Flatts gigs — Moline, Dayton, Omaha Bossier City — weren't exactly glamour spots, but they allowed rather larger audiences than she'd any hope of expecting at this stage of her career.

(She'd later bequeath Church her first gold record alongside a note that read: "thanks for playing too long and too loud on the Flatts tour.")

The rigors of a national jaunt forced Swift to cancel concert plans in the likes of Westchester, PA, but she kept a Los Angeles showcase with Gretchen Wilson. More curiously, although she'd played Memphis just three days earlier and was booked for Toronto November 1st, Swift stayed on a Halloween bill put together by up'n'coming sensation Jake Owen at a Portland venue not exactly known for breaking stars.

In 2006, Duke's Bar & Grill was also just starting out. Two years earlier, the Concept Entertainment group had purchased the desiccated shell of a venerable nightclub and set upon renovations—first attempting to re-brand the venue as Lotus East and then a more approachable incarnation of its shitkicker past.

Once named The Flower Drum and originally located on the other side of 137th and Division (which has since taken over by a Fred Meyer supermarket), the spacious honkytonk served as slightly-seedier companion to the nearby Division St. Corral dancehall.

The Drum eventually dropped the 'Flower', moved across the street, and tried as best it could to weather the diminishing appeal of their chosen idiom upon Portland proper. (An 80s version evidently introduced line-dancing to the state.) Duke's would briefly change formats again in coming years and only went back to the venue's traditional theme once the music itself had been sanitized — or, as owner Jeff Plew admitted, "once country dropped the western."

Owing to country's dimming cultural footprint around the area, we've no accounts of her concert save Taylor's own MySpace posting written at the airport later that night, and she mostly trilled breathlessly about the green-eyed heart-throb headliner. Any ordinary gig, that would be the end: an undeserving city's chance brush with greatness lost to the ages.

However, sometime soon after that Halloween — an unverified blogger pegs the date as early as November 2nd — the young artist began writing a new tune.

Debuting in concert early 2007, "Sparks Fly" felt different. Steeped in country signifiers yet more than a little bit rock'n'roll, the themes were overtly sexual for the first time while the lyrics seemed personal, specific, and damnably familiar:

The way you move is like a full on rainstorm

And I'm a house of cards

You say my name for the first time, baby

And I fall in love in an empty bar.

And you stood there in front of me just

Close enough to touch

Close enough to hope you couldn't see

What I was thinking of

Drop everything now

Meet me in the pouring rain

Kiss me on the sidewalk

Take away the pain

'Cause I see, sparks fly, whenever you smile

Get me with those green eyes, baby

As the lights go down

Although a recurring crowd favorite during concerts, the song didn't make second album Reckless, and, by the time it appeared on her third (Speak Now), edits had been made. A simmering banjo gave way to lightly-chugging electric guitar while the line about "falling in love in an empty bar" was replaced by platitudes about the lure of unwise behavior. Nevertheless, "Sparks Fly" was a born hit and singled out as a new way forward.

"Compared to the cultural juggernaut that was Fearless," wrote Slant music critic Jonathan Keefe for Country Universe, "Taylor Swift's Speak Now has underperformed at both retail and radio. The set's fifth single, 'Sparks Fly,' could turn things around for Swift, as it's perhaps the most perfectly constructed single in a career built on tracks that are marvels of pop production and songwriting … what makes "Sparks Fly" a standout is that it is, in a lot of ways, the purest iteration of Swift's template and repertoire … the narrative of 'Sparks Fly' doesn't necessarily scan as "country" in any archetypal way, but its simplicity and plain-spokenness parallel some of the genre's conventions. If Swift writes what she knows, what she knows better than anything else is the head rush of infatuation … "Sparks Fly" plays as a template as much as it does as a standalone single, and it's a testament to everything Taylor Swift gets right."

As with all of her albums, the Speak Now CD booklet held codes for acolytes to decipher. Within the lyrics, some letters would be capitalized at seeming random, and, taken together, they'd spell out a clue betraying insight toward the actual meaning of each song.

For "Sparks Fly", the message read PORTLAND OR.

This has been told before, of course, but softly. A few of the relevant websites performed due diligence to track the origins of her Speak Now coding, and Tumblrs the world over re-post the original MySpace flutterings.

Still, given the relentless media appetite for all things Swift, it's odd the events haven't really ever been revisited. The span between creation and release of "Sparks Fly" rather dulls gossip-mongering, as she likely knew, but doesn't the oddly-over-extended gestation of a certain hit (which she surely knew) suggest something decisively buried?

Taylor has no reason to ever discuss the subject beyond labeling it pure fantasy, and, considering their eight year age difference, Jake Owen has considerably less.

Still she'd already begun twinning songs to former paramours — Joe Jonas, Jake Gyllenhaal, Taylor Lautner, and John Mayer … many, many about John Mayer (who was, as happened, 12 years older) — and, when pressed for details during the single's release, Owen did quip "I'm glad I'm the reason she sold a million this week."

At the end of the day, since speculating upon romantic frisson would be tantamount to allegations, the hottest-button to push would be defining that remembered Halloween as first flush of womanly passion enlivening a repertoire then mostly admired for preternatural cleverness, but arguing authorial intent isn't really the stuff of tabloid reportage. Swifties, for their part, dare not look too deeply outside the established mythos. Her early adoption of celebrity 'shipping applied an indelible patina of truth to each song of love and loss while simultaneously imparting a plasticine gloss never to be taken so seriously. In that context, any tales of Taylor crushing forcibly on a b-list headliner 'midst sound check somehow appears both absurdly fantastical and too grimily real.

Mostly, though, the story just feels wrong. Portland should play no part in the Taylor Swift story. While there's artists aplenty who've less in common with our over-educated, awkwardly-beautiful, hopelessly-white-bread town, the concurrent cultural ascent of Tay-Tay and Portlandia seem to have happened in different universes. Has a dominant pop star ever been less weird? Have any so thoroughly understood indie cred while reflexively rooting against? She's painting personality on ambition, we're insisting professionalism lies behind quirks, but they're near enough the same corner to draw conflict. And, though authenticity's no longer exactly a strength of either entity, it it any easier to imagine Taylor at home in a country bar or a country bar at home in Portland?

We first found out about Taylor's visit while researching the truth behind "Portland, Oregon" — the 2002 Loretta Lynn/Jack White garage country ballad describing a sloe-gin-fizz-fueled affair. While hitting radio stations up and down the northwest during her long attempt to break away from the northwest, Lynn would surely have frequented The Flower Drum, and a veteran area bar owner seemed to recall the club offering the song's supra-distinct tipple as a regular special.

One of Lynn's auto-biographies shrugged off the story as tourmate-inspired, Holiday Inn-set hi-jinx meant to spoil her husband's golfing trip, but that explanation doesn't really make much sense. The prank couldn't ever have seemed remotely funny, Holiday Inn don't often serve pitchers of sloe gin fizz, and Lynn was famously prone to the fraudulent overshare setting up her lifemate as fall guy.

In our heart of hearts, we'd like to believe that the site of The Drum and Duke's stirred the last temptations of Lynn and Swift and, hell, D.B. Cooper.

Even limiting ourselves to the dully real, it's still more than passing strange that the (indie-rock-fueled) effective swan song of the long-reigning Queen of Country and de facto statement of pop principles from a budding Empress of The New were both dedicated to a city busily disappearing all evidence of humbler origins.

Far more than promising romance, this 21st Century Portlandia has, for better or worse, become an emblem of reinvention. And country is the past — the foreign past. They do things differently there.