Image: Betty Turbo

The definition of a “classic” Portland bar depends on who you are. Some might extol magnum-size martinis at the Benson Hotel’s Palm Court, and the illusion that Raymond Chandler will soon sit down opposite you. Others prefer shots at The Slammer, where Inner Southeast retains a Christmas-light-festooned, give-no-damns élan otherwise vanishing. Yet another contingent would rather cross the street to Rum Club, a place still in its first decade, where a highly engineered nouveau-tiki gestalt angles for insta-classic status.

That these clashing worldviews coexist in Portland only shows how tricky superlatives can be. A true local classic must tell a story about the city—what the place is, or was, or could be. Trick is, those stories may contradict one another. What matters is that the essential bars mark the city’s changes—or, even better, defy them.

Two recent after-work stops, for example, told contrasting true stories. Liberty Glass, sleepy on a rainy afternoon, made an all-too-obvious parable of gentrification, development, and urban densification. Opened in 2008, with the global economy a wreck and North Mississippi still something like a village, LG now abides in the literal shadow of looming apartment projects.

Miraculously, the 1910 bungalow survives with its favored Haunted Huntsman’s Retreat aesthetic: an ode to a broken old port town, where you might fall into casual bar-side conversation about river piracy. The story this place tells could be one of quiet resistance to powerful forces. It may not be now, but it’s Portland!

Or is it? On another afternoon, I happened in Teardrop Lounge, opened in 2007 by cocktail ace Daniel Shoemaker. Teardrop offers all the atmosphere of a generic upscale hotel lobby—with its chrome/concrete look and jazz-hop soundtrack, it’s how you’d picture a place in the Pearl District if you’d only read mid-2000s Portland Mercury articles about the neighborhood. But the thing is, the drinks are stellar, the service all-pro. As I slowly absorbed a drink called the Italian Job (a creamy mixture of Ransom Old Tom, Strega, apricot, and lime, warmed up with Calabrian chile tincture), I pondered a different city’s story: that of an ambitious place, determined to rise and not too fussy about history. It felt just as right and as good.

Again, that’s just two dimensions in Portland’s tipsy multiverse. Every dive on upper NE Glisan could play host to a gritty one-act dramatizing a working-class city shifting eastward. (Try Top of the Hill.)

Some bars we mostly can’t go to—members-only deal dens like the Arlington Club or the Multnomah Athletic Club’s secretly sweet sports pub. Exclusivity always tells you a little something, doesn’t it?

If there’s any through line to our collective boozing, perhaps it’s that we love our old haunts and their fight to survive. A swaggering dive like the Alibi, a rum-rocked postwar island fantasy established in 1947 and recently given the right kind of makeover by the rehabbers behind Sandy Hut, reassures us. The city may be changing, but we’re not completely losing our souls. Right?

The most important local bars may be the ones that help us anchor our own stories, and sync them with the city we love. Twenty years back, fresh from the Montana wilds, I stepped into the Mallory Hotel’s Driftwood Room. Then, as now, that woodsy arc of midcentury modernism could transport you directly from daylight to a dark, sexy after-midnight. Hello! So this was life in the city.

The Mallory sold and lost its name. But the Driftwood, no one dared change. I hope one might say the same of some corner of my soul. I’m going there now, to make sure it’s still there.

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