1. Elliott Smith, "Rose Parade" (1997)
When Elliott Smith wrote about Portland, it was often with an eye toward those corners of the city most would be content never knowing existed: the drug dens along Southeast Powell, the cracked streets of Alameda, the sad fairgrounds out past Condor Avenue. In "Rose Parade," Smith gets dragged down to one of the town's most popular civic traditions, and it sounds like he'd much rather be at the drug houses, or anywhere else. Everyone is shouting and jockeying for view. He gets pelted by candy disguised as money, and trips over a dog. The marching band is ridiculous, and the trumpet player sucks so bad he must be drunk. In interviews, Smith described the song as being about the facade of self-congratulation, and the line "everyone's interest is stronger than mine" is often read as a sick anti-Portland burn. Indeed, it's something like a Dear John letter to the city: After the success of Either/Or, he'd move to New York, then Los Angeles, where he ended his life in 2003. But we shouldn't take his disillusionment personally. In the final lyric—"When they clean the streets I'll only be the only shit that's left behind"—Smith betrays what "Rose Parade" is actually about: the feeling that, maybe, there's no place you actually belong.
2. Sleater-Kinney, "Light Rail Coyote" (2002)
Oh, sure, they say there are "no cities to love" now, but back in 2002, the ladies of Sleater-Kinney seemed awfully infatuated with at least one. Using the true tale of a coyote that once tried bumming a ride on the MAX as an entry point, "Light-Rail Coyote" mythologizes Portland as a millennial frontierland, where nature and urbanity are practically indistinguishable from one another. Written by a band that immigrated down the I-5 from Olympia, Wash., the mountain-sized riff that accompanies Corin Tucker's breathless verses is charged by the ecstatic possibility that awaits on the other side of the Columbia—in the diners and bookstores, the strip joints and punk clubs and, of course, that great "dirty river." Coming in the middle of One Beat, an album thoroughly coated in the ash of 9/11, the song positions Portland as a beacon of hope for anyone still wanting to live wild and free in America. Don't ever let anyone tell you the weather is all there is to care about.
3. The Wipers, "Doom Town" (1983)
Nowadays, the chief source of angst in Portland is the sense that the city is changing too quickly. In 1983, though, a young Greg Sage might've delighted in the sight of a few new apartment complexes or upscale brunch spots on his block. All right, probably not. Still, if the Wipers' intensely stormy punk was reacting to anything, it was the existential inertia of life in Old Portland, and that theme is central to "Doom Town," Sage's harrowing sketch of a dead-eyed metropolis where "nothin' ever changes" and "you can never win living innocent." Of course, that is precisely the kind of environment that breeds independence, and while Portland is not as doomy as it was, the do-it-yourself ethic Sage embodied remains part the city's DNA. Because, really, what other choice do you have?
4. Cool Nutz, "Portland Life" (1997)
By 1997, it seemed like every major region of the West Coast had elected its rap ambassador. L.A. had Dre. The Bay had Too Short. Even Seattle had Sir Mix-A-Lot. With Harsh Game for the People, Terrance "Cool Nutz" Scott elected himself Portland hip-hop's Mayor for Life, and as an inauguration gift bequeathed upon his constituents an anthem to finally call their own. To its credit, though, "Portland Life" is that it doesn't carry itself like an anthem. From the whistled synth line to the casual delivery, Nutz and his homies G-Ism don't seem overly concerned about whether or not outsiders buy the assertion that "these Portland streets ain't nothing nice"—which, of course, makes them all the more convincing.
5. Loretta Lynn and Jack White, "Portland, Oregon" (2004)
Sorry to burst the bubble, y'all, but no bar here serves sloe gin fizz by the pitcher, and Loretta Lynn almost certainly didn't bang Jack White within city limits. While the pair played coy about the song's origins after it became a hit, in her 2002 autobiography, Lynn confessed to coming up with the lyrics, describing a tryst sparked in a dimly lit tavern, in a fit of annoyance with her late husband, after he stuck her in a local Holiday Inn and went golfing—which means the most famous tune to ever namecheck fair Puddletown could've just as easily been titled "Kenosha, Wisconsin" or "Paramus, New Jersey" or, God forbid, "Medford, Oregon." But what does it really matter? With White's scorching slide guitar sizzling under the country diva's ageless vocals, the Grammy-winning collaboration cast Portland as a place of deliciously illicit romance, where the bars keep our secrets hidden in their dark corners. If that ain't lovely mythmaking, then what the hell is?
6. The Replacements, "Portland" (1988)
With the Replacements, awesome and awful were always a package deal. Want to see the songs that saved your life played live? Better prepare to sit through a lot of sloppy Stones covers, too. When they rolled into Portland in December 1987, though, at the very end of the Pleased to Meet Me tour, "awful" is all they had left in them. Arriving at the old Pine Street Theatre, functioning on one hour of sleep, the band proceeded to get roaring drunk, fuck up the backstage area, then stumble through a show so bad it entered into fan lore, with the attendant misremembrances. (One fan swore to me that Tommy Stinson leapt through a plate-glass window and ran screaming down Sandy Boulevard; no one else recalls this.) A year later, Paul Westerberg would apologize in the form of one of the Mats' best late-period songs, a countryish ballad with a refrain that looks back at that disastrous gig and laughs: "It's too late to turn back/Here we go, Portland!" Alas, it got scrapped from 1989's Don't Tell a Soul and didn't surface for another decade, long enough for everyone to forget what it was apologizing for. But Westerberg never did: In April, at what'll likely be the Replacements' last time in town, he pulled "Portland" out of the mothballs, and issued one final "we're sorry."
7. Viva Voce, "Rose City" (2009)
As you may have already noticed, by the time most artists get around to writing their "Portland song," the bloom has come off the rose, so to speak. But "Rose City," the title track from the transplanted Southern psych-rockers' penultimate album, is such an unabashed expression of civic pride it's a wonder the Timbers Army hasn't adapted it into a chant yet. Not that the band ignores the bad, they just concede that it's inextricable from the good, and decide to throw their arms around the whole glorious mess. "I wanna go back where the rain won't stop/And where the trees run wild like killer cops," Anita Elliott sings with dreamy wistfulness, before crunchy alt-rock chords hammer down in the chorus. Singer-guitarist Kevin Robinson has said the song is "meant to be more of a nude painting" than a valentine, but what's not to love about seeing your town stripped to its warts?
8. Helio Sequence, "Everyone Knows Everyone" (2004)
Leave it to some native Beavertonians to capture the strange ambivalence toward Portland anyone who's lived here long enough seems to experience at some point. Wrapped in both earthy harmonica and electronic whooping, singer Brandon Summers breathily vacillates between wanting to break out of this small town in a big city's clothing, where "everyone knows what everyone's doing," and resigning himself to staying put and enjoying the sun when it comes. "There's no escaping," he sighs. "There's nothing to escape."
9. Michael Hurley, "Portland Water" (1991)
Believe it or not, some of us actually moved here for the weather, and oddball folk hero Michael Hurley makes the cold sound awfully enticing on this languid back-porch ditty: "Up in the canyon lookin' down on the river and it makes me shiver/Oh the call up to Portland on the public telephone/Says it sure is rainin' here in the state of Oregon." Damn right, it is.
10. The Decemberists, "On the Bus Mall" (2005)
In which Colin Meloy stops singing about dirigibles long enough to pen a sweet, cascading tribute to Portland'€™s homeless youth who huddle together "€œon the colonnades of Waterfront Park" to survive the chill of the night.
11. Kind of Like Spitting, "Aubergine" (2005)
Man, and you thought Isaac Brock had issues with Portland. Ben Barnett's scathing declaration of tough, er, love, goes beyond the "human turds," directly calling out the city's music culture ("so many songs sung in shrill thinning tones"), the "thriving upper class [that] just can't be bothered" and, well, this paper ("the weeklies are just trash"). That it's set against a shuffling folk arrangement overlaid with twee flute takes a bit of the sting out, but only a little.
12. Illmaculate, "Lost Our Soul" (2012)
Illmaculate is Portland's best battle rapper, but when he's not shitting on someone's mama, he's acting as the scene's conscience; see the Blue Monk Incident of March 2014, when he sacrificed his own show to bring attention to the city's literal policing of hip-hop culture. On "Lost Our Soul," the St. Johns-repping MC tackles another hot-button issue—gentrification—watching as the forces of capitalism "turn our buildings to dust." The tone is of ache more than anger, but there's also resilience in Chase Moore's towering beat, and enough soul in Ness Lee's chorus to convince you that not all is yet lost.
13. Derroll Adams, "Portland Town" (1957)
A compatriot of "Ramblin'" Jack Elliott and student of Pete Seeger, the late Derroll Adams was indeed "born in Portland Town," in 1925, and entered the folk canon three decades later with this simple, chilling banjo tune that's both a protest song and murder ballad. In under three minutes, Adams' narrator gets married, has children and sees them off to war, where each is killed, easy as "one, two, three." In the final verse, he vows to never have kids again. But "Portland Town" bore its own fruit, being covered by Joan Baez, the Kingston Trio and Marianne Faithful, among many others, and while Adams' name is only known in the households of hardcore roots aficionados, those admirers include Paul Simon and Donovan.
14. Esperanza Spalding, "City of Roses" (2012)
Like Viva Voce's "Rose City," Spalding's jazz-pop ode to her hometown is that rare swollen-hearted Portland love song, except the view is even, um, rosier. Over weightless keys and horns from the Pacific Crest Jazz Orchestra, the singer-bassist references a tourist brochure's worth of regional splendor, from the "rolling river" and "a mountain hooded in snow" to the hacky-sacking hippies at Saturday Market. It paints such an idyllic picture it could be sung by a Disney heroine, but it helped expand Spalding's national profile and won her mentor, Thara Memory—an old-school hardass closer to Whiplash than Frozen—a Grammy for the arrangement.
15. M. Ward, "Paul's Song" (2005)
No one would mistake M. Ward's froggy murmur for Tony Bennett, but he did write our "(I Left My Heart) In San Francisco." On this rain- and pedal steel-slicked ballad, the "Him" to Zooey Deschanel's "She" can hardly bring himself to interact with the waitresses and hotel concierges he meets on tour, so gaping the hole in his chest-cavity. Then again, they all ask him questions like, "Are you down with the latest trends?" so maybe it's just a convenient excuse.
16. Luck-One, "Sounds Of My City II" (2013)
Updating "Portland Life" for the Portlandia era, the city's most charismatic truth-teller (who's since reverted to his given name, Hanif, and decamped to New York) puts a spotlight on the places "the cameras never visited" and, as he is wont to do, tells some hard truths—namely, that this quirky bastion of liberalism treats its minority population "like we're criminals, scandalous individuals." When the cops shut down his show with Illmaculate at the Blue Monk last year, the police report cited "multiple derogatory lyrics toward the police" and misquoted the chorus, only proving his point.
17. Dead Kennedys, "Night of the Living Rednecks" (1979)
OK, so it's not so much a "song" as a stage rant set to faux-jazzbo noodling, but it stands as a half-hilarious, half-frightening testimonial to Portland's backwater days, where keeping it weird could get you doused with water and called "faggot" on a public street. Onstage at OG punk club the Earth, singer Jello Biafra kills time by recounting his last trip to town, when he got chased into a phone booth on Burnside by a mob of club-wielding jocks and mocked by onlookers. "And I thought, 'So, this is Oregon,'" he sneers with trademarked sarcasm. "'Tolerant Oregon!'"
18. White Glove, "Division Street" (2014)
At once a sincere lament for the gentrified Southeast and a tongue-in-cheek homage to the institutions being replaced (fancy restaurants instead of meth labs? Baby strollers instead of weed dealers? Noooooooo!), "Division Street" encapsulates the current Portland moment with only a few chords, a dinky keyboard riff and a catchy-ass melody. Whenever the "Save the Oregon Theater" campaign starts, this will undoubtedly serve as its anthem.
19. Dan Reed, "Bust a Bucket" (1990)
Every city needs its novelty jock jam, and "Bust a Bucket" is Portlandâs "Super Bowl Shuffle." Whacked in the head with a basketball while sitting courtside at a Blazers game, local cheese-rock idol Dan Reed proceeds to earnestly sing-rap a concussed daydream about getting pulled onto the court by Rick Adelman, chatting up Ahmad Rashad and draining hook shots from half-court, while Jerome Kersey, Terry Porter and the rest of the early '90s squad chant the supercalifragilistic chorus. It's aged like a pair of Zubaz, but mention "Bust a Bucket" to any longtime 'zers fan and watch their eyes well up with nostalgia.
20. Tom Waits, "Pasties and a G-String (at the Two O'Clock Club)" (1976)
Go home, Tom, you're drunk. Ogling "Portland through a shot glass," and with probably only one eye still open, Waits, sounding even more belligerent than usual, practically has a stroke at the sight of Stumptown's famous live nude girls, scatting nonsense and growling about getting "harder than Chinese algebrassieres," as va-va-voom drums evoke images of undulating flesh. As the Two O'Clock never existed, debates persist about what actual club that got him all hot and blubbering—the popular guess is Mary's—but the song is really a self-fulfilling prophecy: Go into any strip joint in Portland now, and you're more likely to hear Tom Waits than Juicy J.
21. Jason from L.A. (a.k.a. Fred Armisen), "The Dream of the '90s" (2011)