The Last of the Sad Bastards

10 years after his death, Elliott Smith is still estranged from Portland.

Elliott Smith sang it himself: Pictures of him are always wrong.

So the photo of him at Disneyland, taken in 1996, must be Photoshopped, right? The saddest songwriter in the world—a man who committed suicide by stabbing himself in the heart a decade ago next week—at the happiest place on Earth, a smile cracked across his 20-something face. It doesn't make sense.

And yet, there's more images like this, hung on the walls of Union/Pine as part of a one-night show last week called Elliott Smith: The Portland Years. Smith in a fur jacket, pursing his lips and posing as if he were a glam-rocker. Smith in fur pants and a devil mask threatening the camera with a plastic pitchfork.

In his music, Smith was the eternal sufferer. The New York Timesobituary published after his death in 2003 called him "a luminary of independent rock" who wrote "bleak stories of turmoil, addiction, domestic violence and despair."

In person, though, he was a goofy drunk with an absurd sense of humor, who beat jokes into the ground like a kindergartner. That's how Portlanders—the people who knew Smith best—describe him. 

Though Smith's best-selling record, 1998's XO, sold only 400,000 copies, he is, to many critics, the best songwriter ever to emerge from this city. His influence still resonates. A few years ago, Paste magazine ranked Smith the very best thing about Portland—above Powell's, Mount Hood, the book Geek Love and Gus Van Sant's entire oeuvre. Last month, Madonna filmed a performance of his song "Between the Bars." A new biography, Torment Saint, is out this month (see review), and a second documentary film about Smith is in the works.

Before Portlandia branded our city, Elliott Smith did the same—except his Portland was about self-loathing, set among the cracked sidewalks of Alameda. He told stories about addicts getting off the bus at Southeast Powell Boulevard and 6th Avenue to cop, and chronicled the absurd ritual of the Rose Parade, with its "ridiculous marching band" playing "some half-hearted victory song."

Today, local bands like the Decemberists sing about dirigibles, shipyards and CIA operative Valerie Plame, while Menomena mounts ironic album-release parties set to Pink Floyd laser shows at OMSI. These bands tend toward the conceptual, not the personal. And those bands emerged around 2003, the same year Smith died and Voodoo Doughnut opened. It was the end of gloomy, earnest Old Portland and the birth of whimsical New Portland, the "youth magnet city" of craft beer and chickens with names.

Smith tapped into the same existential gloom explored in the '80s by the Wipers' Greg Sage, who once described Portland as "Doomtown." It wasn't obvious back in 2003, but it's clear now: Elliott Smith was the last man living in Doomtown.

Smith released his debut solo album, Roman Candle, in 1994. At the time, the Portland rock scene was emerging. Grunge had broken big in Seattle just three years earlier, showcasing the Pacific Northwest to the mainstream music industry. A&R men were taking Portland punk bands to dinner and dangling record offers that never materialized. The enticement of fame—or, at least, of the chance to quit working day jobs—had drawn a glut of loud rock bands set on riding the Seattle wave.

And Smith, initially, was part of that wave.

At Hampshire College in Amherst, Mass., Smith formed Heatmiser with Neil Gust and brought the band back to Portland in the early '90s. Heatmiser released three albums of Fugazi-indebted post-punk, developed a fervent local following and signed a deal with Virgin Records. But Smith never totally fit in. Eventually, he went on his own.

"Once he started recording his solo stuff, that was so much quieter, he realized his voice was much better suited to music that was less aggressive and had more space in it," says Heatmiser drummer Tony Lash. Later, Smith would credit his time in the band with teaching him "a lot of things I don't want to do musically."

Roman Candle, released on upstart Portland label Cavity Search in July 1994, was, in contrast to Heatmiser's roaring sound, almost invasively intimate. Recorded at his girlfriend's house at Southeast Taylor Street and 29th Avenue, it featured little more than acoustic guitar and Smith's barely-there voice. Listening now, it's as if you have an ear cupped against the basement door.

The album caught people by surprise: Jackpot Recording Studio owner Larry Crane, who'd go on to oversee several Smith recording sessions and serve as his archivist, had written off Smith for his involvement in Heatmiser, which he lumped in with the "loud, stupid guitar bands" he was tiring of. Crane's opinion changed after hearing Roman Candle.

"I'd been listening to a lot of Nick Drake and Tim Hardin," he says, "and I was like, 'Fuck, that's right in there.'"

Roman Candle and the two indie records that followed—Elliott Smith and his breakthrough, Either/Or—became talismans for Portland's basement-dwelling creative class, "cheat sheets for comprehending every Rose City songwriter who ever wrestled with a four-track recorder in his or her bedroom," as John Graham wrote in WW after Smith's death. Smith's contemporaries, like Hazel's Pete Krebs and Crackerbash's Sean Croghan, joined him in exploring their softer, folkier sides. None of them could do it nearly as well.

Today, it can be hard to place Smith. When Mark Baumgarten, WW's former music editor who is now the editor of Seattle Weekly, moved to Portland from Minneapolis in the summer of 2003, he says he expected to interview a bunch of "up-and-coming sad bastards." Instead, he found a scene whose energy had returned to the loud rock bands that Smith's whispered melancholia had supposedly replaced. From an outsider's perspective, his albums cast such a long shadow over Portland that they distorted reality.

"His music was an anomaly in some sense," Baumgarten says. "Though he, as a person, is really connected to that community, aesthetically, I don't know if his music fits at all."

No one, it turned out, sounded like Elliott Smith. They'd all given up trying.

The moment Sean Croghan knew Elliott Smith was bigger than Portland happened in Los Angeles during a two-week tour in the mid-'90s. He, Smith and four other Rose City rockers-turned-singer-songwriters, eager to try out their new acoustic guises on the road, crammed into a van and headed down the coast. At the time, the name "Elliott Smith" meant little outside Portland. Neither did "Sean Croghan," but because his vigorous touring fronting seminal Portland rockers Crackerbash earned him nominal recognition, he became the tour's de facto headliner.

Smith quickly emerged as the act no one wanted to follow. Whatever his failings as a rock frontman, with the volume dialed down, they transformed into strengths. His gentle wisp of a voice, often strained in Heatmiser, could absorb an entire room into his hushed orbit. And he often did so after vomiting from nervousness backstage.

By the time the tour reached L.A., Smith had taken the closing slot. The show, at a bar whose name Croghan can't remember, was filled with record-industry people and friends of industry people, perhaps the worst possible audience for unknown singer-songwriters from the Pacific Northwest.

"All night long, people had been polite, having their conversations, doing what you do at a bar and enjoying themselves," says Croghan, who lived with Smith for a time. "So there was a fair amount of chatter throughout all the sets. And Elliott got up there and started performing, and you could just watch the room get sucked up in what he was doing. One by one, people just stopped, and everyone's attention was focused on the stage. It became obvious to me that this guy is so much more amazing than the rest of us on this tour."

Why was Smith the most successful songwriter in his peer group? Some cite the tangibles (finesse as a guitarist, a gift for melody and arrangement), others the intangible ("aura") or the dumb luck of the music industry. Ultimately, though, consensus opinion mirrors Croghan's revelation: Smith was just better than everyone else.

"He's this entire package you don't often see," says William Todd Schultz, author of Torment Saint: The Life of Elliott Smith. "He really knew what he wanted in a song, and he worked at it so hard and wrote so many songs and recorded at a young age that he was making stuff effortlessly that was incredibly accomplished."

"Ambition" isn't a word commonly associated with Smith—who dressed as shabbily as any part-time record-store clerk in town—yet in conversations with those who knew him, it comes up frequently, extending all the way back to Stranger Than Fiction, the ornate prog-pop recording project he and Lash formed along with two other friends from their Lincoln High School band class. Smith seemingly never stopped playing: Croghan often came home to find him on the couch, working on songs while watching Spanish television with the volume low.

"He wanted to write songs and he wanted to record songs," Crane says. "Everything else was an obligation to get to those two." In 1995, Smith secured a publishing deal—something few Portland musicians could claim —allowing him to quit his drywall job and focus all his time on songwriting. "As soon as he did," Crane says, "I know, as his archivist, there were a whole lot more reels of music being recorded, and much more songs  being written.”

Smith's relentless drive to create was, perhaps, indicative of just how many demons he had to exorcise. (Much of his depression, it's believed, stemmed from the revelation that, during his childhood in Texas, he'd been sexually abused by his stepfather.) But the more he honed his craft and the more listeners connected to his agony, the more obligations were foisted upon him.

After the success of 1997's Either/Or, Smith was something approaching a celebrity in Portland. He'd lost the comfort of relative anonymity. He tried relocating to New York first, but found it didn't give him the isolation he desired. In L.A., he could disappear into the sprawl. He rarely spoke to the people who kept him grounded back in Portland.

Crane views Smith's famous performance at the 1998 Academy Awards, shoved awkwardly between the Best Original Song performances of Trisha Yearwood and eventual winner Celine Dion, not as the pinnacle of his career but the start of his descent. He was basically forced into doing it: The show's producers threatened to hire a replacement to perform "Miss Misery" if Smith backed out.

"My feeling watching him up there was, I wish he had a way he didn't have to do that," Crane says. "At the time, even. I didn't say that to many people because they think you're crazy, because you're supposed to take every opportunity and all those things. In a way, that got him a lot of publicity and a lot of notice and prepped the stage for XO to sell a decent amount of records, but it would've been so nice if it hadn't happened. It's like if Nirvana hadn't written "Smells Like Teen Spirit." Kurt [Cobain] might still be around."

Smith played Portland for the final time on Dec. 20, 2001, at Crystal Ballroom. It was, by all accounts, a disaster. He flubbed guitar parts. He forgot lyrics. He looked disheveled—more than usual. His between-song banter ("I'm gonna get it together," he promised during one interminable break, "I just got to think of a song") resonated as a cry for help.

It wasn't an isolated incident. The shows in the last years of Smith's life were marred by a lack of control: leaving songs half-finished, relying on the audience to sing his lyrics back at him. It was indicative of his life offstage since leaving Portland in 1997, marked by what Schultz calls a "galloping, intense paranoia," brought on by a cocktail of heroin, alcohol, crack cocaine and psychiatric meds fogging his system.

"From about 2000 to the end of his life, part of his personality had been taken out," Schultz says. "That's the way a lot of people described him. Pete Krebs said he was like a zombie. He was unreachably screwed up."

At that point, Smith's friends in Portland had lost track of him, but even from afar, it was clear he wasn't well.

"When I heard Figure 8, I remember feeling kind of sad," Lash, his former Heatmiser drummer, says of Smith's last album, released by DreamWorks Records. "I wasn't around him, and I don't know the degree or what substances might have been involved in his life, but at least to my ear, there was an emotional remove to it that made me feel sad. He wasn't as emotionally plugged into the music. It seemed more like an exercise in good chord changes and good notes and good words, but there was something missing from the previous records, which is that feeling of him sitting right there, communicating that emotion directly."

"He got caught up in a bunch of different dilemmas," says Christopher Cooper, co-founder of Cavity Search Records, whose last memory of Smith is an equally alarming Seattle show he played the night before the Crystal. "One was his past. One was his career. And the other was his addiction. Different places symbolize different things to Elliott. I think that the addict always knows where home is and always knows where clean is, but the addict doesn't always want to go home."

If you believe certain message boards, the facts of what happened on Oct. 21, 2003, are hardly "facts." But according to the only other person who was there, Smith's L.A. girlfriend, Jennifer Chiba, she came out of the bathroom following an argument to find Smith with a kitchen knife sticking from his chest. There was a message scrawled on a Post-it note: "I'm so sorry."

In the years afterward, the feeling, among a certain contingent, was that Los Angeles had killed Smith. If anything, though, he had gone there to die. He spoke often of suicide long before he arrived in California; being close friends with Smith meant having to spend some nights talking him down from the proverbial ledge. In L.A., he surrounded himself with, in the words of poet Nelson Gary in Torment Saint, "sycophant banditos," eager to keep him high in exchange for favors. He put hundreds of miles, geographically and spiritually, between himself and Portland, which, in retrospect, seems part of his deliberate, gradual self-immolation.

He'd become subsumed by his musical persona: the eternal sufferer, "Mr. Misery." And, in a way, his death was one final act of artistic grandiloquence.

"I have plenty of friends who are equally as sad as Elliott," Croghan says. "But I think Elliott did everything on a grander scale than the rest of us. He was a better musician than the rest of us. He was a better writer than most of us. So his depression sort of outshined the rest of our depression, too. He was good at everything he did."

In Portland, Elliott Smith remains an open wound.

Many people—including Smith's good friend Krebs and his father, Dr. Gary Smith, who still runs a psychiatry practice in town—declined to be interviewed for this story. Part of it is lingering sadness, and part of it is fatigue: A decade later, the world remains fascinated by Elliott Smith. It wants to understand him. That means returning to Portland—a very different Portland than Smith knew, except for the gray skies and slow river—to converse with the people who knew him best. And some have grown tired of talking.

Those still willing to speak, though, know why they do. In part, it's to keep his memory alive.

"That's the important thing about Elliott: the amazing songs he left behind," Croghan says. "The best songs can be played by any great musician and still sound amazing. There are some songs that it takes that personality to sell them, but I think Elliott's songs are the kind of songs that can be played by musicians 100 years from now, and people will hear the beauty, hear the complexity, hear the poetry, and it's still going to resonate, where there are many songs that won't last.

"So maybe that's why I like to talk about him. That's what I got out of him more than anything else: what an amazing artist he was. He was an amazing artist in a town full of people who played in bands.”

WWeek 2015

Willamette Week’s reporting has concrete impacts that change laws, force action from civic leaders, and drive compromised politicians from public office. Support WW's journalism today.