In February 1998, Elliott Smith was in Los Angeles, working on his next album, and living out of a hotel, when he was nominated for an Oscar. Later he described the early‑morning call from his manager, Margaret Mittleman, and his bleary response. He thought someone had died. “You’ve been nominated,” she said. “For what?” he asked.
Smith was 28, an indie singer-songwriter who had already developed a devoted following and, mostly by chance, wound up contributing to the soundtrack of Good Will Hunting, Matt Damon and Ben Affleck’s breakout film. (Director Gus Van Sant had fallen in love with his music after a friend mailed a few records from Portland, Oregon, which both artists called home.) Late in the process, Smith was asked to contribute an original song. What he offered was the dark, intimate “Miss Misery,” the song that would transform and define the rest of his life.
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In interviews, Smith would dismiss the Oscar nomination as “a freakish accident”—something he went along with only because it made his friends happy, because it made his mother proud. “For all those years, she’d been faced with her friends going, ‘Well, my son’s a lawyer,’ or ‘a businessman,’ or some occupation that has a name,” he said. “Then, all of a sudden, she could say: ‘Did you see the Academy Awards?’ ” It was like a joke to him at first; when “Miss Misery” started playing on the radio, his friend Larry Crane remembers, he ran out with Smith to his rental car in the Sunset Sound lot to listen. They thought it was hilarious.
When Smith’s friend Marc Swanson called to congratulate him, Smith sounded dismissive. “I don’t mean to sound like he was unappreciative, but I think he was a little embarrassed in a certain way,” Swanson says. “Like, ‘I’m not the kind of guy who gets nominated for an Academy Award.’ But they campaign like it’s an election. I remember him telling me that it might happen because they were trying to make it happen.”
To some extent, this was true. Years before he became infamous for far more repugnant practices, Harvey Weinstein was once referred to by the New York Times as “the Sun Tzu of Oscar warfare.” He invented the modern awards campaign in the late 1980s with his brother, Bob, and brought a special brutality to it. Marketing veteran Terry Press described the Miramax style of campaigning—with its phone banks of young assistants calling voters at home, mass‑mailed VHS screeners, and constant publicity through awards season—as “a blood sport.” The studio had an unbroken run of Best Picture nominations, from 1992’s The Crying Game to 2002’s Chicago. Good Will Hunting was part of that run. Weinstein fought hard for nominations in every possible category, ultimately getting nine, including Smith’s. It was Weinstein who had pushed for an original song in the first place. They were “secretly hoping that there was some way outside chance that they could add another nomination to the ones they thought they were going to get anyway,” as Smith put it later.
At the same time, Smith’s friends and family remember that he seemed to take a real joy in the proceedings. His sister Ashley remembers him explaining that he wanted to wear a white sport coat with a pink carnation for the ceremony, after the country song by Marty Robbins. “There were things about it that he made so special for himself,” his friend and publicist Dorien Garry says. His A&R exec at DreamWorks, Luke Wood, still remembers the phone call where he made arrangements with Prada. When Ross Harris shot the “Miss Misery” video a few days after the nomination was announced, Smith showed up on set in his white suit, beaming. “I was so happy for him,” Harris says.
“As soon as he was nominated, he called me right away,” Smith’s longtime girlfriend Joanna Bolme says. “Do you want to go to the Oscars with me?” he asked. She can’t remember whether they were together at the time, but it never felt like a surprise. “It wasn’t like, ‘Oh, that’s so great that he asked me,’ ” she says. “It was like, ‘No, of course he asked me. Of course I’m the one that’s going.’ ” “We talked a lot about it, obviously,” his sister Rachel told me. “I remember him getting really excited about his white suit and Joanna being really excited about her dress. It was like, ‘If I’m going to do this thing, I’m going to do it. I’m going to wear an outfit I’ll never, ever be able to wear under any other circumstances anywhere.’ ” Sometimes he described it as a tribute to John Lennon.
Part of the joy of watching Smith respond to interviewers, before and after the Oscars, is something like the joy of the white suit. The way he talked about the nomination, about the show, makes you feel how acutely absurd the whole thing was, the world he had found himself in.
“Supposedly, if you’re nominated, then people who make clothes sometimes want you to wear their clothes,” Smith said.
“It was like I was playing a really weird show that consisted of one song,” he said.
How much is the Academy Awards about music, anyway? a reporter asked him.
“None,” Smith said. “But how much is it about movies?”
“Seeing celebrity through the eyes of somebody like him, you see how ridiculous it all is,” Rachel says. “He shows it to you. That’s one thing people love about Kurt Cobain too. He was really good at showing people, Look, this is nuts. But also, I think people in that position often do end up really suffering because they end up feeling like they’re shouting into a void. Because they’re like, ‘This is nothing!’ And people are like, ‘You’re amazing!’ And they’re like, ‘This is nothing!’ And people are like, ‘You’re amazing!’ ”
Everything means nothing to me, I say.
“How much is the Academy Awards about music, anyway?” a reporter asked Elliott Smith. “None,” he said. “But how much is it about movies?”
“There you go,” she says.
Harris made the “Miss Misery” video because he had bumped into Smith in Los Angeles. “He was like, ‘Hey, I have to do another music video. I know they’re a hassle, but do you mind doing it?’ ” Harris says. “And it was like someone was asking you to help them move a couch. That was his same tone of voice. So I go, ‘Well, what’s it for?’ And he’s like, ‘Oh, they put my song in some movie.’ ”
Harris didn’t want to put shots from the movie in the video, whose plotline revolves around Smith being tailed by a traffic cop who happened to be on set. At first, he thought he wouldn’t have to. “It never makes any sense,” he says. “Like, this is a beautiful song that Elliott wrote, then also now Matt Damon and Robin Williams are hugging? I don’t get it. I mean, I told them, ‘It seems like it’s gonna be homoerotic to me. And I’m not against that, but …’ ”
In the end, Harris says, “they just stuck it all in there anyway. I don’t know how much of that relates to Elliott. But my main point is, these people did not want me to make that video. They wanted a big‑time director to make that video. And Elliott was like, ‘No, my friend Ross that made my other videos is gonna make it.’ And he didn’t have to do that. Believe me, no one wanted him to do that.” At the end of the video, Smith stuffs quarters into someone’s parking meter, which one of his friends described to me as a metaphor for what Smith always tried to do with the people he loved. “He was very much like, ‘I’m getting this opportunity. I want to give that opportunity to them too,’ ” Harris says.
Smith was in the room when Harris finished the edit. “What do you think?” Harris asked, and Smith pointed out a shot where the camera came in close while he stood in the doorway. It was too close, he said nervously. It wasn’t flattering. “Elliott, you’re such a hunk,” Harris told him. “You got to get over it, man. You’re a really fucking good‑looking dude.”
I’m really glad you said that to him, I say, because I know he felt sensitive about the way he looked, and I think he was beautiful.
“I felt the same way,” Harris says. “I was like, ‘I’ll take it out if you’re really against it, but I just got to tell you, like, you’re a hunk. You just got to accept that you’re just a fucking good‑looking dude.’ And he just laughed and was like, ‘OK, you can leave it in.’ ”
The pageantry around the nomination, the flood of press attention, was battering for Smith. “Oh my God, everything’s going nuts over here,” Garry told the drummer Bob Bert when he called to set up an interview for his zine, BB Gun. He joked that Smith had turned down Regis and Kathie Lee, which wasn’t true, but it wasn’t much of a stretch.
Before the Oscars, Smith had been coping uncomfortably with fame, enough that he could sing on Either/Or about perceptions of him that were “completely wrong,” but it was nothing compared to this. “All of a sudden, he had to do interviews for Us and People and all these magazines that wouldn’t have touched him,” Mittleman said later. “We were trying to focus on recording XO, but my memory of that time is all about just getting him to sit down in the lounge of Sunset Sound to do interviews.” He went on Late Night With Conan O’Brien. He talked to a painfully uninterested Carson Daly. When he spoke with Bert for his zine, or when his friend Barbara Rushkoff interviewed him for People, he expressed relief just to be talking with a normal person. “He was like, ‘It’s so funny, my mother will finally think I made it now because I’m in People,’ ” Rushkoff says, laughing.
He was seen holding hands with Minnie Driver, and then everyone wanted to know if they were dating. “It didn’t make my girlfriend really happy,” he said. In his interview for BB Gun, Smith mentioned Bolme, and Bert said, “I thought you were fathering Minnie Driver’s child.” Smith snorted. “It wasn’t like that at all,” he said.
They did spend time together. “Whenever I think of Minnie Driver, it just cracks me up, because I remember Smith having a conversation with me in which he said he felt like Sonny Bono next to Cher,” his sister Ashley says. “Like, a little bit self‑conscious about his height and stature.” Their romantic involvement is less of a tabloid invention than Smith made it seem; the musician Mary Lou Lord thought they were dating, and told people as much. Years after Smith died, Driver recorded a cover of “Waltz #2.”
More than anything, people kept asking Smith about being discovered by Gus Van Sant while playing in a coffeehouse. “Which, you know, we used to laugh about because obviously Elliott was doing very well,” Swanson says. Crane remembers hearing Smith explain repeatedly in phone interviews that he had six albums out already. “People want this other story,” he says. “They want the rags to riches or the overnight success. It’s just these stupid stories that people want to hear played out over and over.” It happened often enough that Swanson made a plaster sculpture called Rescued From Obscurity. “They said during the press for Good Will Hunting that Van Sant had rescued Elliott from obscurity,” he says. “And so this was a comment on that.” He shows it to me in his studio: a python wrapped around a squirrel, strangling it.
Garry quit her job as Smith’s publicist not long after the nomination. “I didn’t quit because of Elliott,” she says, but it felt good, in the end, not to be part of the thing that was crushing him. “It really was like … he was right,” she says. “Everybody was so stupid.” She laughs. “They’re projecting all of this on him, and he can get through an interview and be cordial and patient, answer stupid questions. But then afterward he’d just be fucked up from it, you know? And it was like, ‘At what cost?’ ”
“Not to bring up any personal things or anything,” Bert said, interviewing Smith before the Oscars, “but it’s like, just last year you canceled a bunch of shows due to your personal demons and everything. Is it going to be a real drag? I mean, after this all happens, you know? Because you’re going to be, like, recognized everywhere. You think it’s going to drive you crazy, or …?”
“I don’t think I’m going to be recognized everywhere,” Smith said. “I mean, the Academy Awards are going to be over in a month, you know?”
“Yeah.”
“And then—and then I’ll be back to normal.”
But nothing was ever normal again. He had lost his anonymity, his ability to walk absently through the streets or write quietly in bars, undisturbed. It took something from him. He couldn’t be alone anymore, not even in his head. He was used to that world being “unpeopled,” he said later, “and for a while there were lots of people camping out in there.” “I didn’t realize how petty people can be,” he said. “I didn’t realize that Entertainment Weekly would say I was a ‘sedate Beck impersonator’ because I wore a white suit.” The “Miss Misery” video was featured on MTV’s 12 Angry Viewers, and it “did my head in,” he said. He watched them tear it apart.
Those first few months of 1998 would prove to be a turning point. As Smith took calls from the Sunset Sound lounge, he was working on his major-label debut, with all the new touring and publicity demands that would come with it—repetitive interviews where journalists wanted to know if he was depressed, if his songs were about drugs, if he was on drugs. “They’re trying to pigeonhole you into this sad guy, this Tom Waits kind of bar-sad guy,” Bolme remembers warning him at one photo shoot. “Don’t let them do that to you.” But this image would prove hard for music writers to resist. For a long time, when Smith went to visit his father, he would head straight downstairs to look up his press on the computer. It had swallowed and distorted him, like a fun-house mirror.
Considering the Oscars in hindsight, he said, “That kind of derailed my train, although it took quite a while for it to fully derail.” In some ways, he felt it wasn’t back on track until the year he died.
For years after the Oscars, Smith talked about how they wouldn’t give him a chair. “The rehearsal day, they didn’t really know what to do with him, performance‑wise,” Bolme says. “He wanted to sit down like he usually does. And that just didn’t go the way they had envisioned the production to go—like, you can’t just bring out a stool.” They asked him to sit down on the steps in front. “And this was another situation I had to step in on his behalf,” she says. “I was like, ‘You can’t do that. It looks like Sesame Street.’ You know, every single person here is nominated for the same thing. Why is he not being treated with respect?”
They offered other solutions. “I would have to sit behind this moving panel during the Trisha Yearwood song,” he said, “and then it would dramatically raise up to reveal that I’d been sitting here all that time.” In the end, he agreed to stand. A reporter who was present remembers him asking, in some distress, if he could have a monitor.
The night before the Oscars, Smith stayed up until dawn, drinking with Mark Flanagan at his club Largo. He was dreading it. “You’ve fucking got to go!” Flanagan told him. “It’s going to be great! You’re going to be up there between Harry Belafonte and David Hasselhoff!”
“You’re not making it any better,” Smith said.
Smith arrived in a limo with his producer Rob Schnapf, Mittleman, and Bolme, who wore a black dress designed by Storm Tharp. Standing outside the Shrine Auditorium, Van Sant’s then boyfriend, D‑J Haanraadts, asked, “How are you feeling about this? A billion people in the world are going to see you perform.” Smith looked at him in terror. Out of guilt, Haanraadts complimented him on his suit.
At rehearsals, someone had told Smith and Bolme hopefully that they could come in through the back. “And we were like, ‘Pfft, we’re walking the red carpet,’ ” Bolme says. They were surprised by how highly choreographed it was. “Everybody’s got their team with them, and their team is jockeying to get them a good spot on the red carpet,” she says. They were stuck until Cuba Gooding Jr. offered to let them in, which seemed like a kindness until they realized it meant they were left walking behind Madonna, and then they wondered if it was a strategy. Smith followed her down the walkway, trying not to step on her white train. There’s a picture of that moment. Bolme looks lovely, with her dark eyes and dark dress, holding Smith’s hand, both of them smiling like they’re getting away with something.
Later, Smith talked about what it was like there, the surreal mundanity of it. He had a trailer across from Michael Bolton’s; he was given a gift basket that included first‑class upgrades on United. He slipped in his new Prada loafers backstage, and Robin Williams asked him for a Tic Tac. If you got up to go to the bathroom, Smith explained, a seat filler would step in, so you would come back to “some guy sitting there with your girlfriend.”
He performed sandwiched between Aaliyah, Bolton, Yearwood, and Céline Dion, who had been nominated for the powerhouse “My Heart Will Go On.” He was standing at the side of the stage, discreetly trying to scuff up his loafers so he wouldn’t slip again, when Dion asked him if he was nervous. From her seat, Bolme could see that she was being kind to him. “She was very expressive,” Bolme says, “touching him and looking at him” in a very French Canadian way.
“She was really, really sweet,” Smith said years later. “It made it impossible for me to not like Céline Dion anymore.” She hugged him, and he sounded moved still when he talked about it. “It was simply too human to be dismissed,” he said.
Then he walked onstage.
Smith’s friends Garry and Josh were watching at home, with little candles shaped like the Oscars statuette scattered around the living room. “We were also like, ‘Elliott would be so mortified if he knew we were doing this,’ ” Garry says, cracking up. “He’d much rather we be at Max Fish, ignoring it.”
“It was really a beautiful thing to see,” Josh says. “It felt like a bit of a coup or something.” People around the country felt that longing, hearts in their throats. As Slate’s own music critic Carl Wilson wrote years after, the moment of the Céline–Elliott matchup seemed to define a divide in pop music, but also promise, just for a night, that it might be overturned. “I was enough of a populist even then to dream that love might move mountains,” he wrote.
“I don’t know about you, Josh, but I had this bad feeling,” Garry says. “It was this moment of ‘Holy shit, this is unreal, that this is happening,’ then also like, ‘Oh God, is he going to survive this?’ ”
“We were cheering when we saw him perform, but … it was so ‘What’s gonna come after this?’ ”
If you watch the performance now, Smith looks like a vision onstage, an apparition, his suit a hallucinatory white. There’s a blurry sheen on him, like looking at a star. He plays his song for 90 seconds, one stanza short, his coat bunched up at the shoulders. It was like he had gone to the moon, a friend tells me. He was here in his astronaut’s suit, and he’d gone to the moon.
When I was working on this book, everyone kept asking me if I’d seen Smith “with the puppet”—a clip had surfaced from Smith’s appearance on a defunct morning show in 1995, with its scraggly puppet co-host, everyone treating Smith like a joke until the moment they shut up and let him play, and then they are completely silenced by it. And the way people asked me, with disgust or delight, drawn to the strange ludicrousness of it, made me wonder if that was how people asked back then: Did you see Elliott on the Oscars? Did you see Elliott in this world that never knew what to do with him?
I thought about what his sister Rachel said about Cobain revealing the frailty of the construction he participated in; his mere presence, with his knowing smile, dismantled it. This means nothing, he was saying. Smith made it look ridiculous. But he also stood apart and above it. There’s something so lovely about the ugly puppet stunned into silence when Smith plays “Clementine,” about the spotlight falling softly on his shoulders in the Shrine as he peers out at the audience of celebrities from behind his bangs. This means nothing, he said, and his somethingness felt so overwhelming in comparison.
“He was never under any sort of illusion that he could win,” Rachel says. “When they opened the envelope, for just a split second, I thought, Oh, what if …? But then of course it was Céline Dion.”
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At the Miramax after‑party, Smith got drunk and talked to Stewart Copeland and got drunker. “I was at least three sheets to the wind by then,” he told Bob Bert. “I just piled it on. Whiskey and more whiskey and more whiskey.” He said he wanted to forget who he was.
“During the song, it was fine, because I was inside the song,” he said later. “I was inside the song till it was over, and then it’s like I wake up, and then the crowd is there.” But when he saw himself on video, he was “appalled.” “It bummed me out,” he said. “I looked so fucking fragile.” People kept telling him as much. “All this focus on this one two‑minute performance in a suit,” he said. “Which made me feel like I was in church, or maybe at a funeral.”
He talked about the way Dion commanded the stage, how he was dismissed for not commanding it himself. But he wasn’t trying to, he said. “That’s part of what her kind of performance is,” he explained. “My kind of performance is more based on staying inside some construction that I’m showing.” When he watched himself on tape, he could see how fragile the construction was.
What was the construction? How could he not have known what it looked like, the house he had made?
From Nobody Broke Your Heart: An Intimate Biography of Elliott Smith, by Jamie Fisher, published on Aug. 25, 2026, by Dutton, an imprint of Penguin Publishing Group, a division of Penguin Random House LLC. Copyright © 2026 by Jamie Fisher.