This cover story originally appeared in the February 2000 issue of SPIN. We’ve digitized it in honor of When the Pawn…‘s 20th anniversary.

The scent of corned beef wafts through the air. LeAnn Rimes and Elton John croon softly in the background. A surly host downstairs, dark wood tables, bowls of pickles. No, this isn’t some dank New York City sandwich joint. It’s the Greengrass Deli in sunny Los Angeles—the last place you’d expect to find Fiona Apple, outspoken vegan and animal-rights activist. But despite spending many of her childhood years in L.A. and the past few years as a full-time resident, the New York transplant doesn’t drive. Which makes it really hard to figure out where to sit down and do an interview.

She’d been dropped off at my hotel by a friend and shuffled through the lobby alone. No handler, no entourage, not even a cell phone (later she’ll have to find a payphone to call her boyfriend, Boogie Nights writer/director Paul Thomas Anderson, to pick her up). Her hair loose and messy, her face free of makeup, Apple had no strategic, publicist-stoked ideas for a destination to make her look cool, or even just one where she’d feel comfortable. So after a bit of aimless wandering around West Hollywood, Greengrass Deli it is. Just about the only thing Apple can order is an iced tea.

“Really, like, I never know where I am” she says. “I can’t get around by myself. I have a bit of anxiety about learning to drive. I just feel like I’d get really angry or I’d be so nervous of fucking causing an accident that I’d actually cause one. I know it’s annoying for my friends, but it doesn’t bother me.”

Apple doesn’t let any of that anxiety, anger, or nerves get in the way of her singing and songwriting. In fact, all of those emotions figure prominently on the wiry 22-year-old’s stunning new album, titled (as you probably know from the endless mocking it has provoked) When the Pawn Hits the Conflicts He Thinks Like a King/What He Knows Throws the Blows When He Goes to the Fight/And He’ll Win This Whole Thing ‘Fore He Enters the Ring/There’s No Body to Batter When Your Mind Is Your Might/So When You Go Solo, You Hold Your Own Hand/And Remember That Depth Is the Greatest of Heights/And if You Know Where You Stand, Then You Know Where to Land/And if You Fall It Won’t Matter, Cuz You’ll Know That You’re Right.

More on that title later; for now, let’s just say that the music inside the packaging not only delivers on the promise of her soulful, triple-platinum 1996 debut, Tidal, it exceeds all expectations. As mature and realized as the first album was, When the Pawn… is richer, more focused and—thanks largely to producer/L.A. underground hero Jon Brion—more textured. Its strengths reveal not just an older and more experienced writer but also a newfound confidence in the studio, which Apple credits largely to Anderson, 30, her boyfriend of two years. (Anderson’s new film, Magnolia, coincidentally opened a few weeks after Apple’s album was released, which will probably lead to their anointing as Young Celebrity Couple of the Moment. “The timing is so ridiculous,” he says. “I’d want to slap us.”)

Of course, the first round of the Fiona Apple phenomenon encompassed more than her songs. The lo-fi, jailbait-porn vibe of the video for her hit single “Criminal,” her infamous “This world is bullshit” speech at the 1997 MTV Video Music Awards, and her sometimes-loopy interviews—often interrupted by bouts of crying—became inextricably linked to her work. Only 17 when sessions for Tidal began, Apple was embraced and reviled, attacked and defended, with equal passion.

Just the idea of a talented young woman acting so unpredictably, unafraid to seem crazy or pompous or tortured or ambitious, seemed to freak out many people. Her poetic, highly dramatic lyrics (“You’ll never feel the heat of this soul / My fever burns me deeper than I’ve ever shown”) made her the voice of a new generation of doomy, Sylvia Plath-loving high school girls, spawning online Apple bulletin boards full of posts like “I really believe that [Tidal] saved my life!” But others found a sexy, waiflike major-label recording star protesting the superficiality of the world a bit much to swallow—Apple recently told MTV that the biggest misperception about her is that she’s a “sad brat with no sense of humor.” For fans and foes alike, the contrast between such advanced tracks as the snarling “Sleep to Dream’ or the melancholy, longing “Shadowboxer”—songs that placed Apple squarely in the tradition of such groundbreaking, piano-playing women as Nina Simone and Laura Nyro—and the adolescent fumblings of her public life quickly made her rock’s most fascinating high-wire work-in-progress. “I love her I-don’t-give-a-fuck attitude,” says Missy “Misdemeanor” Elliott.

These days, Apple comes across far more low-key than her history might indicate. She’s quick to get riled up but equally as quick to laugh, especially at herself. For a woman who spends half her album warning away friends and lovers because she’s “crazy” or “a mess,” explaining that “it’s hard enough even trying to be civil to myself,” Apple seems quite self-assured and composed in conversation (though she manages to work the word fuck into seemingly every other sentence). And after feeling burned by her presentation in the media last time out—and realizing that she was in some ways complicit in it—her primary obsession is doing things, in her music and her life, exactly the way she wants.

For better or worse, the complicated Apple stands in marked contrast to her young pop contemporaries, a point that’s not lost on her. “Okay, there’s obviously a lot that bugs me about pop music,” she says in typical rapid-fire, paragraph-long style. “But it doesn’t bug me because I don’t like it, you know? What bugs me the most is that it means a lot to me that I write my songs. And people who don’t write their songs better be fucking really great performers and really have a fucking voice. Otherwise, why are you there?

“I’m not [picking on] Christina Aguilera, because it seems like she can sing, but I was reading that the people who wrote her ‘Genie in a Bottle’ song said something to the effect of, ‘It was really great she could sing. We didn’t have to use any pitch control.’ And it makes me feel like, okay, if this is credit that she’s gotten for not having to use pitch control, then I want fucking extra, extra, extra credit! But not only do I not get extra credit for writing things, it’s not even something that anyone’s interested in.”

Apple later calls to make it clear that she’s in no way dissing Aguilera with these remarks—”the last thing I want to do is to say something that’s going to hurt anyone.” (Not surprisingly, she’s big on follow-up calls, leaving messages at my home because “it’s not really polite” to interrupt me at work.) But there’s no question that it will be a challenge fitting Apple’s layered emotions (let’s hear ‘N Sync pull off a line like “It’s true I do imbue my blue unto myself / I make it bitter”) and sophisticated jazz harmonies into a pop/rock world dominated by immediate gratification—whether the teen-sap of Britney on one side or the dull crunch of Limp Bizkit on the other.

The first time around, Apple was able to ride the tail-winds of the mid-’90s Alanis-and-Lilith “Women in Rock” moment; now, she’s released an album when female rockers are practically invisible. “It feels like there’s a backlash against a genre she was never a part of,” says Andy Slater, who became Fiona’s manager after hearing the then-teenager’s four-song demo tape at a Christmas party. “It’s just a gender she’s a part of.” (After a surprisingly strong debut for When the Pawn…, which sold more than 100,000 copies in its first week of release, radio interest finally picked up for the skittery “Fast as You Can.”)

We leave the deli and walk across Sunset Boulevard to the Virgin Megastore. As Apple pulls her jean jacket and fraying green sweater tighter around her small frame, she says that she hasn’t been listening to any music at all lately, old or new. In the music-video department, she looks wide-eyed at a sea of unfamiliar faces, picks up a Christian-rock compilation and hastily puts it down when she figures out what it is. She points to a Ricky Martin video. “Now, he can perform,” she says. “And he probably doesn’t need a pitch shifter. I’m okay with him.”

The ripple of energy that comes from spotting a rock star passes through the store as we walk downstairs: kids whisper and steal glances. One trembling teen approaches her, seemingly on the verge of tears. He begs for a hug and an autograph, then asks Apple to write “something inspirational.” She giggles and declines—too much pressure to be deep on demand. But she takes his address and promises she’ll mail something to him later. “I heard about the album title being really long,” he sputters, “and then when I first read it I didn’t understand it. But the second time I read it, it really touched me.” Then he asks innocently, “Why do you think so many people hate you?”

At the counter, the clerk only has one question, and it’s a practical one. “Where’d you get that title?” he asks, shaking his head. “We saw it in the catalog and said, ‘How’s that going to fit on the spine?'” Exiting the store, Apple sighs. “How much do I wish I could backpedal on this title now?”

***

OKAY, SO ABOUT THAT TITLE. NOT SINCE PRINCE CHANGED HIS NAME to a symbol has an artist been so ridiculed for a quirky creative decision. The 90-word poem is something that Apple began reciting onstage during the Tidal tour. She wrote the slightly awkward, self-motivational message as a response to what she felt was unfair coverage of her in the press—specifically to a November 1997 cover story in the magazine you’re reading now, in which she was quoted saying things like “I’m underwater most of the time, and music is like a tube to the surface I can breathe through” and “I’m going to cut another album, and I’m going to do good things, help people, and then I’m going to die.”

“That was just the worst,” she says sharply, still visibly angry. “Because the things that are in there, I did say. But I don’t think it’s enough to say, ‘Well, I said those things, and I should have known that it was going to come up.’ I just felt set up, that the angle was already decided, like, ‘We know at some point she’s going to say some crazy stuff.’

“I read lots of articles where the person comes off fine,” she continues, “And I’ll go. ‘Oh, I like that person.’ And then I’ll read the story again and think of the ways that I could make the person look awful with the same things I’m given. It makes me want to get up on stage and start ranting—’People, don’t listen, it’s all bullshit in the press’—which I’m smart enough now not to do.”

She wrote the When the Pawn… poem on her tour bus immediately after reading the negative letters to the editor that ran in response to the Spin story. But only later did she decide to make it the album title. “The reasons why I did it were just stupid, really,” she says with more than a hint of exasperation. “I’d had this idea that I was going to use my California ID picture for my cover, with mainly words around it. It would be like a ‘fuck you’ to having to have a picture, because on the last album I liked the photos, but then when I saw the finished CD, I had been totally airbrushed. I just hated that, how it looked all slick. So what’s behind this is, you guys don’t get that this time. You don’t get me sitting there trying to look pretty, you don’t get that extra push.”

Apple has since thought of a simpler title that she thinks would have been equally effective: just the dates she started and finished recording. “But now it totally looks like I was trying to get publicity or say something to the world. And I totally wasn’t. I do things and they just come off wrong. I wish I didn’t have to take shit for it, because it’s not important enough to me.”

All of which is archetypal Fiona Apple. Make a high-profile, unconventional decision (during your first interviews, discuss how your song “Sullen Girl” is about being raped at age 12; strip to your underwear and cower in a closet for your video), then be surprised when that action, rather than the exceptional music you create, becomes the focus of discussion. Her manager, Slater, denies, though, that these choices are entirely innocent. “I don’t think she’s naive,” he says. “I think she’s very aware.”

Her producer, Jon Brion, feels that “she’s aware of the cause and effect of things, but she’s not calculating in the sense that a lot of people in pop music are. She’s got no problem biting the hand that feeds her if she thinks the hand is up to no good.”

It’s this tension between integrity and commercial expectation, between impulse and calculation, between needing an audience’s love and spurning it, that leads to the divisive sentiments Fiona Apple inspires. And though she claims that When the Pawn…‘s songs of heartbreak, disappointment, and loss weren’t written in response to specific situations, she speaks to real-life matters more eloquently, and less defensively, in her lyrics than she ever will in conversation. On “A Mistake,” she sings “Do I want to do right, of course, but / Do I really want to feel I’m forced to answer you, hell no.” The very last words on the album, in fact, from the lovely “I Know,” are “If it gets too late for me to wait / For you to find you love me and tell me so / It’s okay, don’t need to say it.”

Being Fiona, she says she hadn’t noticed the resonance of these lines, but that she’s not surprised. “I’m a fucking contradicting little kid most of the time, except in my songs. That’s the only time I can actually focus and go, ‘This is the truth about this. This is the way it is.’ And then I write it down so that I can have it in my memory because as soon as I’m done”—she breaks into a laugh—”I’m going to start acting like an idiot again.”

Three days before the album is released, all the conflicting elements of her public perception are very much on Apple’s mind. It’s a chilly L.A. night, and we’re sitting by the pool behind the house she shares with her boyfriend, listening to big-band singer Helen Forrest. After a stressful afternoon, Apple’s indulged in a little tequila: her nerves seem a bit more raw than in the deli the day before. She draws her knees up and hugs them, talking softly into the sleeves of her coat about being the subject of so much scorn, looking every bit as young as she is.

“Sometimes I go, ‘Wow, there’s people that really, really hate me’—and through no personal contact, nothing that I’ve done to them! That means that something about me is hateable to a number of people. I don’t want to just think, ‘Oh, people are stupid, and I hate everyone that hates me.’ But I also don’t want to think that they have reason to hate me.

“That’s not to say that I don’t know why they might be annoyed by me,” she continues. “I kind of see that if all they know of me is, like, some four-second photo someone took. I don’t know what to do with that kind of frustration. Like that kid yesterday—you heard him say, ‘Why do people hate you?’ I’m glad he cares, but that’s a weird thing to hear. I’ve been saying it forever and people are like, ‘Oh, that’s not true.’ And I’m like, ‘Listen. I’m not upset about it anymore. I just think it should be fucking acknowledged.'”

***

“ON THE COUNT OF THREE. I WANT EVERYONE TO CALL ME A fucking asshole!” Fiona Apple orders as she tapes a concert for MTV in a New York City studio. It’s the first time she’s played her new songs in front of an audience, and she sounds impressively strong after two years off the road, confidently navigating the difficult arrangements and tricky melodies. It’s her stage patter that still needs work. On the last tour, shows would often be punctured by painfully long, rambling stories and asides. (“I always know where I’m going,” she says, “but I’m fucking too long-winded. I put too many detours in, never get to the point, and then I forget where I was going.”) Tonight she’s forgotten to introduce the band, which is why she’s having the audience berate her for her “selfishness.” The musicians, studio-slick in suits and hats, laugh nervously—they’re more concerned about getting through the new songs than about getting their props.

“I feel totally in control when I’m singing the songs,” Apple says later. “As soon as I’m not, I don’t know what to say, I don’t know how to act. But I would rather not be contrived, even if it makes me look better. Maybe that’s something that I need to work on. You just kinda figure, ‘Well, I’ll be myself and that’ll be enough.’ But you can be yourself and if somebody snaps a picture at the wrong time, [negative] things happen. There’s so many things that it never occurs to me to worry about.”

But during the making of When the Pawn…, Apple decided that she did need to worry more about her work. She made a concerted effort to take control of the recording process, in contrast to the sessions for her debut. “I have a fucking huge memory of just hating all the songs on the last album when we were finishing it,” she says. “A lot of that record was me going, ‘I don’t know, what do you think is better? Go ahead.’ It just sounds a little bit undecided. I didn’t know enough.”

“On the first record, there was some disparity between the Fiona that you talk to and Fiona the lyricist,” says Brion, who has also worked with the Wallflowers and Rufus Wainwright. “With this record, there are more and more moments that sound like the person I hang out and talk with.”

Apple had another revelation watching Anderson on the Magnolia set. “He is a nitpicker like I’ve never seen before,” she says with a little smile. “But he’d get it right. And sometimes I’m a little half-assed about things. With the last album, I didn’t realize what a joy it is to be able to put things together.”

Anderson—who directed the videos for both “Fast as You Can” and the new single, the pissed-off “Limp”—says the difference was plainly visible. “She’s learned so much, it’s not a learning curve, it’s a straight line. She’s been able to gather information, process it, make sure she’s not being lied to by the people around her, and really make her own record.” He adds that there was a bonus to having another writer in the house. “I was able to pick up notebooks lying around and steal her lines.”

Apple’s goal of assuming responsibility, she says, extends to the places where she has previously gotten into the most trouble. “I really have kinda screwed myself up many times just by letting people do whatever they’re doing—not in a victimizing way, but just because I didn’t realize what the consequences would be. Like, ‘Yeah, sure, take a picture of me like this, whatever’s going to get me out of here.’ But when you feel responsible for something that you’re proud of, it just makes all the difference.”

If there’s a single decision Apple made the first time that she wishes she could change, it’s the Mark Romanek-directed “Criminal” video. While manager Slater says he considered the clip a “tribute to [director Gregg] Arad and [photographer] Nan Goldin,” to most MTV viewers it was just a sex tease—a wide-eyed, scantily clad girl, in the debris of a wood-paneled basement party, looking guilty for who-knew-what illicit exploits. It was as if the video treatment was developed from the song’s first line—”I’ve been a bad, bad girl”—without listening to the predatory aggression and sexual ambivalence of the rest of the lyrics. It would prove to be Apple’s defining moment.

“The shit that got me popular was the stuff that I was not proud of,” she says. “It makes me feel really stupid. I wanted to be like every other girl you see in videos, and that’s why it’s embarrassing. But the way that I justified [the treatment] is that the song is about someone talking to God about a mistake they’ve been making. And so I actually did think for awhile that the video made sense. But I think the thing that screwed it up”—she breaks into laughter—”is how fuckin’ horrified I look. I really look like I’m doing something wrong, instead of playing it with a little bit of a wink. I just couldn’t do it.”

And while Apple’s feelings about the video are undoubtedly sincere, it’s a lot easier to renounce your decisions after you’ve sold three million records. Note, however, the simple., improvised video for “Fast as You Can,” and her refusal to let herself be heavily styled for photo shoots.

The other moment that burned Apple’s loose-cannon image into the public’s brain was the rambling, impassioned speech she gave when accepting the Best New Artist trophy at the 1997 MTV Video Music Awards. “Maya Angelou said that we as human beings at our best can only create opportunities,” she said, words tumbling out of her mouth faster than she could process them, “and I’m going to use this opportunity the way I want to use it… Everybody that’s watching, this world is bullshit and you shouldn’t model your life about what you think we think is cool and what we’re wearing and what we’re saying and everything. Go with yourself.” Pretentious? Self-important? Maybe, but let’s also remember that she was barely 20 years old at the time—and that if Steven Tyler gave the same rap, he’d probably be celebrated for upholding rock’n’roll’s grand fuck-you tradition. In contrast to the “Criminal” video, Apple proudly considers this speech a positive turning point.

“I will never, ever regret what I did,” she says emphatically, her voice rising. “Because I remember sitting in the audience, and making the conscious decision that I didn’t know what I was gonna say, but that I was going to get my feelings out up there.

“I was there thinking, ‘I’m in high school. I’m in a cafeteria. I have to walk by people that are going to laugh at me.’ Instead of just walking by and feeling like I’ve been intimidated like that a million times, I didn’t want that to be who I was. This cool feeling of wanting to take responsibility and make decisions for myself and not feel like I had to hide my emotions—that was a great thing. Now, I don’t have the feeling like I’m the kind of person who never speaks out. Now I don’t have that itch anymore.”

In fact, speaking too much became as much of a calling card as her sultry, prematurely knowing voice. But when she repeatedly brings up how proud she is of When the Pawn…, how happy she is to be working with friends on her videos, how she’s coming to terms with her feelings about being in the spotlight, it’s clear that as painful as many of her experiences have been, the journey has been worth it. Second albums are where rock stars often slip and fall—after putting their whole lives into their first record, suddenly they have to meet artistic and commercial expectations, to write through the grind of touring, to deliver something on a schedule. For Apple, the experience has been almost exactly the opposite of the so-called sophomore slump.

“I feel really secure and excited that my need for recognition isn’t so big anymore,” she says. “It’s like, if you’ve just broken up with someone, and you’re not over them, and you run into them in a coffee shop, you worry about your appearance or whatever. But once you’re over them, you don’t care. And there’s no reason for you not to care anymore—they’re still the ex-one, they still hurt your feelings. But because you don’t have that neediness and because you don’t have that insecurity about yourself, you don’t care that same way.”

***

IN EARLY 1998, JUST BEFORE SHE WENT INTO THE STUDIO TO START work on what would become When the Pawn…, Fiona Apple told me, “Nothing’s changed with me—I still have problems with people, I still need to write the songs. If I didn’t need to, they just wouldn’t be that good. It wouldn’t be worth doing.” Listening to her talk now, two years later, you have to wonder: Will her newfound confidence break her of her need to write? Will little Fiona, happy at last, no longer be able to draw on exactly those emotions that have helped make her the greatest songwriting hope of her generation?

She, for one, isn’t concerned—not about that issue, anyway. “If I had that kind of confidence and I didn’t hurt as much as I do, then I probably wouldn’t write, and it wouldn’t really even be a bad thing. But I’m always going to be a really sensitive person. I’m always going to feel and hurt a lot and be really worried about everything.” She pauses, and aside from the soft big-band swing coming out of her boom box, the L.A. night is still.

“Maybe I won’t be so ashamed now of being that way. Before I said, ‘I want to make it cool to be sad.’ And now that sounds really weird to me. I don’t want it to be cool to be sad anymore. I just want it to be okay.”