Smart was supposed to make her a superstar. Something better happened.

"Weave my disgust into fame," Liz Phair sang, " and watch how fast they run to the flame ." Then it came true. At the beginning of 1993, nobody except a few Chicago scenesters knew who Liz Phair was. At the beginning of 1994, her instant-classic debut album Exile in Guyville had topped the Village Voice's annual Pazz & Jop critics poll and sold more copies for its label than the company had ever sold before.

Everyone wanted to know: What was next? Major-label executives crashed the Wicker Park recording studio where Phair, alongside her co-producer and bandmates, was trying to record new songs. The Chicago music scene gossiped, whispered, and argued about Phair's success. Phair talked to reporter after reporter; it was not unusual for a 1994 profile of Phair to include a moment in which she had to interrupt her conversation with the writer to conduct another interview with someone else. "Her phone," the Chicago critic Bill Wyman wrote, rang " literally incessantly ."

Those interviews are a roller coaster to read now. Phair was so obviously panicking; half the time, she's making bold proclamations about her own ambition, and half the time she's questioning whether she wants to make music at all. She was being promised stardom and riches, but she was mostly experiencing the downsides of fame, and very little actual money had arrived in her bank account. (One much-needed check, from her publishing company, was eaten by her boyfriend's pet rat. " That was an interesting call to make to my accountant ," she later said.)

Amid the chaos, she recorded a batch of new songs in Chicago and, when Chicago got too crazy, during a blissful nine days at a studio in the Bahamas. The result was Whip-Smart, an album released by Atlantic in an unprecedented six-figure joint venture between the major and Phair's indie label, Matador. In this transforming pop environment—when "alternative" artists like Beck, 4 Non Blondes, and 10,000 Maniacs could crack the charts—Atlantic had Top 40 dreams for Phair. Its president told Billboard he was confident the record would go gold in no time. Things didn't quite work out that way.

Last summer, the 30th anniversary of Guyville was attended by retrospectives , special reissues , and a celebratory tour . This month, Whip-Smart's anniversary came and went without fanfare. But it's a remarkable album full of expertly crafted songs, and I'd argue that its story is as important, when considering the alternative rock explosion of the 1990s, as that of its more-lauded predecessor. I spoke to Phair, her bandmates, and label execs about how Whip-Smart was recorded, why it didn't make her a star, and why it sounds so good now, three decades after its release.

It's hard to imagine a more destabilizing path to indie-rock notoriety than the one Liz Phair took. Instead of playing small clubs, growing an audience, and working her way to recording success, Phair sat in her childhood bedroom in suburban Winnetka, Illinois, making cassette tapes of herself singing her dark, funny pop songs. She gave the tapes to a few friends, who circulated them through the Chicago scene—eventually landing Phair a record deal with Matador. When it was released in 1993, Exile in Guyville, an ambitious collection of fully produced songs off those original " Girly-Sound " tapes, instantly made Phair an indie heroine, feminist icon, and sex symbol, at the age of 26—but she still had basically zero experience playing live.

"I'm not a performer," Phair told me on a phone call from California, where she now lives. "And all of a sudden, I was in front of an audience." Her first shows were nightmares. Phair fumbled through songs, broke strings, strained her voice, often seemed lost. " I wouldn't come to my own shows ," she said at the time. Reviews were rough, frequently singling out her guitar playing for criticism, but often counseled patience. "Likable but not yet riveting," the Chicago alt-weekly called her , allowing that it's difficult to be "growing up in public."

Meanwhile, the phone rang off the hook. Each morning, Phair had to call a Matador publicist and find out which reporters she was scheduled with that day. Even sympathetic interviewers echoed the sniping going on behind her back in Chicago—" I heard you sucked Gerard [Cosloy] off to get the Matador contract ," the zine publisher Lisa Carver confided, referring to the label's co-owner. ("Of course not!" Phair replied. "Don't be stupid.") The producer and rabble-rouser Steve Albini wrote an infamous letter to the Chicago Reader in which he, among other things, called Phair a modern-day Rickie Lee Jones: "more talked about than heard, a persona completely unrooted in substance, and a fucking chore to listen to."

Sometime in 1994, she appeared on MTV's alternative-rock showcase 120 Minutes , and her interview there encapsulates everything she was going through. At times she's forthright and hyperambitious, making a case for Guyville's conceit—a profane, track-by-track response to the Rolling Stones' Exile on Main St. But when the host asks her if she's gotten more comfortable playing her songs live, she nervously starts rocking side to side. "I vacillate between thinking that it's a really good idea for me to pursue this," she says, "and then sometimes I think, What am I doing here? Why am I doing this?"

"I was so confident on Guyville!" Phair marveled to me. "I knew exactly what I was doing." But the outsize success of the album in the small world of indie rock threw her. "We had no idea why that had happened. It messes up your head." In trying to follow it up, she told me, she was dealing with the ramifications of that newfound visibility. "The boulder in the pond of Guyville, which had sent all those ripples out, had not settled."

Brad Wood, who co-produced Guyville with Phair in Idful, his Wicker Park recording studio, recalled that it wasn't exactly as if everyone came in intending to make a follow-up. "We just never really stopped recording," he said from Los Angeles, where he now runs Seagrass Studio. "Liz still had songs she wanted to continue to work on, so we would book time in the studio when she had something she wanted to try." Wood's work on Guyville had made him an in-demand producer, overseeing records from Sunny Day Real Estate, Ben Lee, and Veruca Salt, which financed upgrades to all his equipment: "new tape machines, a brand-new recording console built just for our purposes, all-new wiring, cabling, everything." Listening to Whip-Smart, he said, he can hear himself learning to use his new equipment from song to song.

Over weeks stolen here and there, the three musicians who'd built a rapport during Guyville—Phair, Wood, and guitarist Casey Rice—laid down backing tracks. "When Liz brought in a song," Wood recalled, he'd first record her playing guitar to a rhythm track, "usually just a percussion part that I'd played or Casey had played." Once her guitar and temporary vocals were recorded, the three of them would work out what else the song needed: Wood played drums and other instruments, while Rice contributed lead guitar. Finally, Phair would rerecord the vocals until the performance suited her.

The album's egalitarian final credits eschew the word producer: They note that the record was "recorded and mixed by Brad Wood and Casey Rice" and list Phair as the "director." That seems like an accurate description for Phair's authority in the studio. "It was always Liz making big decisions," Wood said. "Doesn't mean I didn't have leeway. I had a good working vocabulary of what musical ideas Liz would respond to. But Liz always had veto power." Rice, in a call from Australia, agreed: "We got to try out different ideas and sounds, but it wasn't a consultation process. She was very autonomous in her decisionmaking."

Phair told me that her first songs for those Chicago sessions were all about grappling with her sudden prominence. "But then my attorney was like, 'Liz, no one wants to hear 12 songs about you struggling with being famous.' I was like, 'Fuck, fuck, fuck.' " She repaired to a cabin in Michigan to write on her own, crafting songs about her current relationship, with Jim Staskauskas, the film editor who'd worked on her "Never Said" video. She was living happily with him, his 14-year-old son, and the pet rat in a carriage house in Bucktown, and he inspired songs like the lover's ode " Supernova " and the envious snarl " Jealousy " ("I can't believe you had a life before me").

At times, the atmosphere inside Idful could be magically creative. Wood recalled Rice coming up with an innovative idea to capture the "watery, dreamscape guitar sound" they wanted for "Nashville," a beautiful torch song that Wood considers one of the best tracks he's ever recorded. As Phair played her guitar part, Rice stood on a chair in the middle of the studio's enormous live room, slowly swinging a thrift-store lavalier microphone by its cord in wide circles so that the mic passed near speakers at either end of the space.

"If Liz made a mistake, we'd have to stop and start all over again," Wood remembered. "And Casey's arm got more and more tired, even though Casey's a plenty strong person. I think we built a little armature sort of support, for the arm, so Casey could keep swinging this thing overhead. That's what gives the song its hugeness and mystique."

But Phair was feeling the pressure. It wasn't from the label, though everyone at Matador made it clear they were very eager for new music. "It came from self-consciousness," Phair told me. "Everyone looking at you for answers, when you were just an idiot kid five minutes ago." She and her bandmates, she said, felt they had to do something worthy, and they were starting to fight.

Plus there were the phone calls, the visitors, the rigmarole. "I had to do photo shoots, I had to do interviews all the time," Phair said. Rice remembered a revolving door of pals dropping by Idful at all hours, which slowed things down. Then there were the industry people, "coming out of the woodwork," Rice recalled, "which is what happens when you have a phenomenon record that the record companies didn't make. They want a piece of it."

As winter approached, most of Phair's vocals still needed to be recorded, and no one was looking forward to doing it in Chicago. "It was bitter cold, and my studio was not very adequately heated," Wood remembered. Rice thought of Compass Point, the legendary studio in the Bahamas where Back in Black and much of Remain in Light were recorded. "Why not go somewhere warm?" Rice proposed. "I showed her all the cool records that were made there, and she was like, 'What an idea,' and I was like, 'I know, right?' "

And there was money for such an escapade because Phair had finally joined a major label—sort of. Atlantic Records had been courting Matador, eager to distribute Pavement, the label's signature artist. When Guyville came out, Atlantic suddenly found itself competing for her against every other major. Danny Goldberg, then the president of Atlantic, told the press that his first meeting with Phair had been a disaster: "Everything I said was wrong, and she was using swear words." But he told me he made a connection through the person Phair was closest to at Matador: head of publicity Spencer Gates , who talked to Phair every morning. Gates helped persuade Phair to sign on to a joint venture between the labels. This would allow Phair access to hitmaking machinery without selling her independent soul.

Atlantic, Goldberg told me, was desperate to update its rock portfolio, which skewed older and very male. "It was a big deal that we were able to get a highly sought-after, cool artist," he said. For Matador, "it was a way to have their cake and eat it too," said Chris Molanphy, host of Slate's Hit Parade podcast. Matador had watched the Seattle label Sub Pop lose Nirvana to David Geffen's DGC Records after the band's debut, Bleach. The agreement with Atlantic would help it retain a stake in an artist it had discovered.

Phair, Wood, and Rice took that Atlantic money and spent nine February days in the Bahamas, drinking rum, taking long walks on the beach, and recording Phair's vocals. All three of them remembered the session as an escape from everything that was weighing them down on the mainland, and an exceptionally fruitful time. Both Phair and Wood told a story about the two of them going on a late-night walk and returning to the studio to find a bleary-eyed Rice, headphones on, many rum-and-Cokes in, sitting in front of a row of chimes. Rice feverishly shushed them, then—very, very delicately—rang the chimes. You can hear that sound at the beginning of " Nashville ." ("Obviously, I remember that moment less clearly," Rice said, laughing.)

"In Chicago, we were each trying to pull the project toward what we thought it should be," Phair said. "When we got to the Bahamas, it became three kids making a record." By spring, the album was done.

As part of the deal with Atlantic, Phair said, she was told she could direct her music videos and combine them into a sort of short-form film project. She spent part of the summer making the video for "Supernova," the album's strutting first single, a goofy pastiche of effects, attitude, and hot guys rowing boats.

"I kept trying to assert my artisticness," Phair said when I asked her whatever happened to that film project. "I could be a director, sure. Anything to stop what was happening, which was that my job was going to be a performer." The film project never really came together. "I was realizing that a lot of my plans weren't gonna be what actually happened," she said. "It was quite enough to be getting on with just being Liz Phair."

For its part, Atlantic was bullish. Goldberg loved her, even if he didn't seem to really understand her . "There's a quality she has, a weird kind of anticharisma," he riffed. "She wears very little makeup, if any at all, and is very down-to-earth, yet has this odd magnetic quality." He pronounced that the album would "hit gold quickly," and Tod Elmore, the label's national director of alternative promotion—I can't imagine a job title that could sound more 1994—said that "given the current climate at Top 40, we'd be silly not to" milk the album for possible hits. A national tour was booked, with Phair backed up by her studiomates Wood and Rice, along with bassist LeRoy Bach. Rice and Wood remember that shows were already selling out before the album's release.

In the same Billboard story in which Goldberg made his sales prediction, Phair herself tried to tamp down expectations for Whip-Smart, the follow-up to an accidental masterpiece. It's a line my Gen X soul admires almost beyond expression: "I made sure it wasn't shitty," she said, "but didn't worry about whether it was like, A+."

"That's a little bit of me being a brat," she said when I read that back to her, 30 years later. "I can see, as an adult, how frustrating that must've been for all the adults in the room. Like, 'OK, thanks! Helpful!' " She laughed. "Hats off to her."

Later she would describe how she felt that summer, as the fanfare got louder:

All these people wanted me to be really big and I felt like this tiny pea in the center of all this chaos. I didn't want this success. I kept thinking this is wrong. Why do all these people want it so much more than I do.

Rolling Stone put Phair on the cover , with the triumphalist line "A Rock & Roll Star Is Born." (Spin, then the "alternative" to RS's mainstream, had also wanted Phair for its cover but got shut out at the last minute, reportedly, when RS demanded exclusivity.) The Chicago Tribune delivered a wide-ranging, 5,000-word cover story in its Sunday magazine, retelling the Phair legend for a broad hometown readership. Writer Greg Kot quoted Albini ("a rich suburban girl who made a name for herself (by) having an incredibly aggressive publicity campaign") and the head of indie label Thrill Jockey, who tartly noted that plenty of other great female songwriters didn't pose topless on their album covers.

But Kot also gave Phair plenty of space to talk, and she talked. Overcome by doubts about the path she was on, dreading the coming tour, yet doing her best to play the role, Phair delivers quote after quote, almost reflexively contradicting herself. She oozes determination: "Damn straight I'm manipulating my career and the media." If she weren't becoming a rock star, she claims, she'd be "blasting into offices somewhere else wanting to get to the top of the corporation. It's ambition. Total, simple ambition."

But she's also already looking past her time as a performer, wondering what a different life might be like. She muses about skipping straight to the end, getting married and having babies and avoiding touring entirely. "Is that any way to sell a half million records?" she asks, laughing. Then she says, in language that might have sent a chill down Danny Goldberg's spine: "I have this real dark feeling that this year I'm going to do what I'm not supposed to."

Whip-Smart begins with the sound of Phair playing "Chopsticks," the first song every student learns on the piano—a wink, perhaps, to her now-notorious lack of chops. She tells a story of picking up a guy, delivering her tale in a seen-it-all deadpan: "He said he liked to do it backwards. I said that's just fine with me. That way we can fuck and watch TV."

For listeners who'd spent more than a year wearing out Guyville, with its one-night stands and horny come-ons, "Chopsticks" felt like a kind of corrective, a reminder that there was more to the singer than the characters she played in her songs—an argument she'd been making all along. " I didn't lose my virginity when I was 12, and I don't want to fuck everyone until they're blue ," she told a reporter. "People expect me to be Liz Phair all the time, but I'm Elizabeth Clark Phair and I have an entirely independent existence." Yet by then, her performances were often interrupted by bros in the crowd shouting, "Nice ass!" In a metaphor that stopped me short when I read it, she compared Liz Phair with a hand puppet—one she often wears herself, but that "everybody gets to stick their hand up there and go at it for a while" too.

At the end of "Chopsticks," as guitars howl in the deep background, the singer drops the guy off and drives home. "Secretly, I'm timid," she says.

After that song and its follow-up, "Supernova," Phair avoids the kinds of straightforward messages that dominated Guyville. The songs are knottier, the metaphors intentionally muddled. Who is the "X-Ray Man"? What does it mean when Phair snarls, in "Support System," "Wrap me in steak, why don't you? Throw me in the panther cage and maybe then I'll like you better"? What does it then mean when the backup singers respond to this by shouting "No way!"

"Guyville was stuck and pounding on a door," she told the New York Times. " With this one, suddenly I had a vista ." That vista may have been clear to her, but the intrigue of Whip-Smart often comes in the way she cracks the door a tiny bit for the listener, allowing us to see only the edges. It's an album of inside jokes, veiled references, and beautiful sounds; an album with a singer who'd rather be sly than impassioned; an album that never blows its cool. That is to say, it's hardly a pop album at all.

On Sept. 29, 1994, David Letterman held up a copy of Whip-Smart while introducing the Late Night audience to "one of the most interesting new artists of her generation." Performing "Supernova," Phair initially seems a bit overwhelmed but by the end of the first verse looks confident and composed, tossing off the song's raunchy endearments with aplomb. Brad Wood grins as he pounds the drums. Casey Rice lets the song's short guitar solo echo a little longer than usual, shredding into the final chorus. When it's done, Dave comes over, shakes Phair's hand, and, as the show goes to commercial, delivers a Lettermanian non sequitur: "You need a lawyer?"

It was the apogee of the Whip-Smart publicity wave. It was also the last time Phair, Wood, and Rice would perform together. "That was really exciting," Wood told me. "But it was also really bittersweet for me, and I imagine it was for Casey too, because we had just found out that this was going to be it. So I still watch that and feel sad."

Whether Letterman knew it or not, Phair's lawyer was indeed busy around Whip-Smart's release, because Phair had informed Atlantic she was canceling her tour. The label did not take it well. "I got really intensely worded letters that were like, 'You got a big advance, we expect you to tour, we're not kidding, here's our attorney,' " she told me.

"She jumped off the train when the trajectory was going upwards," Rice said, "and that was a bummer."

Thirty years later, Tod Elmore, the onetime national director of alternative promotion, doesn't remember a lot of details of the Whip-Smart release, but he does know that canceling a tour would make selling the album a lot more difficult. "Touring was a massive marketing device," he told me from Atlanta, where he now runs a live-music production company—especially, he said, in the days when most media was still local. Getting an artist into markets across the country was how you got her into local radio stations, local retailers, and local newspapers.

Wood still bemoans the missed opportunity. "I really, really wish we would've done that tour," he said. "I think everybody in the band, besides Liz, was very excited to do it, but it was her decision. But that's her story to tell."

"Picture something you're really, really scared of doing," Phair told me. "Something you always avoid. Now picture that's your job." She elaborated in a written interview with a fan site in 2009:

When I canceled the tour I was a basket case. I was thinking that I was way in over my head and I was the biggest hypocrite of all. I hated what I was doing. I could've got a job like I was supposed to after school in a respectable profession. I would have hated my job, but so what. Instead I was writing music that I loved and it turned into a job that I hated.

Most everyone I spoke to described the decision to cancel the tour as the smoking gun in the case of Why Whip-Smart Didn't Make Liz Phair Famous. But I'm not convinced it's that simple. "Alternative" as a category suggests a kind of big tent for all sorts of music, but in 1994, alternative music was still living in the shadow of Nirvana. "Supernova" peaked at No. 6 on Billboard's Modern Rock chart in November (it hit only No. 78 on the Hot 100); that week, the Top 20 included Nirvana, plus Stone Temple Pilots, Live, Smashing Pumpkins, Hole, Dinosaur Jr., Soul Asylum, and two songs by Soundgarden. Not all those bands were grunge, precisely, but that's a lot of dirgey, distorted guitar.

"I often look at '94 as the apex of grunge in the alternative sweepstakes," said Molanphy. It's true that songs that didn't fit the most reductive grunge stereotype could succeed in 1994; that very week, the No. 1 song on the Modern Rock chart was the Cranberries' own spin on the genre, with "Zombie." But other than Beck's "Loser," an out-of-left-field smash earlier in the year, the songs that topped the Modern Rock chart featured powerful guitar, powerful pipes, or both.

"Asking Liz Phair to do that is a tall order," pointed out Molanphy. Even on "Supernova," with its crunchy guitars, Phair's vocals are crafty, understated. "Whip-Smart is a really good record, but she's not really trying to grab the brass ring." He compared her with another Matador band who also had its biggest chart hit in 1994, thanks no doubt in part to Atlantic promotion: Pavement. "Is 'Cut Your Hair' catchy for Pavement? Yeah. Is it still very weird compared to Candlebox? Absolutely. There's a ceiling on something like that."

For his part, Goldberg now agrees. "She probably would have sold more records if she'd toured, but I don't think it was a gigantic act of self-sabotage," he told me. In his estimation, Phair was carving out new territory for Atlantic and for herself. "Rock was a male art form, by and large, and in '93, '94, you had women finally finding major platforms—Courtney Love, of course. PJ Harvey. Liz spoke from another point of view, a more educated, middle-class point of view, rather than coming up from punk. It was a psychological and cultural territory that she really invented, a new space she created just by the brilliance of her lyrics."

Only a few months after Whip-Smart's second single, the title track, dropped off the Modern Rock list—it peaked at No. 24—a new singer topped the charts with a fascinating pop spin on the Liz Phair formula. At the time, I remember thinking—a little bitterly—of Alanis Morissette's "You Oughta Know" as training-wheels Phair: a song that gave the lyrical forthrightness of Guyville a glossy pop sheen, sung by a woman who could absolutely belt. It's not clear that Phair could ever have delivered such a song. Even nine years later, when she took a hard pop turn with Liz Phair, she still didn't have the pipes to take "Why Can't I?," her lead single co-written and produced by the Matrix, higher than No. 32 on the Hot 100. But in 1994, at least, she didn't want to deliver that song. She was still struggling with what fame might mean, what living as a performer might doom her to.

Though Phair took her lawyer's advice not to make all the songs about her uncertainty with fame, that caution still animates much of the album. Reviews at the time—all of which were strong, even if no one thought the record was as good as Guyville—often mentioned that several songs on the album repeat the same line over and over. (The motif is almost little-girlish; at one point, Phair considered calling the album Jump Rope Songs.) "Shane" fades out with Phair intoning, "You gotta have fear in your heart." "Nashville" ends, "I won't decorate my love." In a four-star Rolling Stone review , Barbara O'Dair mused, "Taken together, [those two lines] might even serve as a thumbnail of Phair's rules for living." I don't know if that's true, exactly, but those lines—and the songs they appear in, both of them beautiful and elusive—certainly reflect Phair's feelings about success in 1994.

But how does the album sound in 2024? I don't know that I can make an argument that the current pop landscape is one in which Whip-Smart might flourish. Certainly, female singers are not shy these days about their sex lives. Maybe someone somewhere is even making a case for Sabrina Carpenter's aloof delivery as a kind of nü-Phairian deadpan. But come on. Whip-Smart doesn't sound of our time any more than it sounded of its own time. That was what I loved about it then, and that is what I love about it now: It is the sui generis product of a trio of talented, creative artists working together to make a brilliant songwriter's challenging songs sound great, in a way that's all their own.

And they really sound so great! The almost comically loud bass on "Go West." The uncommonly jaunty, whistled choruses on "Support System." Phair's growled warning in "Crater Lake" that "dynamite stuffed in a mailbox doesn't smoke until it blows." And "May Queen," one of Phair's best songs, on which the three musicians shamble as one to anthemic heights, and Phair dismisses out of hand the kind of man who, maybe even earlier in the album, might have intrigued her: "You were miles above me/ Girls in your arms/ You could've planted a farm/ All of them hayseeds."

Whip-Smart is not a landmark, like Guyville. It's not a flashpoint, like 2003's Liz Phair. It's simply a terrific album, one that rewards revisiting in a way that most albums from 1994 do not.

It's not even a failure, really. By almost any standard, it did great. It sold more than 600,000 copies and did, indeed, go gold, though it took five years to do so. It was a failure only by the measure that Atlantic had set for it, a measure that Phair struggled with, embraced, then rejected. In the gulf between its actual performance and how it was viewed—by the label, by Phair, and by fans—rests the entire story of the 1990s alt-rock revolution, when so many innovative artists found themselves considered disappointments for succeeding at levels they'd never dreamed possible.

"It doesn't feel tainted or polluted by the stuff that was going on around us," Phair said when I asked her how she felt about Whip-Smart today. "For the most part, that record is a wonderful snapshot of us succeeding at staying true to ourselves in the middle of the chaos."

Phair is "probably the best lyricist of my generation," Wood said. "Had she just put out Whip-Smart as her debut album—it's a pretty great record."

"I met myself back in that record," Phair said, "at a moment where I'd lost myself."