Since we last heard from Liz Phair, circa her third album, the awkwardly titled "whitechocolatespaceegg" (1998), Chicago's alternative-rock ingenue has weathered the end of her marriage to filmmaker Jim Staskausas, moved to Los Angeles and largely devoted herself to raising her 6-year-old son, Nicholas.

Many in the Wicker Park music scene that spawned her assumed that Phair had abandoned her musical career, which started as a lark when the onetime Winnetka resident and visual artist began making four-track recordings of smart and sassy songs about the plight of being a smart and sassy woman in a male-dominated rock world.

Those tunes first won attention on the D.I.Y. "Girlysound" cassette, which led to a deal with Matador Records and a brilliant and audacious debut, "Exile in Guyville" (1993), a double album that Phair portrayed as a song-by-song "post-feminist response" to the Rolling Stones' decadent classic, "Exile on Main St." (1972).

The disc was hailed as the album of the year in the Village Voice's annual poll of American rock critics, and it paved the way for a wave of imitators, from Alanis Morissette to Tracy Bonham to Fiona Apple. But Phair, now 36, has yet to match that accomplishment, either in the studio (where subsequent efforts have suffered from a lack of focus) or onstage (where she remains a reluctant and hesitant performer).

Now, with the self-titled "Liz Phair" (Capitol), the singer-songwriter is devoting herself to scoring the mainstream hit that has so far eluded her. She yearns for a feel-good ditty as ubiquitous and innocuous as "Soak Up the Sun" by her friend Sheryl Crow, which found Phair adding backing vocals, and she proves that she's willing to pander to sexism (she appears naked on the cover but for a guitar) and the demands of the pop mainstream (parts of the disc were produced by The Matrix, the platinum-selling production team behind Avril Lavigne's "Let Go") in order to get it.

Phair is no Crow (she lacks the sophistication) and she's certainly no Lavigne (she's never been that naive, energetic or blissfully bubblegum). The result is one of the most tragically compromised records that a once-uncompromising artist has ever made.

When The Matrix isn't polishing the disc to an overproduced sheen that makes the music so slippery that it's nearly unlistenable, L.A. rock stalwarts Michael Penn and R. Walt Vincent (producer of Pete Yorn, who makes a guest appearance playing all of the instruments on the disc's most controversial track) are simply boring us with that California folk-rock sound that was a cliche when Linda Ronstadt was still at her peak.

Phair is still capable of crafting memorable melodies (witness "Little Digger", a tune that finds her showing a rare flash of that old blunt honesty as she tries to explain to her son why Mommy is dating a new man). And her singing has greatly improved since "Exile" (somewhere along the way, she accepted the frequent criticisms of her limited, monotonous vocals and took singing lessons).

But on songs such as "Rock Me", "Bionic Eyes" and the single "Extraordinary", you can hear the artist crassly calculating her moves, listening to how the lyrics and the arrangements will sound on the radio (which has never supported her, anyway) rather than giving it to us straight from the heart.

The nadir is the Yorn-driven track "H.W.C.", a reference to a bodily fluid that can't be named in a family newspaper. This risque celebration of fetishistic behavior attempts to out-scandalize Madonna, but it winds up sounding like a desperate bid for attention from the leering Howard Sterns and Mancow Mullers of the world.

In interviews, Phair claims that she was reinvigorated by the challenge of attempting to broach the pop mainstream, and that she made exactly the record she wanted to make. But the fact is that longtime fans won't find much to embrace in this *1/2 effort.

Several weeks after Phair did a public interview before several hundred fans at the South by Southwest Music & Media Conference in Austin, Texas, last March, I had my own, more intimate conversation with the artist. Here are some of the highlights:

Q. I saw the interview you did at SXSW with Neil Portnow, the head of the National Academy of Recording Arts & Sciences, and the questions were just terrible. You had to do all of the work.

A. Yeah, it was like someone just went through the press clips and was paraphrasing--like back in junior year of high school, when you didn't want to really do the work.

Q. So what's the toughest question you would have asked yourself if you were conducting that interview?

A. What's the toughest question I would have asked myself? "What are you planning to do about alienation of past fans?"

Q. That's a good one, because some people are going to damn you for working with The Matrix, or because you moved to L.A.

A. The L.A. thing--don't you think that's a little much? That's the psycho fringe.

Right before I left, I was in I forget what bar--like the Zebra Lounge or something over on Western--and some woman nearly punched me for leaving Chicago! She was drunk, but she wanted to really pick a physical fight. And I just thought, "Oh my f---ing god! You're crazy!"

Q. Billy Corgan doesn't get that kind of crap.

A. Yeah, but he was so troubled. He was kind of all f---ed-up or whatever. [Laughs]

Q. Does your former producer Brad Wood, who also moved to L.A., get that, too?

A. Well, Brad is kind of like Grandpa, so he has a lot to complain about at different times. But he said he was so tired of being in Chicago because he felt hated in Chicago while he was there. He felt like he was constantly being approached while he was out at night to justify himself. He was like, "I'm just sitting here drinking, I don't want to take on some sort of philosophical thing with someone about why I work the way I work." I think Chicago has that, though, and I have a theory about it. Want to hear my theory?

Q. What is your theory?

A. My theory is there is not enough money being put into middle- to high-level creative endeavors other than advertising. There's a tiny little pie to go around, and if you're like young and just starting out, it's kind of a Mecca. You're not really using that much money, so it's kind of what makes it culturally interesting and an embraced part of Chicago, even by the mainstream. But once you get to a certain point and want to build, like in New York or L.A. ...

Everything about L.A. here, you can have like the Rick Rubins of the world with massive houses, you can meet people who are artists and weird who have a lot of money, and there's all these different opportunities. You can bring a film thing in, or there's just so many people who can make money here that it's not so tight-fisted in terms of, "Will I help you get to the top" or "Will you help me?" or "If you get to the top, are you taking all the rest of our spaces?" It's like an NBA team: If one person's getting paid a lot, no one else gets any money.

Q. But it also keeps you honest. In New York and L.A., you're constantly surrounded by people in the industry. Here in Chicago, you can't possibly avoid your fans, and they don't hesitate to tell you what they think of your work. In L.A., if you play a small club like the Viper Room, everybody who's there is "somebody."

A. But that's because you're in L.A.!

Q. But isn't that artificial?

A. But it's a home base. It's like playing inside the house. I mean, the same band that is having this artificial environment in the Viper Room makes an hour drive to Santa Barbara, and it's straight fans.

Every time I go to the grocery store, I meet [real fans]. You don't just play in L.A. Pretty much you're playing 95 percent of the time in markets where you are in contact with the fans for real. And there's a lot of people in L.A. who are fans themselves who may or may not work in the industry.

It's like, no one's being protected here because we don't do our work here. We do the business work here, but when we do the real stuff we're out on the road, anyway. It just allows you a place where you feel like you have more peers.

I felt like a freak, Jim, in Chicago because I could either be a housewife or this slut. There was no integration. I felt really split, and I always felt guilty if I dressed weird or sexy because, you know, "Ooh, she's that dirty slut who sang those dirty lyrics." Or if I went to Wicker Park and I looked cute and like "Mommy," it was like, "Oh, my god, she's so lame." There was no integration of artist and normal person, whereas here everyone gets it.

I always thought the only thing wrong with Chicago is that it didn't promote itself. It kind of kept that "keepin' it real" mentality, but if Chicago took the wild artists that it certainly has and put them on a platform and said, "These are our valued citizenry, come to Chicago and check out the arts festivals," there would be more people bringing money in, there'd be more tourism, there'd be more just appreciation around town. It wouldn't be so sanctified.

Q. This brings you back to your own toughest question: The people who say you're alienating your old fans are going to say you're no longer keeping it real.

A. We'll see. When I listen to the record, I feel like I'm hearing myself. It's a part of myself, and there are a lot of songs that are a really big part of where I am as an artist that didn't make the record.

Some I want to put on the Web site, and those are a different kind of more challenging songwriting. So that in my mind is still a whole big part of this "campaign," so to speak, that's part of who I am now and it's going to come out.

The record is designed to work for a major label. It's consciously designed to be something that can go through that avenue and hopefully do it well, while at the same time kind of bringing self-esteem stuff to women and just letting me be kind of brash and outspoken the way I like to be. You know what I mean? It's a good question, though.

Q. Why does broaching the mainstream and succeeding in the major-label world matter to you? When I first talked to you 10 years ago, you never talked about how many copies "Exile in Guyville" would sell. It wasn't even on the agenda.

A. Now music has become something that I've invested my competitiveness in. It doesn't mean--and this is the God's honest truth--when I write a song, I'm never thinking about how people are gonna receive it, because I can't write songs that way. They just come out. They're still very true and pure that way.

The ones that I tried to write a certain way, they're not on the record, and they're not something that I'm going to release, because they're bad. I feel it. But I think music, because of the attention and the interest that happened with the first record, there was no way to be innocent again. There was no way not to feel that you were in an arena that was different from the one you'd been in before.

Q. You've said that you had 40 or 50 songs to choose from for this record. What's the wildest song that you left on the cutting-room floor?

A. The wildest songs are actually on the record--the kind of biggest, brashest, coolest moments. I think of this record as being a lot about music. What I like about it are the musical moments; it's very much about music to me.

It's like we should have called it what my son told me to call it: He wanted to call it "Rock Band". That's sort of what it's about to me. It's like I'm pretending to be in a rock band. A lot of what I love about it, why I chose the songs I chose, is because of the music--the guitar moments and the energy in the drums and whatever coming together at different points.

The stuff that didn't make the album tends to be slower, more depressing, and not necessarily conflicted, to be honest. Some of the stuff that's on here is the conflicted material. And a lot of the stuff that didn't make it is the kind of songs you write that are kind of slow and kind of sad.

Q. So do you think you're going to have a multiplatinum pop hit?

A. Who knows? [Laughs] But the only thing that's OK about it, Jim, is like, I don't know if it's gonna sell records. We're gonna try. But I put the songs on the record that I wanted because I just wanted them there, because this one, I just felt like making a really rocking record. I wanted that kind of strong persona, and if it doesn't work, it doesn't work, but I'll never look at the album I made this time especially and go, "God, I shouldn't have tried to do that."

I'll have no regrets, and that's one of the things that I always want to make sure. Sometimes when you listen to other people and you do what they think you should do, you end up learning from their mistakes, and it's not the same as learning from your own mistakes.