We’ve Got A File On You features interviews in which artists share the stories behind the extracurricular activities that dot their careers: acting gigs, guest appearances, random internet ephemera, etc.

For many, the last new music they heard of Liz Phair’s was 2010’s Funstyle, a critically maligned digital download where the singer/songwriter could be heard white-girl rapping on a song called “Bollywood.” Looking back at that time, Phair says flat-out that Funstyle was absolutely not a studio album, and definitely nothing to be taken seriously. “I just thought it would be fun to put out like, a clean-your closet [record], hear the outtake-y thing,” she says over the phone. “That’s why I call it Funstyle. But it was like, this is not a proper Liz Phair record.”

According to Phair, the last real studio album she put out was 1998’s Whitechocolatespaceegg, which represents something of a career crossroads. Her third LP arrived five years after the explosive success of her debut, 1993’s Exile In Guyville, which made her an instant indie-rock icon, and five years before her 2003 eponymous album, a popified, radio-ready venture that famously put her on a lot of purists’ shit lists.

Even though the narrative has shifted around Phair’s major-label effort, thanks to a little hindsight and some poptimism, she wouldn’t call her early aughts effort a proper studio album either. Instead, she refers to Liz Phair as a combination of live band recordings, plus three or four songs she made with super-producer Michael Penn. It’s her forthcoming album, Soberish, that’s the real studio venture — her first since Whitechocolatespaceegg.

For Soberish (out June 4), it makes sense that Phair would reconnect with producer Brad Wood, who helmed Guyville, its 1994 follow-up Whip-Smart, and the aforementioned Whitechocolatespaceegg, all of which were released on indie incubator Matador Records.

For Soberish, Phair intentionally mined her lo-fi Guyville aesthetic for inspiration, then built on it with a contemporary perspective. “I wanted to use the same building blocks, but then put ourselves in an uncertain place,” she says. “Not make the songs expected, not make them known entities, but find our way into each song so that it revealed itself anew to us and surprised us. A lot of that meant we recorded songs a few different ways. If it didn’t feel fresh and new, built out of the solid past, it didn’t get to come on this record.”

In addition to talking Soberish, Phair revisited three decades’ worth of what she gamely calls “weirdo moments.” These include, but are not limited to, a 2001 Apple commercial where she once stood on a stage with George Clinton and Barry White, playing herself on Charmed, “Why Can’t I?” getting the needle-drop treatment in 13 Going On 30, and much more.

“Blood Keeper” (1997)

You had a Whitechocolatespaceegg outtake called “Blood Keeper” that was intended, at one point, to appear on the Scream 2 soundtrack. What do you recall about that time in your career? I assume you’ve heard the Speedy Ortiz cover?

LIZ PHAIR: Did I hear that Speedy Ortiz did a cover of it? They toured with me and Sadie [Dupuis] would come out. She was going to play it and then I said “No, you can’t. I want to play it, and then you come and sing it with me.” So we did it on a regular basis in 2018 on our tour together. Over and over, it would bust my voice. I write songs that I don’t necessarily think I’m going to perform live often and they’re not necessarily my range. I have a real blind spot for writing outside of my own vocal range, and every time I’d sing that song, it would shoot my vocal cords for the rest of the set and I’d say, “Damn it.”

It was so fun to have Sadie there. She’s got an angelic voice and she’s so game, up for anything. The fact that a peer of mine resurrected that song singlehandedly [and] had appreciation for it… She and I just naturally get each other. It was such a weird song born of the pain of feeling like this job of… I make art. I can make visual art. I can make sonic art. I can make dramatic art. You name it, I can make art, but performing, being on stage, is something that sometimes I feel I totally own it; sometimes I feel why am I up here, what am I supposed to be doing? I’m a total fraud.

So, “Blood Keeper” was born of this angsty self-reflection of “nobody gives a fuck as long as I’m up here.” I feel I do it right, save time, make love, feel fine about everything. It was that busy period of adulthood when your functionality becomes more important than your personhood and then standing on stage coughing up another piece of myself for an audience. I kept imagining that my nose… What do you call it when you get a bloody nose? It just ran down. I felt that’s what I’ve seen that something humiliating was happening to me onstage, but the audience just wanted more. Give us more of yourself.

It was about that, fulfilling my functions. It reminded me of “Canary” actually, a song on Exile In Guyville, when I’m talking about performing my duties, like cleaning the house, arranging the books, practicing my piano. And inside, seething with that disaffectation… Is that the right word? That might not be the right word.

I see where you’re going.

PHAIR: Just feeling that it’s a little bit horrific in a psychological way.

I honestly can’t believe I forgot that you had performed that song on tour with Sadie.

PHAIR: She’s sometimes better than [when] I do it. I don’t know why, I was selfish. I’m like, “You come on my set.” I think I was looking for extra special things for my set because I was feeling insecure.

Backing Vocals On Sheryl Crow’s “Soak Up The Sun” (2003)

Speaking of things I never realized until I researched this File, are many of your fans aware that you did the backing vocals on Sheryl Crow’s “Soak Up The Sun” in 2003?

PHAIR: No. Hardly anyone even knows and understandably so. There’s not much to my part. I’m just doing the alto harmony on the choruses. I can hear myself and I think when you know it, you can hear yourself and hear me singing. There’s a YouTube video online where Jay Leno has us [performing]. It really explains how it came about.

How did you originally connect with Sheryl?

PHAIR: We knew each other from Lilith Fair. I was a little bit of a rascal on Lilith Fair. I was in one of my “I’m a little shit” periods. I’m enjoying my stardom, kind of. Not mean, but I was late for the last song a lot. I come rushing to the stage. I was doing romantic things I shouldn’t have. I was a bit of a rapscallion at that point. Not a bad one. Everybody likes me, but I was just a rapscallion. I was never happier. That was hog heaven.

But we were at, I want to say it’s Sunset Sound. There’s a basketball court and when people are not recording at the studio, people go out and they play basketball. So, I was just by myself shooting hoops. I like to hit backboard shots, so it was like thunk-thunk, thunk-thunk over and over again. And Sheryl comes tearing out to the studio hallway and opens the door and she’s like, “Who the hell is playing basketball because it’s fucking the pre-recording in the studio.” They’re trying to record. She’s a perfectionist.

She said “Liz,” [in] that Southern drawl, “Can you just not play basketball right now?” And I said yeah, of course. And then she came back out, she said, “Do you want to sing back-up on that song I’m doing right now?” I think she was at the console, so I don’t know who was producing it, but she might as well have been. I said, “Of course I do,” and I go back in and I stand with one of her bandmates and he gives me courage because we’re supposed to do this two-part harmony in the isolation booth and I’m not doing it well enough.

Sheryl said, “Try that again. You’re a little pitchy.” And I said, “Oh shit.” I know for a fact that my voice is always pitchy. We’re not going to achieve the specs that she needs. Then I’m giving him the eyeball and he’s like, “It’s going to be fine.” Then I’m like “No, it’s not.” It’s one of my favorite all-time memories and I just asked her if I could turn it into a Fairy Tale [Phair’s yet-to-be-completed follow-up to Horror Stories]. She said she’d be flattered, so I get to tell that story.

Whitechocolatespaceegg (1998)

You’ve spoken before about feeling nervous and awkward when performing in your early career. By the time you hit the Whitechocolatespaceegg era, were you feeling more comfortable as a live performer?

PHAIR: Well at that point, I was the mom of a one-and-a-half-year-old. Something glorious happened when I had my child. I don’t know if you have kids, but when you introduce them to the world, you get to see the world from new eyes. And up until I’ve been married and pregnant, which happened quickly, I took a swerve away from the music business and into more of a life that I thought when I was younger, I would want to lead. Up until that point, I had all this self-centered angst about [how] “people want something from me, and they don’t understand who I am, and the business has exploited it.” I would read my own reviews and I’d say, “That’s defaming me,” all [that] kind of shit.

And the minute you have kid, you’re like, none of that matters. I have the best job in the world. I’ve always had stage fright, but it occurred to me that my job is to sing music in front of appreciative, clapping people and what the fuck is so bad about that?

So, I was in a pretty good frame of mind to re-embrace my career. I hadn’t been thrown into my next industry cataclysm, so it was a nice moment of feeling like the Lilith Fair opportunity changed how I saw the music business, because being around so many women rather than being a minority female in a huge group of intimidating men, we were the norm.

A couple of things opened me back up to life and happiness and embracing of my opportunities and success.

Liz Phair (2003)

Did that mindset trickle down into your follow-up album, 2003’s self-titled?

PHAIR: It did. With 1998’s release, Whitechocolatespaceegg, that was a collaboration. I guess there’s no way for me to do this interview without explaining the business context because it’s a lot of what’s going on in my life. So [up until then], I was just on Matador. Then there was a thing going on in a larger music business where indie was getting folded into major labels. Indie had become so successful, with Nirvana and all of that stuff, but majors either felt that was an opportunity or they felt [so] threatened that they wanted to buy them up.

At first, it was Atlantic. I think Whip-Smart came out on Atlantic and Matador, or something like that. And then Matador went to Capitol and we worked Whitechocolatespaceegg with Capitol and a major label that I was unfamiliar with, and Matador, which was a really herky-jerky process and semi-successful behind the scenes. It just was too many people. All that did was giving me 12 more people I had to talk to on top of the people I was already talking to, who had different aims themselves. They were having disagreements. It was just too fucking much.

But there was a sense of growth. Matador’s trying to find a way up, getting better numbers, and I’m hopping along for the ride. There’s a sense of okay, well this is a great job and I’m well-positioned to take advantage of it. I’m an adult. I’m ready to feel masterful instead of like the caboose of the train. I hate when I’m at the caboose and everyone’s driving my career at this way and that. I’m just whipping around at the back. So, I stepped into more of [a mindset like], “Let’s grow.” It’s a natural time, like 31, 32.

So that does [fit] nicely going into the eponymous record. Except for the fact that Matador left their agreement with Capitol, but Capitol retained only me. All of a sudden, all these people I’ve worked with the whole time, that had a similar sensibility to me, were gone, and I was just alone on a major, which was frightening, overwhelming. I felt a pressure in the early Aughts. I’m watching these huge, multi-person pop manufactured bands ascending, and I don’t have my indie-cool group to tell me how to do this or where to go, what to do.

[Capitol Records CEO] Andy Slater felt that. He said, “I’m giving you a shot and if you don’t take the shot, there’s nothing much I can do for you.”

Yeah, no pressure or anything.

PHAIR: No pressure. And now that I’m divorced… So, I’d gotten divorced because I took too many normalcy items in my life. I overwhelmed myself with normalcy too quickly and I’m feeling lost in my personal life as well as lost in my career, and so I just leaned it. I said, fuck it. I’m on a major, everything is big business.

The record that I made with [singer/songwriter] Michael Penn had great moments in it, but it didn’t really feel like mine, and that was something that Andy Slater put together. So, I just needed more room to be myself and the way I bought that for myself was by doing the pop songs which, when I did them, I don’t know. Am I still in the question or am I just rambling?

Definitely still with you.

PHAIR: When I did the pop songs, I went to see the big, bad pop makers. Just on Avril Lavigne [records] and I was like —

Right, the Matrix songwriting team?

PHAIR: The Matrix. Yeah.

My experience in my career is so different than fans’ experience of my career. They just get what the label puts out. They just get the spin and the press. They get all this sanitized or over-simplified version, and I think there are huge gaps that are missing in terms of bringing the fans [into it].

I try so much better to bring the fans along the journey with me on social media. So, my experience with the Liz Phair record was actually challenging, but good. I grew a lot as a performer. I did something I was scared to do, like finding my path in a whole new [way]. It’s like moving to a new city and making new friends and trying to be a different person.

“Why Can’t I?” In 13 Going On 30 (2004)

Well, I have to admit that my first introduction to you was through the eponymous record, because of your “Why Can’t I?” song placement in 13 Going On 30. I still love that song placement — it’s in my top five.

PHAIR: It’s one of the things I’m most happy about. Whenever it comes on, I stop to watch it and wait for my song. I love that movie. Jennifer Garner is so great in it and so is… The Italian guy, what’s his name?

Mark Ruffalo?

PHAIR: Yes. It’s just really well-written and perfect for the pop-record sensibility. I think it gave me more legs in my career because a whole group of 13-year-olds, no joke, 12- and 13-year-olds who just adore that movie, hold that song in such reverence, as do I.

Being In An Apple Commercial (2001)

While we’re still talking about the early aughts: I found an Apple commercial you were in, from 2001. You’re on a stage with people like George Clinton, Barry White, and Smash Mouth. Do you remember this?

I remember absolutely everything about that shoot. I remember it top-to-bottom because it was really a fun moment. It’s always exciting to be around other artists like that. If you’re nominated for a Grammy, you get to rub shoulders, or if you get to go to a post-Oscars party, that kind of stuff.

When I got to the make-up place, Lil’ Kim was in the seat near me, just over. So, she’s been already in hair and makeup and she was the last person to get onstage. When she came, it was like she was sprinkled in fairy dust. A bunch of people came to arrange her and set her up on her stool fervently and I was like, God damn it. I think I just got some mascara and lipstick and they’re like, “You’re good.”

There was another moment which was super awkward. I remember trying to stand near Sigur Rós. I wanted to stand near them because I got their music and I thought they were the super-cool artists that I wanted to be associated with at the time.

Also, I remember with total mortification that the director kept telling George Clinton how to say “funk.”

That’s so messed up!

PHAIR: And it went on for four tries and George is just looking at this guy and he’s willing to play ball, ‘cause he just wants to do the job, and we all think Apple’s a good product. But the director was like, “No, can you just say it like ‘the funk’? The funk?’” And I’m just watching this white director tell fucking George Clinton that he’s not saying “funk” [correctly], and I’m just like, oh my fucking God.

And then there was even more gossip after the shoot because Barry White was in the back in this double-breasted navy blazer looking like he snuck off a yacht or something. I think he had a captain’s hat on, I’m not even kidding. I can’t even say this is true, but this is the rumor. We each were given a private car to get to and from the shoot. Barry White took his fucking car and driver to Vegas and didn’t come back for like two days!

That is truly legendary.

PHAIR: Epic. I live for these moments.

Playing Herself On Charmed (2005)

Speaking of you showing up on TV, do you recall your guest spot in Charmed? I think you’re playing yourself?

PHAIR: It was one of those things that happened very fast and I didn’t absorb the experience of being there. But it paid out for years to come. I’ve got a whole new group of fans from being on Charmed, but the occasion itself is a blur.

I always feel really weird when I’m playing myself on a TV show. I prefer to be in a character because my brain short circuits to be on stage anyway. There’s a part of me that’s already split in half. It’s like Voldemort with his horcruxes. I’ve already split myself in half to actually go on stage at all, but then to split that half into another half to be pretending to be in a fictional space playing myself, it literally is like my brain can’t make the leap. So anytime I’ve been a performer in a fictitious TV show, you can look at my face and I will look definitely lost and confused or fakey because I’m just like, “What’s happening.”

There’s a part of my voice that will not shut up. My inner voice, my inner head. What’s happening, what’s going on, what is happening, who am I because I’m already one step removed from who I think I am and then I’m one more step removed from who that is. But then, boy do I get appreciation from the Charmed fans forevermore. That’s really touching to me. Their loyalty to that show. The fact that it was female subject and embracing the narrative of witches as good things, this powerful thing.

I think I used to get scared to say it publicly still, [but] when I was little, I thought I was a witch, and I still have witchy tendencies. But I’m still afraid because I think they’ll burn me at the stake or something. Just like my son doesn’t want to go on my social media. He’s been adamant about not being part of my social media for as long as I can remember, and he’s like, “Someday I might have a career and that will come to haunt me.” And I’m like, “Really, eight-year-old?” But I feel that way about acknowledging my witchiness, because it’s like I can’t go on the record with that.

Well, this is a safe space for witchiness. I used to befriend the girls who called themselves witches in middle school because they were more interesting to hang out with.

Star Wars Cantina Band Audition College Humor Sketch (2014)

Anyway, would you say you felt more comfortable playing “a character” in this 2014 Star Wars cantina band audition sketch from College Humor?

PHAIR: No, I was totally uncomfortable. I was completely freaking out. I wrote this little song for it, which I enjoyed doing. I enjoyed writing the song for the concept, but when I was there, I don’t know what it is. I get really short-circuited. I might be some spectrum-y brain. The older I get, the more I think I might be somewhere in that weird something. Something is definitely different about my brain that most of the people that I know, I guess. You know how people have to shout the elephant in the room.

I was being Liz Phair, but I was being Liz Phair in a made-up world. And then I wasn’t even playing Liz Phair, I was playing some Cantina performer. And I remember just thinking, I come out of a period of writing and being at home and composing [for] TV, so I wasn’t used to the camera, and I was sitting in the makeup chair and I looked at my face and I had let my eyebrows go. I hadn’t gotten facials or done anything. My hair was all unruly, and I looked at the makeup guy and he’s like [makes a tsk-ing sound]. I didn’t realize this is what I looked like. I’ve been writing, I’ve been at home. And he goes yeah, “You forgot how to look. I know that feeling. Don’t worry, we’ll take care of you.”

The Body Rocks (2010)

And earlier in the 2010s, you did kids’ music with Minnie Driver and Doc Dauer. How did it feel to lean into music for the youngest set?

I guess that’s what the I’ve Got The File On You is, because it’s all the weirdo moments I’ve been through. This was a weirdo moment. Again, when I was scoring television, Doc was one of my partners in that. So he and I were friends, that was very comfortable. I knew Minnie Driver a little bit from various friends like Pete Yorn and Doc. I think she’s a beautiful singer. So, recording for the kids’ album, [The Body Rocks], in the studio was so much fun. I’m very proud of all the backing vocals. I designed all those backing vocals.

I always feel the same about pretending to be me, pretending to be someone else. And so the whole experience was a surreal… I’m always trying to find myself in a situation like that. I wish I were more of a performer mentality who just says, “Use me, use my voice, use my charisma in any way you wish,” but I’m more: “I mean to say this, this is authentically what I feel, what is all this extra stuff, what is my role in all this, what is my role in this melee of pop cultural something.” You know what I mean? I have trouble finding myself in it.

Playing A Bitchy Office Manager In Cherish (2002)

PHAIR: The best I ever felt, which I guess you didn’t find, was my role in Cherish.

I did not find it!

PHAIR: When I was a bitchy office manager, I didn’t have a guitar. I wasn’t pretending to be Liz Phair pretending to be Liz Phair. I was actually a character and I was so much happier. I was like yes, I’m the bitchy office manager.

Clearly, I have some more digging to do in your IMDB.

That was from Robin Tunney. Actually, Robin Tunney, she dated one of my brother’s friends back in Chicago when she was in high school. So, she’d actually come to my house, and I didn’t remember it. She said I was really intimidating. I was wearing black combat boots. We ended up becoming friends and we took vacations together.

She said, “Come with me in my movie and you get to play this person.” I remember this advice she gave me right before one of the scenes with Jason Priestley. She goes, “The camera picks up subtlety more than you think, so you don’t have to exaggerate your face.” In music, on stage, you’re supposed to do the opposite. Big expressions and stuff.

Funstyle (2010)

For a lot of people, Soberish is the first studio album they’ll have heard since Funstyle. What’s your take on how the discourse around Funstyle has evolved since 2010?

PHAIR: Well, my take is that’s not a studio album. The last studio album I did, a real studio album, was probably… You’re not going to believe this. This is going to shock the world but probably Whitechocolatespaceegg.

The eponymous album was a compilation of various recording situations that I would do with my live band just to get material, almost like demos for the record. And then I did do a studio album with Michael Penn that I took three or four songs from, but then I also did the pop stuff. I was going into other people’s studios or casually [record] with my live touring band. The only studio work I did was with Michael Penn, which I only took three or four songs of that for that. So, that wasn’t me crafting an album for you guys, and neither was Funstyle.

Funstyle was literally rummaging through my closet of outtakes and then doing some weird sound design shit with my other TV scoring partner, Evan Frankfort, that we would do when we were just fucking around. In between scoring TV, we’d start to make songs and start laughing our ass off.

But my disconnect is, I never understand my life versus what people experience me as in a fan space. Soberish is the first proper, thought-through, totally crafted album since Whitechocolatespaceegg.

Soberish (2021)

That makes sense, then, that you would be working with Brad Wood. That feels like a true continuation. Your press materials really try to promote the fact that Soberish is a Liz Phair Revisits Her Original Sound sort of album. Does that feel true?

PHAIR: It’s very true. I don’t think I could have stepped back into the studio without putting out that box set [2018’s Girly-Sound To Guyville anniversary albums] through Matador and going back. The box set came out. I’m so proud of that. I’m so happy with the way it turned out. I think Matador did a brilliant job, but it was a three-year process of literally asking people to go into their storage lockers and like, do you have any usable cassettes? What is the sound quality? Can we master that? Do you have any old pictures that haven’t been shown?

It felt really complete. I feel everything that needs to be said about that era, from my point of view, is in that box set and I’m so grateful for it. It just feels like such a gift, and I was skeptical of it. I remember the first meeting with Matador in New York. Peter Katsis, my manager, came with me and they’re like, I think we should put all the Girly-Sound cassettes, and I’m like, you really think people are going to buy that? I was just skeptical. I’m like, what’s the point of that?

They said no, I think it’ll be wonderful. And it turned out to be better than I could’ve expected. It wrapped up a confusing, exciting, successful but also troubling period in my life in a way that seduced me back into myself. And I don’t think it’s any surprise that I’ve made my first real studio album in 20-some years, because of the box set.

And you were intentionally leaning back into that proto-Phair, indie-rock aesthetic?

PHAIR: 100%. We wanted to use the sounds of Guyville, like, the plug-ins, the microphones, the alphabet, if you will, of Guyville, but then write a new language. And I really asked Brad, I challenged both of us, to step into what my experience of Guyville was, which was these sounds, these building blocks, these familiar tools. But then my experience with Guyville was the first time I’ve ever been in a studio, and the surprise of it all, not knowing where we were going with things. Letting the song lead us somewhere we never imagined taking it. That was how I experienced Guyville.

I have to tell you how much I appreciated the ultra-honest language around divorce in “Spanish Doors,” as someone who has personally gone through that.

PHAIR: I’m so glad. I’m so glad that connected and I’m so sorry that you have to go through that. I feel most of us will encounter that. It’s like someone took a knife through your whole life and left you almost a cross section, just open and bleeding for multiple wounds. Even if you’re the one leaving, it’s still a few inches sliced right through your life and everyone else have their crusts and edges all around for protection and you’re just suddenly cut open with all the innards showing, just oozing.