Back when indie rock was beginning to brew, singer-songwriter Liz Phair emerged as a bold, feminist pioneer in the developing scene. Unafraid to overshare or express her anger, Phair gained a following for her unruly and uncompromising attitude. Her music’s popularity alongside like-minded musicians like Fiona Apple and Aimee Mann is something that landed her at Lilith Fair during its run. Her raw songwriting about one-night stands and coming of age has made her one of the strongest alt-rock musicians of the ‘90s. As times and stereotypes have changed, its significance in culture has continued to carry weight over the past 20 years.

Phair released three albums in the ’90s that made her stand out as an emerging female voice in the lo-fi, alt-rock scene, but it was really 1993’s Exile In Guyville that launched her career. It was a critics favorite — both Spin and the Village Voice Pazz & Jop rated it as the number one album of the year — and to this day, the record consistently makes it onto “Best Of” lists.

People who were fans of Phair’s from the start expected her to stay angsty, rebellious, and indie, but Phair didn’t have the same vision. Phair made Exile In Guyville and 1994’s Whip-Smart while female-fronted alt-rock was at its height, but as the tides changed and the masses became more focused on pop, so too did Phair. A move into the pop world was first noticeable on her 1998 album, Whitechocolatespaceegg — a direction that would confound critics and fans alike.

Five years later, Phair would release her first pop-flavored record after working with the Matrix, the songwriting team with whom Avril Lavigne worked on her 2002 debut, Let Go. Fans didn’t seem to love that Phair wanted to be a part of the mainstream music community. Rock in the ’90s craved authentic, raw songwriting, while the ’00s introduced acts like Lavigne, who looked and acted vaguely countercultural, but were undeniable major label pop acts. Phair fell somewhere in between those two modes, so her collaboration with Lavigne’s team made sense. Phair’s self-titled album did help her to reach a broader listener base, but her loyal fans weren’t so keen on the idea of a pop album. Liz Phair featured clean production and resulted in a radio hit thanks to the lovesick anthem “Why Can’t I?“. Two years after that, Phair would release Somebody’s Miracle — a collection of songs that seemed to aim to rekindle her original fanbase with stripped-down, more folk-oriented songs. Her next (and most recent) release came in the form of 2010’s Funstyle, which took Phair’s talents in a whole new direction, fusing funk with rap tracks. It’s something that didn’t suit Phair’s talent and was considered a failure among critics, though she stated that it was a concept album.

Since her 2010 experiment, Phair hasn’t released any new music. However, she’s joined the Smashing Pumpkins on that band’s current tour, and has been playing a new song titled “Our Dog Days Behind Us.” Hopefully the break in between records has found her comfortable in her voice once again (and maybe not rapping).

10. “Extraordinary” (from Liz Phair, 2003)

Self-empowerment is something Liz Phair has never strayed from, and on her self-titled album, it’s something that’s magnified, especially on “Extraordinary.” While the meaning is quite transparent — Phair has fallen for someone who doesn’t seem to see all the great qualities about her — it’s a song that flaunts confidence and embraces character flaws. Phair is an “average everyday sane psycho super goddess.” While the lyrics of “Extraordinary” aren’t quite as wrapped in the metaphors that were seen on her earlier records, they still promote Phair’s brand of feminism as she preaches what every woman should tell herself: “I am extraordinary, if you ever get to know me.”

9. “Lost Tonight” (from Somebody’s Miracle, 2005)

It’s a miracle that “Lost Tonight” was on Phair’s 2005 album, because most of Somebody’s Miracle was full of faux jingles (“Stars And Planets”) and cringe-worthy songs that feature her singing out of her vocal range (“Wind And The Mountain”). After Phair’s self-titled foray out of Guyville into popville, she attempted to revert back to her stripped-down ways. However, most of the songs didn’t show off her vocal talent and fell in an awkward “not quite pop but maybe lite-rock” category. “Lost Tonight” is lyrically more mature and quite tame in comparison to, for instance, “Fuck And Run,” but it mirrors the early-’90s grunge ethos that launched Phair’s career.

8. “Never Said” (from Exile In Guyville, 1993)

Exile In Guyville was a coming-of-age album for Phair that addressed the oscillating sensation of feeling like a child even though you’re an adult. Through anthemic, layered vocals, Phair protests, “I never said nothing” over and over as if she were stating her case after getting in trouble in the principal’s office. She later taunts: “I’m clean as a whistle, baby.” Knowing Phair and her rebellious persona, she was probably lying, and that’s what makes you love her more.

7. “What Makes You Happy” (from Whitechocolatespaceegg, 1998)

Whitechocolatespaceegg came after a four-year musical absence, but begins right where Phair left off in lyrical candor. However, Phair’s mood seems more uplifted on the album overall, and she knows it — after Whip-Smart, she left part of her angsty self behind and got married. With an almost bluegrass-like beginning, “What Makes You Happy” reveals a sunnier perspective from Phair. Optimistic Phair is almost as likable as angry Phair. “I swear this one is going to last,” she assures. “And all those other bastards were only practice.” Her positivity shines as she sings: “I feel the sun on my back, I smell the earth on my skin.” Phair’s New Age perspective suits her well, and sets the scene for her pop debut five years later.

6. “Red Light Fever” (from Liz Phair, 2003)

“Red Light Fever” was definitely not one of the more liked tracks on Phair’s collection from 2003, when she transitioned into a more radio-friendly artist, but it’s an undeniably catchy gem that features Phair’s vocals at their most pristine. In a more obvious context, the song reads as a reflection on her own anxiety and the extreme lens through which she sees things. The visual “red” and “green” in the song are obvious motifs that highlight Phair’s own indecisiveness and the universal frustration that comes with feeling like you’re constantly “stuck in your head.” While there’s a simplicity to Phair’s lyrics on “Red Light Fever,” it’s the lulling of the song’s melody that remains hypnotizing.

5. “Girls! Girls! Girls!” (from Exile In Guyville, 1993)

The opening of “Girls! Girls! Girls!” has the same dark, striking effect as that of the Breeders’ “Cannonball.” “Girls! Girls! Girls!” serves as both a response to previous track “Fuck And Run” and as an interlude to the moodier half of Exile In Guyville. Instead of questioning her self-respect as she does on “Fuck And Run,” Phair owns her sexuality and decision to have one-night stands. “You better let me go,” she states, “because I take full advantage of every man I meet.” Phair’s enlightened perspective of promiscuity also finds her looking at the world from a man’s perspective, which she appropriates in the title. The suspense created by the song from the get-go leaves you waiting for change on the second half of the album.

4. “Polyester Bride” (from Whitechocolatespaceegg, 1998)

Four years after releasing her sophomore album Whip-Smart, Phair emerged with Whitechocolatespaceegg — an LP that featured pop-tinged tracks straying from the singer’s gritty beginnings. But “Polyester Bride” shows Phair looking back at her defiant younger self through characterization. “Do you want to be a polyester bride?” she asks herself. “Or do you want to hang your head and die?” The track came out three years after Phair was married and perhaps foreshadows the fact that her future wasn’t so set in stone. “Polyester Bride” still shows off the imperfections in Phair’s music as she sweetly hits the high notes, singing “fly away from here” on repeat. If there’s anything that Whitechocolatespaceegg can show listeners, it’s that Phair’s transition to pop was gradual and natural.

3. “Why Can’t I?” (from Liz Phair, 2003)

While many of Phair’s early fans sneer at her transition from grunge-inflected indie rock to pop, her self-titled album was actually a natural growth from her rock roots. With the help of the Matrix, “Why Can’t I?” was penned as an appealing pop track that was perfect for mainstream radio play. This was a stark contrast to the songwriting process for her previous records. For longtime Phair fans, “Why Can’t I?” and her self-titled album seemed to show her “selling out,” but Phair was always open about her desire to move in more of a mainstream direction. While the production was smoother and lacked the rough-around-the-edges feel of Exile In Guyville, Whip-Smart, and Whitechocolatespaceegg, Phair still intimately sings about love and relationships with the same candor that she did earlier in her career. But this time, it’s about a forbidden romance between two people with respective significant others. “Holding hands with you when we’re out at night, got a girlfriend, you say it isn’t right, and I’ve got someone waiting too.” There’s no shame in the success of a catchy pop song, and Phair achieved that with “Why Can’t I?”.

2. “Supernova” (from Whip-Smart, 1994)

Following the success of Exile In Guyville, “Supernova” gave Phair her first taste of radio play. The song’s hooky, alt-pop charm was undeniable and put her at the forefront of the lo-fi indie rock scene of the ’90s. On “Supernova,” Phair unapologetically compares sex with a dude to one of the galaxy’s great wonders: “Your kisses are as wicked as an F-16, and you fuck like a volcano.” While Alanis Morissette gets a ton of credit for talking about her sexual escapades in “You Oughta Know,” 1994’s “Supernova” reveals Phair as a true pioneer of women being unafraid to rawly talk about their sexuality through music. In fact, she even compares a guy’s lips to a “cherub’s bare wet ass,” an image that is impossible to remove from your brain.

1. “Fuck And Run” (from Exile In Guyville, 1993)

“Fuck And Run” is the quintessential Phair single; it represents her ethos. On her best track, she embraces her own sexuality, self-respect, and position as a feminist — something that carried her through the better part of her career. Phair reveals the reality of never-ending one-night stands (“It’s fuck and run, fuck and run, even when I was 17″) and questions her own standards and self-worth (“And whatever happened to a boyfriend, the kind of guy who makes love ’cause he’s in it?”). “Fuck And Run” was largely the catalyst for the success of Phair’s first record — thanks to the song’s brutal honesty and raunchy lyrics. Girls from the ages of 15 to 24 will always find solace in the fact that the same dating frustrations existed 20 years ago, and Phair stood strong and survived.

Listen to the playlist on Spotify.