6. “Why Can’t I?” (2003)
Speaking of which, let’s get it out of the way: “Why Can’t I?” is not one of Phair’s best songs. As underrated as some of her later material is, “Why Can’t I?” can’t really compete with most of the songs on her first three records. Yet her biggest hit is worth hearing and a weirdly essential component of any Liz Phair overview. It comes from her self-titled 2003 album, one of four songs produced by the then-trendy, now-semi-obscure mini-collective known as The Matrix. Their studio sheen involved an overpolished guitar sound, lots of echoed lines designed to fit in de facto extra choruses, and sometimes backing vocals from Matrix member (and former singer-songwriter) Lauren Christy. “Why Can’t I?” indulges most of these tics, but it also retains Phair’s authorial voice more clearly than the other Matrix-produced tracks. “We haven’t fucked yet but my head’s spinning,” for example, sounds more like classic Phair than any of the idiotic rewrites of Meredith Brooks’ “Bitch” that characterize the far worse “Extraordinary” (which has joined “Why Can’t I?” as a regular fixture in Phair’s set lists years later). The heedlessness of the love affair Phair describes here almost justifies the plastic-summer production. Also, credit where it’s due: “Why Can’t I?” is catchy.
7. “6’1”” (1993)
An expert album-opener by any standards, the first track from Exile On Guyville addresses issues of anger and confidence head-on. The way Phair’s voice lowers a little when she says “six feet one, instead of five feet two” wouldn’t be reproduced on her later records, and maybe that’s a good thing: It feels spontaneous and genuine, not the kind of vocal tic that she should be self-consciously repeating.
8. “May Queen” (1994)
Because Phair receives so much attention for her lyrics, sometimes her sense of melody and vocal phrasing get overlooked. “May Queen,” for example, is somewhat obtuse and spare lyrically. The most-emphasized lines are the scattered-sounding questions: “Where have I been? Got any what?” But the way she hits that second question makes it sound declarative and definitive, rather than hazy.
9. “Firewalker” (2003)
Liz Phair got a lot of attention for its Matrix-produced attempts at Top 40 drivel, and the ensuing indie furor overlooked just how grab-baggy that record is. Aside from the few Matrix-produced songs, several others wouldn’t have been out of place on a more direct Whitechocolatespaceegg follow-up. “Firewalker” is one of them. It makes sense that this song had been kicking around since at least 1999, and versions from shows around that time don’t differ much from the final version, with a lovely vocal melody on the chorus that sounds like the thinking person’s Sheryl Crow. “You might not recognize me tomorrow,” she sings, signaling (intentionally or not) what a lot of fans would consider a major change in direction.
10. “Table For One” (2005)
This Somebody’s Miracle highlight about alcoholism was written by Phair from a male point of view (“I still see that guy in my memory,” the narrator laments about the man he used to be), describing the quotidian aspects of his disease in gently heartbreaking detail. She’s mentioned in interviews that this song is based on the experiences of her brother, and its deep currents of empathy speak to her skill as a writer. If there’s one post-’90s Liz Phair song more people should hear, it’s this one.
11. “You Should Know Me” (2010)
Later-period Liz Phair albums are undeniably scattershot, none moreso than Funstyle, which like the self-titled album, received more attention for its worst outlier tracks (Liz raps and makes lame jokes!) than its several excellent but less aggressively ear-grabbing (or critic-baiting) efforts. The album was rejected by her new label and subsequently self-released online, then eventually put to disc with a bonus set of old songs from her legendary Girly Sound demos. This release effort further obscures the strength of songs like “You Should Know Me,” a not-quite-breakup song that, like a lot of her most underrated songs, explores the nuance between the giddy love she sings about on Liz Phair and the crashing and burning she narrates on her early records. Her description of how “your closing eyes turn away from me” and sad lament that “you should know me better than that” float over a slightly tentative melody, a vulnerable flip side to the bravado of other Funstyle tracks.
12. “Little Digger” (2003)
“My mother is mine,” says the narrator’s young son to his mother’s houseguest in “Little Digger,” which even most of Liz Phair’s harshest critics agreed was a highlight. It’s a sharp sketch of a moment that “changes how things have always been,” as a child of divorce attempts to assert himself as his mom’s most important person. For someone who built her reputation on a certain single-gal wildness, in “Little Digger” Phair brings dimension to the often-messy process of domestication.
13. “Uncle Alvarez” (1998)
A lot of Phair’s songs are written in first-person singular, even if they’re not autobiographical, but this first-person-plural tune describes a family black sheep who seems to have fancied himself anything but: “He’s not really part Cherokee Indian; he didn’t fight in the Civil War,” as the lyrics rebut unheard claims to fame. Maybe this is her song about notoriety or accomplishments (deemed “imaginary” here), or maybe it’s a character sketch for a character who never appears in person. It works equally well as both.
14. “And He Slayed Her” (2010)
It’s safe to assume that at least some of Phair’s most biting work has been based on real experiences, but “And He Slayed Her” is an actual revenge song (appearing alongside the more ill-advised preemptive strike of a gag song “U Hate It” on Funstyle). The title refers to Andy Slater, head of Capitol Records when Phair relocated there from Matador, and the lashing out might seem petty if Phair weren’t so good at it. She inflects a line like “I mean, what kind of kid were you when you were a kid?” with just the right conversational lilt to make it funny rather than redundant.
15. “Fuck And Run” (1993)
Phair wakes up alarmed in one of her more notorious and essential Exile tunes, which has her fighting against and giving into a penchant for one-night stands. Cleverly, the provocation doesn’t really come from the title phrase—frank, but to the point—but rather the way she chases it: first with “even when I was 17” and then adding the more chilling “even when I was 12.” Underneath the provocation of those lines, though, is concise storytelling that should make prose writers everywhere jealous.
16. “Polyester Bride” (1998)
In a way, this is Phair’s dry run for “Why Can’t I?”: The first single from Whitechocolatespaceegg is one of her poppiest, sweetest melodies, driven by a churning acoustic guitar riff, but it never ascended beyond minor-alt-rock-hit status at best. In a better world, this is the Liz Phair song non-fans have heard, a wry (and vaguely whimsical) consideration of privilege, courtesy of a bartender she is, as he points out, lucky to know. Rerecorded from a slower, lower, more tired version from the Girly Sound tapes, the album version sparkles like alligator cowboy boots they just put on sale.
17. “Go West” (1994)
To make up for “Go West” not taking its natural place as the final song on Whip-Smart (that honor goes to the equally wonderful “May Queen,” a less intuitive but perhaps more inspired choice), please affix it to the end of mix tapes (or, if you will, playlists) until the end of time. Featuring Phair at her breathiest, this song describes the bittersweet moments just before a new beginning as the narrator practically sighs over her obligation to move forward. Judging from her output since 1993, this has not been a problem for Liz Phair.