Since listening to some of these songs in the car with you on the way to grandma’s for Christmas and realizing you were less familiar with the 90s female singer songwriter boom than I’d assumed, I’ve had it in my head to try to communicate what it was like to be a trans teenager at that precise moment. So, because I’m me, I wrote you an 8000 word essay/annotated playlist and am posting it on your birthday. So happy birthday. There aren’t a ton of rules for this; it’s all female vocals, mostly from the 90s, though anything that came out during my life but before I graduated high school was eligible, so there’s two 80s tracks. I centered the playlist on the Lilith Fair; a touring festival of female musicians that took place from 1997-99 and that always felt to me like the nexus of the musical era I’m trying to sketch for you, although songs by non-Lilith Fair artists are included. Likewise, the songs are not always my favorites, whether from the period or now—they are chosen instead because they collectively capture a fragile strand of libidinous glamor that I hung onto for dear life as a kid.
Oh, and everybody else: Yep, it’s our very own Christine Kelley’s birthday. Don’t forget to support her work on Patreon.
1. Ani DiFranco, Untouchable Face (1996; Never Played Lilith Fair)
The central moment to remember, years later, with a vivid clarity so intense you can practically feel the upholstery, will be sitting in the passenger seat of your mother’s car outside the Borders in Farmington. By this point you are already into this sort of thing—a clear and developed fondness for the female singer-songwriter boom. You have heard of Ani DiFranco somewhere on the Internet, recognizing her as a next door neighbor to stuff you already like, and so on your next shopping trip you spend your allowance on Dilate. You head out to the car with your mother, pop it into your Discman™, and give it a listen.
At first it seems familiar—a lilting guitar, a slightly melancholy vocal, wistfully nursing a breakup with a seemingly amused distance. You will understand this through the first verse. You will think you have a handle on this. And then Ani DiFranco will calmly, even sweetly, intone the first “fuck you” of the chorus.
In truth this is cringe. DiFranco is already exiting her imperial phase—you will later rehearse an argument that the precise moment her career goes off the rails is the horn part on the first track of her next album. In years to come she will play a plantation, rewrite the barnstorming pro-union “Which Side Are You On” into a piece of bland pro-Obama glurge, and generally become a middle-class parody of the DIY folk-punk icon she momentarily appeared to be. She will be a taste you embarrassedly defend to Lexi, until she grudgingly admits that Amanda Palmer played a similar role for her.
In the moment, however, none of this matters. You will look back at this moment and discover, for the first time in your memory, that it is easier and more sensible to picture the person in the passenger seat is a girl.
2. Garbage, Only Happy When it Rains (1995; Never Played Lilith Fair)
Garbage is an old and established structure for bands: a bunch of boys find a frontwoman. Done right, with sufficient deference to the frontwoman’s creative input and vision, this is historically infallible. Garbage is a case in point: an all-star class of backing musicians headed up by the guy who produced Nevermind, but the centerpiece of the band, its heart and soul, was lead singer Shirley Manson.
Manson—blessed at birth with a name so perfect that Brian Warner would toil to recreate its glories—was a snarling post-grunge diva; a glorious recorrection towards glamor and, more crucially, eyeshadow that heralds the goth resurgence that will characterize the decade’s end. The video will be totemic for you, and for a brief period you will even favor MTV over your usual VH1 because they play it more. You will stare in rapt and clearly erotic fascination as she oscillates between pink and blue versions of an ecstatically short dress over fishnets and the sorts of boots you will spend the rest of your life wishing you could pull off.
In hindsight you will recognize this as the “do I want to fuck her or be her” question—one that’s hard enough to answer when you’re actually aware of being a girl, and doubly so because the answer is never so convenient as to just be one thing. For now it is sufficient to long, whether or not you know what you are longing for.
3. Sinead O’Connor, Jackie (1987; Played 1998 Lilith Fair)
You will only ever be aware that Sinead O’Connor exists, and dimly aware of her cancellation. But for all that she was among the biggest artists in the world at the beginning of the decade, O’Connor was simply erased from the cultural landscape of your 90s adolescence. Like any erasure, of course, traces remained. “Nothing Compares 2 U” would make occasional appearances on VH1, where it bored you—a reaction that will never really change no matter how much you listen to the song. And in the early days of the Internet her scandalous 1992 Saturday Night Live appearance—the reason why she was excised from the culture—would filter into your awareness as you went down the various rabbit holes of special interest. It will not be until adulthood that you would come to appreciate her bravery in tearing up a photo of John Paul II, the horror of the Catholic Church’s coverups of sex abuse, or the titanic unjustness of her cancellation, including what has to be a strong contender for the single most craven act of Madonna’s artistic career. More to the point, it will not be until adulthood that you appreciated that she fucking slapped.
“Jackie” is a song that will fit seamlessly into future iPod DJ sessions, slipping perfectly between Siouxsie and the Banshees and The Cure, with O’Connor playing the ghostly siren haunting the shore in mad and fruitless obsession—the delivery on “you’re all wrong I said” is positively chilling. More over the top than the work she will be best known for, what stands out is the gulf between how completely unhinged O’Connor sounds and how tight and controlled her performance actually is—a metaphor for O’Connor herself, cast forever as “too much,” the mentally ill and tempestuous woman who would be eternally faulted for failing to live up to the expectations projected onto her even as she moved through life with an eccentricity that was far more meticulous than it appeared,
4. Sarah McLachlan, Possession (1993; Founded Lilith Fair)
You will never actually go to Lilith Fair. You will want to. It will cross through Hartford every year, and you will make clear your desire, but you will never go, only ever watching this cultural nexus of what you love from a wistful distance that, if we’re being honest, is actually more fitting for your relationship with femininity than participation as an apparent boy could ever be.
As for McLachlan herself, you will find yourself ambivalent, torn between your instinctive disdain for the liberal girlboss branding she will eventually settle into and the fact that “Building a Mystery” is self-evidently one of the greatest goth songs ever recorded, teeming with a luminous darkness that will transfix you every single time you hear it. In time you will, not entirely fairly, come to view the narrative of her career as a selling out, learning about how she broke out on Nettwerk, her first album produced by a guy better known for work on industrial music, a fact that brings this more ominous sensibility into the forefront as a road less traveled—one ultimately far more interesting than the way she would actually go. “Building a Mystery” was in effect its last gasp—a semi-cynical attempt to score a crossover hit when she needed one to launch Lilith Fair. (“Sweet Surrender,” off the same album, is blatantly the other candidate for this; contrast with “Aida” and “Angel,” the other two big songs on Surfacing, the latter of which is a borderline Celine Dion riff.)
“Possession” off her breakout album “Fumbling Towards Ecstasy,” is the sort of last gasp of this, before she pivoted towards the prom night glurge with “I Will Remember You,” which you will stubbornly love forever because your middle school crush who never quite reciprocated deigned to dance with you to it at the 8th grade “moving up” dance. Its lyrics, drawn from letters McLachlan received from stalkers, thrum with unsettling sexuality, an eroticism tinged with a genuine menace. The drums kicking in right as things turn into a choking scene contains yet more truths you are simply not ready for yet.
5. Dar Williams, When I Was a Boy (1993; Played 1997 Lilith Fair)
Here. Let us adjust back to what you actually listened to. You will get into Dar Williams at CTY; nerd summer camp, attended for four years starting after seventh grade, and where you will find the bulk of your dating prospects, all of whom you will be an absolute ass to in one way or another. The way in is her second album, Mortal City, which opens with one of the poppiest didgeridoo lines in music history, but you’ll eventually get the other albums. The End of Summer, her third, and the most recent when you start listening to her will be one of the staples of your early driving days along with the Ani DiFranco/Utah Phillips collab The Past Didn’t Go Anywhere and a handful of other albums you owned on cassette.
It is this sort of music that created the initial familiarity of Ani DiFranco, although she and Williams existed in diametrically opposed portions of the folk scene (well, sort of; DiFranco would eventually duet with Williams on an unsettling cover of “Comfortably Numb”), with DiFranco plugged into the punk scene, while Williams will serve as a gateway to the modern alt-folk scene, leading you to the Nields, Lucy Kaplansky and Carter and Tracy Grammer, along with Richard Shindell, John Gorka, and Vance Gilbert. This will be an enduring stopover in your musical taste; the first scene you are meaningfully attach to.
This song, the lead track on her debut The Honesty Room, captures the whole of Williams; on the one hand it is unquestionably twee—the “when I was a girl” verse is structurally correct songwriting, a fact that makes it even more obnoxious, the way that following the Save the Cat beat sheet makes Everything Everywhere All At Once obnoxious. On the other, however, with the hindsight of adulthood, and more to the point actual transition, this song hums with a libidinous and obvious thrill—in hindsight clearly adapted with songwriter class precision from “Running Up That Hill.” At the time you will listen to this and think how comforting it is that there are girls who wish they were boys too. That must just be the normal order of things.
6. Emmylou Harris, Wrecking Ball (1995; Played 1997-98 Lilith Fairs)
The baseline of the Lilith Fair was the female singer-songwriter boom of the period; there’s a whole host of other artists who played the festival and were in the same broad aesthetic space that I’ve not included here: Jewel, Paula Cole, Shawn Colvin, Joan Osborne, Mary Chapin Carpenter, Sheryl Crow, and Natalie Merchant, to pick ones who have songs you will love in the course of adolescence1. In other words, it was mostly acoustic-leaning post-folk/country pop. Inevitably, such a movement will pay off its roots—think of the way in which Bowie, from 1995-97, got to be an elder statesman for a certain slice of alternative rock. Numerous candidates for the equivalent role for the Lilith Fair existed, but in practice it would be Emmylou Harris that took on the job.
Much of this was being in the right place at the right time. A titan of 1970s country, Harris entered the 90s aware of the shifting sands in the country market—a move away from the old legends and towards the Garth Brooks generation. And so Harris pivoted, linking up with Daniel Lanois (who had worked with Eno producing The Joshua Tree and Achtung Baby, and would go on to do Time Out of Mind with Dylan) and releasing Wrecking Ball in 1995. This followed what would eventually become a relatively standard paradigm for a supposedly past-their-prime artist to make a comeback: do something serious, reflective, and a little bit off-genre. More to the point, it was a critical hit and a crossover success, doing better on alternative radio than country radio, and placing Harris in direct conversation with the Lilith Fair crowd.
The title track is a Neil Young cover, and displays the folk scene’s characteristic valuation of lyrical deftness—”meet me at the wrecking ball / I’ll wear something pretty and white” is, in fact, an absolutely stunning line that does an impeccable pirouette on the meaning of “wrecking ball.” But what’s really notable is the modification of Young’s original line, which omitted the “I’ll” in favor of the imperative. The result is one of the most subtly impressive gender flips in pop music, turning the song into a piece of yearning self-destructiveness that’s more mature in its conception than anything else on this playlist.
You will not be aware of this song in your adolescence, and more than anything else on this playlist, you will resent that loss.
7. Melissa Etheridge, I Want to Come Over (1995; Never Played Lilith Fair)
The single most important thing to realize about this song is that it made it to 22nd on the Billboard Hot 100, while the album made it to 6th. Melissa Etheridge was an entirely mainstream rock phenomenon, holding down the entirely sensible category of “chick Springsteen” until 1993, when she came out as a lesbian and released the cheekily titled Yes I Am. Between Etheridge being a musical one trick pony and the fact that she occupied such a mainstream role in lesbian acceptance (in the big coming out episode of Ellen, it’s Etheridge who delivers the final gag of giving Ellen’s new girlfriend a toaster for successfully recruiting her) it is easy to overlook her. At the time you’ll only really go for big three songs. Two of these are off of Yes I Am: the yearningly anthemic “Come To My Window” and the more fascinatingly textured “I’m the Only One” (you will get in trouble for idly writing the “go on and hold her til the screaming is gone” bit in the margins of a chemistry test when the most homophobic teacher in your school demands a meeting with your parents as evidence you don’t need a disability accommodation for your handwriting; you’d been thinking of your self-injuring girlfriend who later decided she was a lesbian). Both are overtly queer songs with a particular obsession over shame—note the lyric “I don’t care what they think / I don’t care what they say / What do they know / About this love anyway?” in the former, and “It’s only fear that makes you run / The demons that you’re hiding from” in the latter.
And then there’s “I Want to Come Over,” off her followup album Your Little Secret, and a song that single-handedly sells is far more comprehensively queer. As the album’s title suggests, Etheridge is fascinated here by the ugly yet strangely erotic weight of the closet, of love being a source of shame to be hidden. The lyrics veer with a heady and obsessive intoxication between the pained abjection of a lover desperate to be acknowledged (“I know your friend / You told her about me / She filled you with fear / Some kind of sin”) and a level of aggressive eroticism that validated every stereotype about predatory lesbians imaginable while simultaneously being absurdly hot (“I know you’re confused / I know that you’re shaken / You think we’ll be lost / Once we begin / I know you’re weak / I know that you want me / Lover don’t speak / Let me in.”).
Again, 22nd on the Billboard Hot 100. This was a major song of the time that got scads of airplay, a shockingly horny and visceral level of sapphic desire squarely in the mainstream, proving that you were never as obscure as you imagined. Frankly, there’s an awful lot of queer art from the last few years that doesn’t go nearly as far as this.
8. Liz Phair, Flower (1993, Played 1998-99 Lilith Fairs)
You will not really learn anything about Liz Phair until 2003, when she releases a self-titled album in which she willfully, petulantly sells out. (Jewel, notably, did something similar the same year, and with a similar sense of vocal and performative irony.) You will eventually defend this to Lexi, citing Phair’s lyric lamenting how a younger lover’s “record collection don’t exist / you don’t even know who Liz Phair is.” She will be unimpressed, because she is the proper sort of Liz Phair fan, which is to say someone who loves Exile in Guyville, a burst of lo-fi indie rock that you will be far too basic to fully appreciate when you buy it that summer before moving to Chicago for grad school with another eventually-lesbian girlfriend.
Still, Phair’s aggressively forward sexuality carried a clear charge. In 2003 you’ll unsurprisingly be drawn to “H.W.C.,”which combined a jaunty tune with lyrics about wanting her lover’s hot white cum on the grounds that it’s good for her skin, and which suited the edgelord tendencies of college. But its antecedent is clearly the incendiary “Flower,” virtually every lyric of which is absolutely filthy. It is difficult to wrap your head around what you would have thought of this as a teenager. You would, after all, burn yourself a mix CD called “Offend Your Parents!” that contained “Closer” and “Star Me Kitten” among others. But for all that you were up for a bit of scandalous lyricism, there is something profoundly different between Trent Reznor’s swaggering abjection in “I want to fuck you like an animal” and Liz Phair’s “You’re probably shy and introspective / That’s not part of my objective / I just want your fresh, young jimmy / Jamming, slamming, ramming in me.” The cool girl indifference here—the disaffected hornyness—does not even consider abjection as a possibility. And yet this is blatantly not sex positvity. It’s much closer to sex nihilism, with everyone involved is treated as an object. The song is wholly aware of the existence of the male listener who simply delights in the woman who openly wants to be his blowjob queen and the edgelording of it. But it consents to that objectification for no reason than that it doesn’t see that listener as anything more than a dick to fuck til it turns blue.
In a playlist full of partial knowledges you were not quite ready for in the moment, this sits entirely beyond the realm of what was understandable. As with Melissa Etheridge, what is most notable is simply that it existed—that the cultural landscape of this moment could support a song like this.
9. Jill Sobule, I Kissed a Girl (1995; Played 1997 Lilith Fair)
You will not know this song at the time, and will never be wild about it. It’s cutesy and cheap, and inasmuch as it represents queer art (and frankly it’s less queer art than queerbait) it seems to herald tenderqueer bullshit more than anything else. If nothing else, it pales in comparison with the Katy Perry song of the same name, of which Sobule complained, “It did bug me a little bit, however, when she said she came up with the idea for the title in a dream. In truth, she wrote it with a team of professional writers and was signed by the very same guy that signed me in 1995. I have not mentioned that in interviews as I don’t want to sound bitter or petty… cause, that’s not me” before concluding that “Fuck you Katy Perry, you fucking stupid, maybe ‘not good for the gays,’ title thieving, haven’t heard much else, so not quite sure if you’re talented, fucking little slut.” She walked this back a couple days later, but it still feels terribly harsh on Perry, who, having both killed a nun and never played MichFest, is fairly straightforwardly a better person than Sobule.
The truth is that the songs are more similar than Sobule would like to suggest—both lean into the “sapphic behavior as a phase” trope, using lesbianism as cheap titilllation. Sure, Sobule frames her experimentation in slightly more mature terms while Perry is playing the party girl, but that distinction is somewhere between irrelevant and more or less a restatement of the differing genres the songs belong to. And yet on some level this is their strength. Look at Etheridge or Tegan and Sara for a comparison and you get sapphic desire as a source of pain. Smoldering sexy pain, yes, but pain all the same. Putting this in between them and juxtaposed with Phair to boot does it no favors, but it does highlight the way it views gender and sexuality as a space for play, and that’s not nothing. Put another way, this was enough ahead of its time that Katy Perry and her songwriting team bothered to rip it off, which you can’t actually say for much of anything else on this playlist. But at the end of the day, all this constitutes is a clear sign that, for all that this playlist tracks the libidinous potential of this moment, it was tailor made to be co-opted. The Sarah McLachlan girlboss instincts were always going to win.
The one upside of this: the alienated, externalized way with which you relate to this material was always the correct one.
10. Tegan and Sara, Come On (1999; Played 1999 Lilith Fair)
Indie darlings at the earliest stages of their career, Tegan and Sara played the tertiary stage on the last edition of the Lilith Fair, touring to support their debut Under Feet Like Ours, an album they apparently liked little enough that their second album was 50% rerecordings of it, including another version of this song. These days they’re indie pop icons, a turn you will struggle not to be grudging about given just how much you like their pop-punk sensibilities when they’re on fire. But crucially, all of this is the future; 21st century concerns. Here, they’re some newly sprung indie artists rounding out the bill—a minor footnote turned into a novel unto themselves.
Which is to say that you’ll miss this until grad school, when a cute girl studying fanvids who you don’t yet have the language or gender to describe your queer platonic relationship with shows you a Buffy vid featuring “Come On,” sparking a mild obsession with it. It is, obviously, a cousin to the Melissa Etheridge song—the explicitly queer lane wasn’t a very wide one in the 90s. But the differences are largely more interesting than the similarities. In particular, note how carnal this song is in comparison to Etheridge. “Lover I burn / let me in” is one thing, but that thing is markedly different from “tell me who my mouth was made for.” It’s not Liz Phair, sure, but it’s still something more than Etheridge could do just a few years earlier.
In one sense this is just restating the premise: this is a generational change. But there’s an emerging thread over these last couple songs—one that further illuminates the frustrating toothlessness of Sobule, frankly (Tegan and Sara, it’s safe to say, did far more than kiss a girl)—a connection between sexuality and self-destructiveness that somehow renders sexuality more powerful and alluring, not less.
11. Lisa Loeb & Nine Stories, Do You Sleep (1995; Played 1997-99 Lilith Fairs)
Enough theoretical points about songs you will not listen to at the time. Let’s get back to creation myths. In September of 1995, you will turn thirteen. A few months earlier you will have gotten into They Might Be Giants, the first time that you were into an outright contemporary band instead of stuff inherited from your parents, and so, now that you are an official teenager you will embark upon one of your periodic decisions to change the sort of person that you are. Henceforth you will Listen to Pop Music. You will settle on a radio station—KC101—and begin listening. You will become a devotee of their weekly top five, which at the time they are doing as a count-up, burning their number one song at the top of the block in what is an obviously bad but oddly charming decision. And this will be the first song you fall in love with.
It is worth looking at the video, which sees Loeb looking far younger than her 27 at the time, especially when in that ridiculous but delightful sparkly dress, and which would have made your little thirteen year old heart swoon with an entirely age appropriate ardor. You will not discover Lisa Loeb’s absurdly cute glasses until your VH1 days begin a bit later, however, and by that point this song will have vanished into the ether, and the clearly inferior (though still great) “Stay (I Missed You)” will be the only song of hers you hear for years, until, armed with the iTunes store, you make this one of your first purchases, finally tracking down the song that had sat pleasantly with pleasant obsessiveness in your head for the better part of a decade when you will be pleased to learn that your adolescent taste was good. The part that stuck in your head for a decade was “you looked out the window you looked at the moon,” but on the relisten it is (and forever will be) the staccato burst of the verses, especially the gloriously obscure “do you take plight on my tongue like lead,” which, if you’re being honest, you still don’t actually know what the fuck means. This may have been your just-turned-thirteen crush of a song, but even here, there’s a depth and darkness.
12. Hole, Violet (1994; Never Played Lilith Fair)
Sorry, that was a short-lived break from theoretical points about songs you won’t listen to at the time. Let’s go back to that Etheridge/Phair/Tegan & Sara line of thought and talk about the single greatest grunge song ever written. Obviously we’re still in abjection and sexuality. “When they get what they want / they never want it again” and all. But the headline here is the explosive, propulsive rage of the chorus—the astonishing snarl with which “go, take everything, take everything I want you to” is belted out. Contextualized here she’s clearly one door down from Liz Phair. But between those houses is a faultline between “part of the Lilith Fair scene” and not. That Love was not part of the Lilith Fair is not surprising per se. Like Sinead O’Connor, you will only know Love as “a problem” at the time—you’ll be more familiar with Tori Amos’s takedown of her than with her as a person. But the reputation is clear. It’s impossible not to gesture at Nirvana here, but we’ll get one more opportunity to return to that topic. But it’s worth noting that the previous time they came up was with Garbage, another band that didn’t play Lilith Fair.
Broadly, McLachlan never really turned to rock when booking Lilith Fair. The closest she came was Tracy Bonham, a grunge-adjacent singer, but in terms of rock bands with female fronting you really only had the Cardigans (better than people remember, but only famous at the time for “Lovefool,” which wrongly positioned them as cutesy) and the Pretenders, invited as a legacy act the tour’s final year (you’ll have a soft spot for “My City Was Gone” because one of your lesbian girlfriends was from Akron). She’d go to lengths to cover her ass over the appalling whiteness of the first year’s tour, bringing in Queen Latifah and Missy Elliot to provide some brand diversity, but people who actually came up through the rock/alternativer scene? Nothing. Not even Melissa Etheridge, who would have felt profoundly obvious. It is difficult not to see substance here—to once again get the unpleasant sense that the actual Lilith Fair was constructed specifically, if unsuccessfully, to go for the comparatively sexless sexuality of Jill Sobule. In this light, it is hard to see Courtney Love’s bad girl reputation, however earned by actions it may or may not be, as a tremendous breath of fresh air.
13. Tracy Chapman, Fast Car (1988; Played 1997 Lilith Fair)
Chapman would have a small career revival off the back of “Give Me One Reason”in 1995, a track of bluesy swagger that will not do it for you until much later, but that got her the status of the only Black headliner on the first Lilith Fair. She is best known, however, for penning one of the only significant folk songs of the 1980s outside of Springsteen, to whom it is easily read as a response song. Obviously there’s a lot to unpack there. Let’s start with the paucity of 1980s folk. This is largely a historical inevitability; the genre had started in the 1960s, and so ran out of steam in the 70s before falling into the hole of the awkward interval for the bulk of the 1980s, not emerging until the 90s offered a wave of 60s revivalism.
This serves to explain how a queer Black woman was able to effectively own the genre during the era—because the white artists who would normally be boosted at her expense simply didn’t exist, and she was able to break through. Although this explanation, historically grounded as it may be, ignores the fact that the song is absolutely stunning. Still, it’s worth comparing it to the nearest thing to come out of the Lilith Fair scene, Paula Cole’s “Where Have All The Cowboys Gone,” a song that, in fairness, you’ll always have a soft spot for. But its concerns are resolutely middle class and suburban—the nice car in that one (a ‘56 Chevy) is finally sold “when we had another baby / and you took that job in Tennessee.” Not to put too fine a point on it, this implies a level of financial stability that is simply unobtainable within “Fast Car,” a song that clearly emerges out of poverty in a way that neither the 1960s nor 1990s folk scenes would. Look at the video, and standing in shadow, her facial expression holding emotions that come out of a fundamentally different reality to the Lilith Fair’s endless parade of white girls.
Are these emotions you’ll have as a teenager? Of course not. But honestly, just listen to the fucking thing. The quiet pain of the verses, with their repeated lack of surprise—you’ll be hard-pressed to find a single sentiment on this playlist with more emotional depth than “he live with the bottle, that’s the way it is.” And then that soaring chorus, becoming more doomed-feeling with every repetition as it gradually exposes its hope for a trap, revealing that starting at zero there’s still an infinity to lose. Even the guitar line, with that high G on the Em allowed to ring out in quiet yearning, is simply a wonder of song construction. Never mind who you want to be, little yet who you want to fuck. This is more important.
14. Fiona Apple, Criminal (1997; Played 1997 Lilith Fair)
You will maintain an undeserved skepticism of Apple through much of your life, due mostly to an ill-judged comment she made about Tori Amos that got seized on in the way that quotes that can be used to generate catfights are, and your failure to appreciate the brilliance of the title When the Pawn Hits the Conflicts He Thinks Like a King What He Knows Throws the Blows When He Goes to the Fight and He’ll Win the Whole Thing ‘Fore He Enters the Ring There’s No Body to Batter When Your Mind is Your Might So When You Go Solo, You Hold Your Own Hand and Remember that Depth is the Greatest of Heights and if You Know Where You Stand, Then You Know Where to Land and if You Fall it Won’t Matter, Cuz You’ll Know That You’re Right. It won’t be until Lexi praises Pass the Bolt Cutters that you finally really appreciate her. Except, of course, for “Criminal,” which is absolutely seismic. (Interestingly, it’s extremely seismic for your dad as well.)
This is another one that’s impossible to discuss without the video, which, as you’ll see, is preposterously sexy—perhaps the defining artifact of the 90s heroin chic aesthetic. But what stands out on a rewatch is the classical burlesque of Apple’s performance in it—the way in which the sexualization of her body is being wielded with meticulously fine control. The lyrics are, obviously, working with this—look at the character work in that first verse, with its ironic “it’s a sad sad world / when a girl will break a boy / just because she can,” but more to the point, look at the eye contact with the camera she establishes at “just because she can.” We’re in adjacent territory to what Liz Phair is doing with “Flower,” but this isn’t quite abjection, even as it’s clearly not quite empowerment either.
What it is, at the end of the day, is performance. Which is obvious, really. “Performance” is a pretty key concept in pop music at the end of the day. It’s tempting to say performance of gender, but much of this playlist is performing gender—Etheridge, Phair, Love, and Manson are all very much doing gender performances. So are Sobule, DiFranco, and Williams, for that matter. What makes Apple’s performance stand out is the fact that she’s playing female sexuality as villainy, in a deliciously arch way that reveals fundamental truths about the concept. Visual aesthetics aside, this is how you’re going to play things, so you’d best learn the game.
15. Brandy & Monica, The Boy is Mine (1998; Monica played 1999 Lilith Fair)
As mentioned, the Lilith Fair was a very white affair, but McLachlan was always smart enough to engage in the necessary tokenism. The final year that meant bringing R&B star Monica, who was on the downward slope of the promotion cycle for her 1998 album The Boy is Mine, which spawned three number one singles, of which this was the first. (Monica is in fact the only Lilith Fair artist to hit number one during the years the Fair was active, although Lisa Loeb and Sinead O’Connor both had prior hits, as did the Bangles, whose Susanna Hoffs played 1997.
Dueting with Monica is fellow R&B star Brandy, then starring on UPN’s sitcom Moesha; the song also appeared on her 1998 album Never Say Never, and she largely has the better time within the song—she gets the main line in the chorus, with Monica left to wind her vocal phrases around her vocal. Brandy’s slight dominance makes sense—she did co-write it, and it was originally envisioned as a solo piece before it was correctly reimagined as a duet, with the two singers dueling over the eponymous boy, a push-pull engine that lets the song glide along on the shimmer of that harp line.
You will largely miss this. You were vaguely fond of Brandy’s previous hit “Sittin’ Up In My Room” but if you’re being honest, you will miss an awful lot of Black music as a teenager, partly by not hearing it, but also by not really clicking with it when you did. This is not entirely a surprise—white suburbs in the 90s are, after all, more or less a machine for ensuring this outcome. But a perusal of the rest of this playlist will reveal the flip side of this fact: this is the only straight up pop song on it. Its vocals and songwriting are on point, but at the end of the day the thing that drives this song is its production, which you can’t really say about anything else here. The truth of the matter is that the folk tradition that Lilith Fair was largely built out of and the rock one that serves as its anxious double were largely on their way out, their grasp on the cultural zeitgeist coming to an end. The future was going to sound a lot more like this, whether or not you knew it at the time.
None of Monica’s performances at Lilith Fair ever made any of the “best of” compilations of the festival. Neither did other Black headliners like Missy Elliot, Erykah Badu, or, for that matter, Tracy Chapman, although Queen Latifah and Meshell Ndegocello both did, so it’s not a complete shut out.
16. Tori Amos, Smells Like Teen Spirit (1992; Never Played Lilith Fair)
And so we come to Tori Amos. Obviously there’s a lot of songs of hers that could be here—more than any other artist, she is seismic in your life and perceptions during adolescence, with “Precious Things” standing as an even more religious experience than “Untouchable Face.” But in the closing stages of recording for her debut Little Earthquakes she cut a triptych of covers to use as b-sides for the “Crucify” single. Two of these showed off her classic rock bona fides—the Rolling Stones’ “Angie” and Led Zepplin’s “Thank You.” For the third, however, she turned to what was at the time only an eight month old song, taking the bull by the horns and doing Nirvana’s “Smells Like Teen Spirit” at what was essentially the height of its popularity.
The original matters here. This was the song that started grunge and recentered alternative rock away from the UK and on the west coast of the United States—ironically a far more foreign location to you. You will have problems with this. You’ll never own a Nirvana album growing up, and while you’ll eventually come to appreciate “Smells Like Teen Spirit” on the level of a thing that sometimes comes on VH1 and isn’t that annoying, the fact of the matter is that you’ll know the Weird Al parody far better than the original. There’s no big secret here; masculinity is simply uncomfortable, and this is an extremely male song, full of dick out swagger.
Tori Amos’s version, however, is something altogether different. The swagger is replaced with a quiet menace—listen to the way the song turns faintly upon “a dirty word,” and the way in which she uses dissonance throughout. Where the original was belted out, screamed to the point of incoherence, this is soft, almost whispered straight into your ear, the intimacy making its threatening aura all the more unsettling. We’re in territory we haven’t really seen since “Jackie”—a femininity of monstrosity, uncovered within the apex of 90s pop masculinity.
Obviously this is extremely trans. Which is ironic, given the popular theory (advanced adamantly, it must be admitted, by Lexi) that Kurt Cobain was trans. But the biographical interpretation, while tremendously interesting, is ultimately beside the point. You will have no idea, during the 90s, that the song’s original singer was plausibly a closeted trans woman. You don’t have to. You have this song, which is already profoundly trans. In a decade of desires so unspeakable they cannot be fully conceived of, here at last is the act of transformation, thrumming with sacred terror.
17. Indigo Girls, Fugitive (1994; Played 1997-99 Lilith Fairs)
The Indigo Girls are one of those duos—like They Might Be Giants—in which both members are individually songwriters and lead vocalists. Also like They Might Be Giants, they have one that writes all the popular songs. For the Indigo Girls, this is Emily Saliers. Here, we’re almost done, so let’s do a playlist within a playlist. Start with “Closer to Fine,” off their self-titled major label debut. It’s the one everyone learns on guitar, and is the other significant 80s folk song. A cool then-lesbian who later came out as nonbinary will play it at CTY and change the line about “got my paper and I was free” to “got my paper, set me free,” delivering it with theatrical pleading, and it will burn itself into your mind. Then go to “Galileo” and “Ghost” off of Rites of Passage, their best album, a one-two punch of pure folk pop perfection and an all-timer of a ballad. Finally, off of the same album as this, do “Least Complicated,” which was the single. (Indeed, note that three of those four have music videos)
These are mostly the songs you will love as a teenager, because they are very, very good. Saliers has well-honed pop instincts, in many ways the best version of the Dar Williams/Jill Sobule/Jewel paradigm, an earnestness that’s generally played adroitly enough to avoid bathos. (See “I bought you that ring / cause I never was cool” in “Least Complicated”)
This, meanwhile, is an Amy Ray song. Let’s do an equivalent playlist. Do “Blood and Fire” off the self-titled, “Hand Me Downs” off Nomads Indians Saints, and “Jonas and Ezekiel” off of Rites of Passage. Ray is, first and foremost, the butch of the group, writing rockier songs with the same smoldering disaster lesbian energy as Melissa Etheridge (“Blood and Fire,” in particular, sounds like the template for all of Melissa Etheridge’s good songs) but, crucially, never getting to be the lead single. She will definitively be your less favored Indigo Girl, at least in adolescence, though you’ll later reevaluate this.
“Fugitive” will be a big part of that. Like most of Amy Ray’s best songs, it’s long on barely checked libidinous desire—”I’m harboring a fugitive, a defector of a kind / And she lives in my soul and drinks of my wine” is a hell of a start. But it crescendos into something new. There’s a fleeting sense of prurient interest akin to some of Etheridge’s anxieties—”are they coming for us? Cameras or guns? / We don’t know which but we gotta run / And you say, ‘This is not what I bargained for’” is at least adjacent to Etheridge’s constant fear of shame and exposure. But it eventually spirals into something far more abstract, its concerns becoming something much more rooted in self-actualization. At the risk of stating the obvious, you could pretty trivially make a trans reading of this in which the fugitive is the female self. It’s clearly not quite what’s going on, at least if the paratext is taken into account at all, but it’s not entirely off either.
Which is the ultimate takeaway here. This narrow band of music—female singer-songwriter stuff of the 1990s—can seem stifling in many ways. Its horizons are brutally apparent time and time again. And sure, in many ways it was. That’s how subgenres work. But the flipside of this, just as important, is that there are accomplishments that can only be made by going deep into a style. Something like “Fugitive” was never going to arise except as the end of a long chain of influences, from someone whose work wasn’t rooted primarily in populist acceptance but in working the margins of form and genre. This music and era has its facets of cringe, yes, but what doesn’t? 90s alternative has “Everybody Hurts” and “Bullet With Butterfly Wings.” But for all that this looks painfully dated, the fact remains that there’s an infinite depth here, and what you’ll lose yourself in was always more than just the solipsism of your own dysphoria.
18. Suzanne Vega, As Girls Go (1992; Played 1997 Lilith Fair)
The other thing to note about the Indigo Girls is that they were both out lesbians. This will certainly be part of the appeal at the time—one of the only ways you can approach the thing that you want, through the oblique angle of cultural consumption. This also meant that the Indigo Girls repeatedly played the Michigan Womyn’s Music Festival, an all-women music festival founded in 1976 which, starting in 1991, operated with what was called the “womyn-born-womyn” policy, which is to say a complete ban on trans women’s attendance. (As did Ani DiFranco and Jill Sobule; historical setlists for MichFest are hard to find, but one doubts they were the only overlap.)
This policy led to significant outcry within queer and feminist spaces, and eventually saw the festival’s demise in 2015. The Indigo Girls played the festival repeatedly during this time, and in 2005 Amy Ray gave festival coordinator Lisa Vogel a platform to justify the policy. Eventually, in 2013, the band changed tracks, declaring that they would play the festival one last time, donate the money to trans causes, and make a statement from the stage protesting trans exclusion, although even there they stressed that “The current intention for the Festival to be for “Womyn born Womyn” only grew out of an important necessity to honor the idea that womyn have a variety of self expression and appearance and they need a safe space where their womynhood is not in question as they stand in many different places on the spectrum from femininity to masculinity. This intention has a very important historic basis and has kept the space safe for many womyn over the years.” These days, for what it’s worth, Amy Ray describes herself as genderqueer and as having dysphoria, though she stresses that she does not consider herself trans and uses she/her pronouns.
Which brings us to this song; the cold slap in the face in which you are reminded that if this was for you, it was only ever by accident. This is made all the more painful by the fact that Suzanne Vega is legitimately great; it’s only by dint of the best songs being less folk oriented that Solitude Standing doesn’t have a song that expands the Chapman/Saliers hegemony over folk relevance in the 1980s, and even still it has “Tom’s Diner,” (but see also this version) which, on purely objective historical terms, is blatantly the most important song of the decade. Her 1992 album 99.9F°, which embraced electronic sounds and industrial influences, is an all-timer. And then there’s this song.
Redemptive readings certainly abound. There’s that “doesn’t matter to me / which side of the line / you happen to be / at any given time” closer that clearly gestures at some level of trans acceptance. Much like “I Kissed a Girl,” there’s something potentially fruitful in the way in which gender becomes a site of play. And there’s perfectly good evidence that, like most people, her opinions evolved over time and she’s better on trans issues now.
But all of these defenses simply falter in the face of the sheer nastiness of the song. For fuck’s sake, the third line is “still kind of look like a guy.” Then you get “Damsel in distress / not exactly natural / stunning none the less,” in all its dripping condescension, the lurid questioning “did you ever keep the date / with the steel side of the knife,” made worse by rhyming it with “dark side of the life.” Or just the sing-song, mocking outro of “as girls go,” a title line that exists purely to undercut the one crumb of validation the song offers. This is an absolutely horrible song with nothing to communicate but its own transphobia.
This is what they think of us. Never forget that. No matter how much you fall in love with popular culture, it’s never going to love you back.
19. The Nields, I Know What Kind of Love This Is (1996; Played 1998 Lilith Fair)
As mentioned, you’ll dive deep on this subgenre, especially its folkish elements. You’ll follow Dar Williams to Cry Cry Cry, her folk supergroup with Richard Shindell and Lucy Kaplansky, a covers band that did a version of this, leading you to The Nields, a minor folk band consisting of sisters Nerissa and Katryna Nields and a couple other members. They did a couple of decent songs including the genuinely hilarious “I Hate MCI.” And, of course, this.
It’s a deceptively simple song, driven in the end by little more than its vocal, sung in a simple harmony. What stands out, however, is the sense of creeping awfulness. Its first verse is subtle, its worst and ugliest emotion coming in the lyrical turn of “I was there when we made it,” and the subsequent lyrics that make it clear that this is the “ill-advised hookup” variety. Nothing save for “wallflower shade” gestures at age or setting. All we have, at first, is mood.
It’s in the second verse, with its flood of details, where things take a turn to the deeply unsettling. “Pretending I am dead” probably isn’t the outright necrophilia reference your teenage mind will go for, but it hardly matters. “In my parents’ bed” and “you can pretend that you are blind” combine with it for something unsettling in its abjection, utterly devoid of any eroticism. And then, of course, the final verse, where the context becomes unavoidable, where it becomes clear how futile the sex was—that wallflower shade has simply been traded for a new flavor of rejection. It’s heartbreaking.
It’s also, you will come to suspect, very close to what would have happened if you’d gotten to be a girl for this era. You’d have been the shy wallflower who threw yourself at whatever would take you. Even as an egg, you just substituted pretending you’re dead in your parents bed with a blowjob from your debate partner on a shitty sofa where you were watching Lost Highway, another guy seated on the other side of her, and to be honest you can’t even remember either of their names. You didn’t even do that for some ill-conceived play at social capital. You just did it for the illusion of being desirable. This is what the story of you as a girl would have been: shame and objectification.
And yet listening to it, what will be most agonizingly clear is that you still want it. More than you want to look like Shirley Manson or Lisa Loeb, more than you want your swearing to hit like Ani DiFranco or Liz Phair, than you want your voice to shine with the menace of Tori Amos or Sinead O’Connor, what you want is simply to have had this shitty adolescence instead of the one you got. Andrea Long Chu writes “a fantasy doesn’t have to be a lie. It’s just something you’d believe even if it were a lie.” But perhaps another way to put this is that a fantasy is something you’d still want even if you knew it was going to be terrible. Being a teenage girl isn’t better than being a teenage egg. It’s just the way you’d have rather been hurt. You know what kind of love this is.
1. “Who Will Save Your Soul,”“Where Have All The Cowboys Gone,”“Sunny Came Home,”“One of Us,”“Stones in the Road,”“Everyday is a Winding Road,” and “Carnival” would be my picks from those artists, although there’s quite a range of quality across those seven.