So I’ve been listening to this playlist a lot lately. Its title in my phone is Lilith Farewell, because I’m an inveterate punster, but it doesn’t consist exclusively of women who appeared at Lilith Fairs. That’s the general idea, though — mid-late 90s lady singer/songwriters with a folkish-rockish bent, the more thoughtful and plaintive the better. And (the important thing) the songs were to one degree or another radio hits. I heard them all at the time, though I haven’t listened closely to any of them in a decade, and some I never did. But because I’ve been listening to them a lot recently, of course I’ve thought of one or two things to say about them.

The seed of this playlist was planted a couple of years ago, when a writer I enormously respect made the offhand comment that her tastes in popular music — Sarah McLachlan and the like — were undesirable, especially what with all of these music critic people around on Tumblr. I responded with the usual line — nothing good or bad but thinking makes it so, not my cup of tea but no reason it shouldn’t be yours — but it got me to thinking. Why isn’t Sarah McLachlan my cup of tea? Why should I be able to casually dismiss her, when I don’t extend the same privilege towards the Black-Eyed Peas or Céline Dion or whatever other critical punching bag you care to name? I’m familiar with the usual arguments — Manny Farber’s white elephant art, Gilbert Seldes’s faux bon, the casual internet usage in which “white people” is a term of derision — but they don’t settle anything for me.

Over the years I’ve come to be deeply suspicious of any knee-jerk dismissal of women in music. This is largely because I grew up jerking that very knee; the adjective “Lilith Fair” has until quite recently been a pejorative in my dialect, and through circa 2006 I tried hard to believe that the only way a woman could be interesting in music was if she imitated a man. That I think differently now is hardly to my credit — I more or less had to be browbeaten into understanding that music made by and for women is just as truthful, revelatory, and necessary as music made by men, which (save for specific subgenres like metal) always assumes a general audience.

But this music assumed a general audience too, and, for a while anyway, found it. Looking up artist discographies on Wikipedia, I’m struck by some of the sales figures recorded there — Sarah McLachlan’s Surfacing sold eight million copies in the US (by comparison, an inescapable juggernaut like Adele’s 21 has sold four million), and it wasn’t even one of the biggest records of 1997. “Records now sell less than they did in the late 90s” isn’t exactly news, of course, and I don’t want to refine too much upon the disparity. It’s just worth remembering that there was a period in the recent past (well, recent-ish: any Millennials reading may consider this a glimpse of antiquity) when serious women singing serious songs about serious subjects were not just awarded devoted cults and critical respect (we have our St. Vincents and EMAs, our Cat Powers, Neko Cases, Joanna Newsoms and Laura Marlings today), but mass acceptance and sales bonanzas. Don’t get me wrong, I love unserious women singing unserious songs about unserious subjects too (Ke$ha 4 lyfe), but the closest we come to these women today is in singers Cobie Caillat and Christina Perri — pleasant enough, but fundamentally unserious in a way that the late 90s didn’t encourage its young white guitar- and piano-playing women to be.

There are plenty of arguments to be had about whether this is a good or bad thing, about whether the the seriousness and identification with feminism of these late-90s artists did more to erase non-white, non-middle class women than it did to give women a voice in popular music that they hadn’t had on such a scale before, and whether some of the late-90s names visibly missing from this playlist — Lauryn Hill, Liz Phair, Sheryl Crow, Erykah Badu, Shakira — ultimately ended up being more important. I take it for granted that they did; but deciding who feminism belongs to is very far from being my call. All I can report on is my personal response.

And what I hear is a lot of complexity and thoughtfulness; if I hear that thoughtfulness as centering around issues raised by feminism (femininity and masculinity, domesticity, self-determination, the limits of allowable expression), that may owe more to my own desire to hear it than to anything intended by these women. There’s certainly more musical variation here than I initially expected when I lined all these songs up in my head before downloading them and listening to them. From Shawn Colvin’s studied Americana to Fiona Apple’s damaged LA art-pop to the programmed beats underlying three of the songs, they undercut my folk-pop expectations at every turn. As a whole, though, I think they form a sort of fractured whole, a mosaic in which each piece complements all the others. Every good playlist should, of course; but few of my playlists cohere as well as this one.

1. Sarah McLachlan “Building a Mystery”

I remember first stating that I couldn’t stand Sarah McLachlan in the spring of 1996, on the road to school between Antigua Guatemala and Ciudad Guatemala. I can’t remember why I said so at this distance — I expect it was a combination of wanting to needle the girl we carpooled with, who loved her, and being bored by what I perceived as formless, droning songs expressing sentimental clichés in that fluting, too-pure voice. (When I was younger, I thought rough voices were better than clear ones. Not sure why; sexism, probably.) I suppose I’d only heard “I Will Remember You” at the time, and I disliked it the way I disliked Michael W. Smith’s “Friends” and Michael Jackson’s “Earth Song” and Mariah Carey & Boyz II Men’s “One Sweet Day” — songs that formalized particular sentiments, that forced themselves upon particular events, flattening, normalizing, and commodifying nostalgia, friendship, sentiment about nature, and grief. Later, “Angel” served similar purposes on a somewhat larger scale (it might be the single most-used song in TV dramas 1998-2005), but when I looked up Sarah McLachlan on Wikipedia to figure out what song I remembered her for, “Building a Mystery” jumped out as the only obvious choice. 

She’s quoted as saying it’s a song about how we all hide insecurities and cultivate façades, and the lyrics, once I got around to reading them, suggest a portrait of a particular kind of 90s boho dude (in rasta wear and suicide poems, a beautiful fucked-up man), but when I first listened to the song in the context of this playlist I zeroed in on all the religious references and the barely-buried Celticisms in McLachlan’s voice and melodies and heard a celebration of pagan womynhood. (This isn’t the last time I’ll hear more progressive or radical things in these songs than may have been put there; but surely many of their listeners hear them as more conventional and innocuous than they really are, so it evens out.) The full-band crunch around her gives the song some heft, organ and electric guitar tying it to the hippie originalism (there’s even an old-fashioned backwards-guitar solo in the bridge) that the song could be a critique of, if McLachlan was ever so impolite (or unsubtle) as to make overt critiques. The title phrase, “building a mystery” could be a criticism of manufactured personas — but (her beautiful, blank performance offers no hints) it could equally be an ode to self-determination. The internet age has only made more obvious the fact that being one’s self requires a certain amount of performance, of mythology-building. We are all fundamentally mysterious to each other; the explanations we offer have to be chosen so carefully.

2. Fiona Apple “Criminal”

Of all the singers on this list, Fiona Apple might have the best critical reputation today, at least among a certain indie-identified contingent, thanks to her collaborations with Jon Brion and Van Dyke Parks (both of whose work can be heard here) and her jazz-inflected singing. (I hear a lot of Nina Simone on her debut album, and Apple’s relatively low-pitched vocals can resemble Cat Power’s or, on occasion, Neko Case’s.) “Criminal” was a pop hit, and her Kate Moss frame and big-eyed beauty were interpreted through the remorseless atomizing framework of late 90s pop, possibly the most efficient money-making machine in entertainment history. Her subsequent retreat from that machine, in the form of the unwieldy When the Pawn… and the label-delayed Extraordinary Machine, is often framed as an indie-pop hero’s journey, though reality is more complex, and Apple still has more in common with smart industry players like Aimee Mann or even Mandy Moore than with, say, St. Vincent.

Still, “Criminal” is the most unconventionally-produced song on this playlist, with its rumbling piano, flute bursts, orchestral shudders and thick lead bass lines. Its opening line — “I’ve been a bad, bad girl” — could be right out of contemporary teenpop, and you could say that the entire careers of Britney Spears or Christina Aguilera were deconstructions of that one sentiment. But the next line — “I’ve been careless with a delicate man” — is cagier, and I can’t help hearing it as at least somewhat sarcastic. Not that there aren’t delicate men who are emotionally damaged by women (it’s the basic premise of half the R&B ballads ever written), but Apple’s cool deadpan suggests that she’s flinging a guy’s accusation back at him, not feeling real anguish over having hurt him. He’s the one guilt-tripping her into feeling like a criminal, and she’s looking for a good defense, not a way to make it right — because she’s just as much a victim, if not more. Again the language of religion (“I need to be redeemed to the one I’ve sinned against”) is used as metaphor — the entire song can be read as the speech of a penitent in a confessional, but it’s hard to believe her penitence; she relishes the sound of the words in her throat too much for that. It’s an arch psychodrama, and the giddy, whirling production matches the headfuck. 

3. Paula Cole “Where Have All the Cowboys Gone?”

Apparently this song comes with some baggage. I can’t say I fully understand the point of view of those people who think it’s one of the worst songs of all time, but its reign of inescapability was apparently during one of those brief periods in the 90s when I wasn’t listening regularly to the radio. More generally, I have little invested in policing the boundaries of taste, especially from so long ago. (Those lists of Worst Songs Ever that circulate are as uninteresting to me as similar lists of Best Songs Ever — give me an aesthetic over a consensus any day.) I guess I can hear how the doo-doot, da-doo-doot backing vocals would be irritating, and  I suppose people who can’t think about rural or small-town America in any but the most condescending, caricatured terms would be rubbed the wrong way by its use of longstanding tropes about domesticity, masculinity, and gender roles. But my earliest memories are of farmers and ranchers, and I’ve known plenty of women who believed in and longed for the rugged romance-novel vision of life that Cole complicates and ironizes here.

If anyone doesn’t hear that complication, they can’t be listening very well. The final line of each verse, in which she assigns the gendered division of labor (“I will do the laundry/You pay all the bills”), should be enough of a tip-off that this is no idealized fantasy, but just in case any traditionalists are thinking of claiming the song as their anthem, the final version of the line (“I will wash the dishes/While you go have a beer”) is delivered with such bitter contempt that it’s impossible to hear as an endorsement of the arrangement. It may not be a Friedanesque screed (not a bad thing; screeds generally don’t make good pop songs), but it smuggles enough domestic discontent into the romanticist architecture of the song that the final minute, in which Cole interpolates both cowboy whoops (yippie-yah, yippie-yay) and less structured warbles that might or might not be a reference to Native American chants, comes as a sort of healing relief from the grind. There are all kinds of subtle touches to the production, from the midtempo rhythm that suggests the clip-clop of traditional movie Western themes to the rustling noises in the hushed spoken-word sections, that I wonder less why the song is so hated in some quarters than how it ever became a hit in the first place. Cole’s voice moving into its shivery falsetto is only a partial explanation. It even took me until just yesterday to realize that “I Don’t Want to Wait” was by the same person — I’d been thinking of it as a light R&B song in the Des’ree mold for decades.

4. Shawn Colvin “Sunny Came Home”

I must have heard this song hundreds of times in 1997 and 1998, and I can’t believe it took me until this week to realize it was about… well, what it’s about. At the time I heard it as just another song on the radio, barely different from the Wallflowers, Goo Goo Dolls, Sister Hazel, and Edwin McCain songs that surrounded it. A couple years later, when I started downloading every song I could remember ever hearing on Napster, I couldn’t remember which one was Shawn Colvin and which one was Shawn Mullins. I was hardly alone; I’m pretty sure I downloaded a copy of “Sunny Came Home” that was tagged as being by Jewel. (Because all female singer-songwriters in the late 90s were indistinguishable from one another. Which was kind of the original premise of this playlist, so I’m not sure why I’m being so sarcastic about it.)

This song won the Grammy’s Record of the Year in 1998, a piece of trivia which I would have filed away a week ago as further confirmation of the Grammy not being an award at all (pace Simpsons). But now I’m just impressed by the trick Colvin pulled; smuggling a story about a woman who sets fire to her home in order to free herself from an intolerable life into a soothing, mandolin-driven song with a catchy chorus which could be read as life being kind of okay. I’m pretty sure I sang along with “days go by, I’m hypnotized” many times in the car, and in retrospect it’s an excellent description of the late 90s in general; unsustainable prosperity, a secretly crumbling global infrastructure, and sheer mule-headed complacency leading up to a decade of terror, collapse, and violence which the apocalyptic visions of the late 90s seemed to eerily predict. “Sunny Came Home” is about personal rather than societal apocalypse, and so very much in the vein of songs like “The Ballad of Lucy Jordan,” but if records like “Sympathy for the Devil” are allowed to stand in for the way the utopian dreams of the 60s turned nightmarish in the 70s, I move we push “Sunny Came Home” as the turn-of-the-century version.

5. Meredith Brooks “Bitch”

It was probably a year or two after this song’s chart heyday that I first found myself singing along to it and suddenly stopped short, confused. I hadn’t known I knew it. In fact I didn’t even know what it was. Who sang it? What was it called? This is, I gather, a relatively normal state of affairs for casual pop listeners, but I do very little casually; practically the first thing I did when I first discovered the glorious information repository of the Internet was to look up the titles and performers of songs I’d taped off the radio a couple years back. (The Shazam app is my lifeblood today.) I was still callow enough that the song struck me as slightly unsettling — a bitch, after all, was a terribly bad thing to call someone, or to be, though the “goddess on my knees” line scandalized my devout ears even more — which is why it’s faintly ironic that it is, of the nine songs on this list, the weakest of sauces.

A certain kind of music fan is always conflicted about one-hit wonders (which, for the purposes of this… thing I’m writing, Meredith Brooks is; I know that “What Would Happen” went to #46), because they fall between two stools. Awarded neither the commercial validation of a long-term pop career nor the gritty authenticity of an under-the-radar career where only true fans can know and love them, one-hit wonders make clear the injustice of pop’s unequal distribution of resources, as well as the basic unfairness of the indie-oriented critical worldview. Never try for pop success, and you’re a darling; try and succeed, and you’re a fact to be reckoned with; but try and fail, or succeed only briefly, then fail, and you’re a cautionary tale, a punchline, a whipping bag. When 30 Rock showed Liz Lemon strutting along confidently to “Bitch,” the joke was the song choice just as much as Tina Fey’s ridiculously nerdy moves. It’s a marker of how pop-obsessed I am that I initially read it as reclamation rather than a mockery — and I do think it’s a worthy reclamation project. The millions of middle-aged women who have it on their jogging mix are way ahead of me, of course, and I wouldn’t be doing my job as a caviling mansplainer if I didn’t point out that the second verse and the “you wouldn’t want me any other way” refrain feed directly into Woman-Changeable-As-The-Tides stereotypes. But the simple embrace of the title word (only a year after the founding of bitch magazine) is plenty of empowerment for any #2 hit. The rubbery beat and crunchy guitars (sounding a bit like leftover Madchester, oddly enough) may have made it commercial, but Brooks’ performance, which borrows Alanis’ Morissette’s way of attacking a lyric while leaving her more idiosyncratic stylistic choices behind, makes it resonate. I still find myself singing along.

6. Alana Davis “32 Flavors”

If you’d asked me a week ago if Ani DiFranco had ever had a single in the Top Forty, I would have laughed and told you not to ask silly questions. That was before I learned that “32 Flavors” was written by Ani DiFranco; but then, I wouldn’t have thought that I knew a song called “32 Flavors” before an Allmusic Similar Artists-inspired downloading binge brought it back into my life. Unlike most songs of the era, I have no actual memories of hearing it, save for ruminating once or twice on the Baskin-Robbins reference — but I knew it intimately once I heard it again: the hushed, jazzy phrasing that then reminded me of Des’ree and now makes me think of Norah Jones (who has never had a song this good to sing), and the swirling, liquid guitar loop that then reminded me of Duran Duran’s “Come Undone” and now makes me think of acid jazz, especially married to that gorgeously dusty trip-hop beat.

On the vast archive of pop-music scholarship and collegial discourse that is Songmeanings.net, username swandive notes, “This song in [sic] ORIGINALLY WRITTEN AND RECORDED by Ani Difranco [sic] 2 years before Alana Davis slaughtered it with her icky hiphoppy beat and slight lyric changes.” Icky hiphoppy beats aside (and it’s worth noting that while Alana Davis is the only woman of color on this list, the beat’s not any funkier than those on either side; a shuffling breakbeat was one of the standard tools of pop in the mid-to-late 90s), the appeal to originalism is worth spending some time on. DiFranco’s original, which has an extra verse and no chorus (the rushing “I am what I am” hook that punctuates Davis’s version was apparently her own invention; well, hers and E. C. Segar’s), is lovely (and just as rhythmic), at least while DiFranco is singing. It descends into faintly embarrassing cod-African chanting and drumming after a while, which might make a thematic point (Ani DiFranco is large, Ani DiFranco contains multitudes) but knocks her elegant song structure all to hell. I’ll take Davis’s slaughtered version, thanks; by interpolating the chorus and cutting out the most personal of DiFranco’s verses, she universalizes the song, dragging it out of the solipsism of biography and into the community of pop, where (like “Bitch”) it can provide a statement of self for as many women, or non-women, as care to embrace it.

7. Natalie Imbruglia “Torn”

As I mentioned, the original impetus for this playlist came from a post several years ago by Michelle. Probably the most recent impetus for it, though, was the climactic scene of a recent episode of Happy Endings, in which Megan Mullally and Casey Wilson, playing mother and daughter, sing “Torn” as a duet at a boat show. It’s hardly an original climax — funny people singing unlikely songs has been a show-closing staple in comedy since vaudeville, if not earlier — but as with 30 Rock’s use of “Bitch,” it reorganized the song’s importance in my mental catalog of pop. Once upon a time I’d liked this song, or at least I listened to it fairly frequently (not that I could get away from it at the time), and since Imbruglia was filed alongside McLachlan, Apple, Cole, and a handful of others in my mental index, the entire … uh, file folder, I guess? this metaphor is out of hand … shifted up towards the surface. Then of course I started to look them all up on Wikipedia and discovered that Imbruglia was a *sniff* pop singer, a proto-TashBed who only sang to jangly guitars because they were in at the time, a former soap actress and Australian to boot, so her inability to pronounce the R in torn wasn’t due to a charming Long Island accent, but a boring old Commonwealth one.

As if the rest of this list isn’t all pop songs sung by beautiful women. And “Torn” in fact has decent indie-rock bona fides; it was written by L.A. grungewagon band Ednaswap, whose slogging, fuzzed-out original sounds uncommonly like a demo for Imbruglia’s bright, glittering, and more plaintive cover. I remember marveling at the time that there was a song about a woman “bound and broken on the floor” on regular, non-metal radio; even today, without reference to the video or the promotional imagery, the song can overwhelm with its described — and, thanks to Imbruglia’s vocal limitations, audible — vulnerability. A possible reading of the song is that it’s too vulnerable, too beholden to traditional female stereotypes of emotional fragility, codependence, and Needing a Man: all the usual anti-pop arguments trotted out by people who sometimes even call themselves feminists. But placed here, at this point in the mosaic, I hear it as simply another of DiFranco’s (or Davis’s) flavors, of Brooks’s multiple singularities. Sometimes we are devastated, and we need pop songs that express that too.

8. Jewel “Foolish Games”

Of the nine women on this list, Jewel is probably the easiest punchline; her single name, her books of poetry, and her dedication to absolute somberness (at least in the radio hits which were most people’s, including mine, only exposure to her) made it easy to dismiss her as a pretentious charlatan. As did, to be completely honest, her gender: pretty girls aren’t supposed to take themselves quite so seriously, in the eternal estimation of dudes who take themselves exceedingly seriously indeed. But for the brief period when Jewel was the most beloved and imitated singer/songwriter in America, she was unstoppable. “Who Will Save Your Soul” was a bigger hit and “You Were Meant for Me” had more general utility, but “Foolish Games” was the one that resonated the most strongly with me, if only because I’d heard it more recently than any of the others. (2003? 2004? Whenever the last church retreat in which I participated in a particular skit was.) There was a girl I knew then who more or less wanted to be Jewel; I think I saw her at the coffeeshop today, but we didn’t make eye contact. (Yes, seriously. I am thirty-three.)

It’s surely one of the slowest-tempoed songs to be such a big hit, at least in the last twenty years; a fact made up for by the chord progressions from “Diamonds and Rust” (a very apt reference point, as it turns out) and by Jewel’s expressive singing. There’s a reason the song worked so well in church skits: her understated voice, moving from lip-quivering grief to outraged sneer in the space of a line, is a great theatrical instrument, and “Well excuse me/Cause I’ve mistaken you for somebody else/Somebody who gave a damn/Somebody more like myself” is as fine a piece of pop writing as I’ve ever heard. Like Imbruglia in “Torn,” she’s devastated by the disillusionment of a relationship that wasn’t what she thought it was; unlike Imbruglia, she fights back. “You loved Mozart,” she purrs sweetly, ego-flatteringly, just before indicating her boredom with his tedious mansplanations while she was just trying to work on her craft. Not that it doesn’t still hurt — she’s not Fiona Apple in “Criminal,” she’s really broken up — but she has the confidence of her own voice and the magisterial sweep of the song to back her up. The final portrait she paints is that of a posturing, judgmental bore, a Lloyd Dobler who didn’t win the girl over, because she wasn’t just a fantasy figure but a person, with her own ideals to live up to and her own judgments to make. No punchline voids that.

9. Natalie Merchant “Kind and Generous”

I used to mix up the Natalies frequently back when they were both on the radio regularly. Once I learned about one of their connection to 10,000 Maniacs, I had a bit more context, but it still took me a while to remember which one was Imbruglia and which one was Merchant; it didn’t help that before this week I hadn’t listened to a Natalie Merchant song (save for her appearances on the Mermaid Avenue sessions) in ten years. I was originally going to playlist “Jealousy,” because that was the only song whose melody came to mind when I read its title, but after spinning quickly through her discography I remembered how much I had loved “Kind and Generous” when it was on the radio. Regretfully, I left “Jealousy” — and “Wonder” — and “Carnival” — (good grief, did she have a single I wasn’t familiar with?) behind; “Kind and Generous,” after all, was the perfect capper, itself kind and generous, playful and healing, to this playlist of troublesome emotions and subtle if sometimes obvious textures.

In Christian circles, there are (or were; I’ve been out of it for awhile) frequent rumors flying that this or that popular song is secretly about God, and “Kind and Generous” was eagerly snapped up by the faithful; I knew churches where it was sung like any hymn, attended weddings where it was the father-daughter dance, and I’m pretty sure I once or twice sang along with it in the car and called it a prayer. Today a song of this sort would be unambiguously “with love to all my fans,” but Merchant’s indie-bred reticence and very 90s earnestness (Tigerlily can feel downright didactic at times) keeps it ambiguous, universal, and all the more useful for it. If you choose to read it that way, it circles back around to the religious symbolism in “Building a Mystery” — but either way, there are not and never have been enough na na nas in pop.

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N.B. I considered several songs for this playlist which ultimately didn’t make it, but are worth pointing out as being in the same general wheelhouse: Abra Moore’s “Four Leaf Clover,” Tracy Chapman’s “Give Me One Reason,” Billie Myers’s “Kiss the Rain,” Heather Nova’s “London Rain,” Tracy Bonham’s “Mother Mother,” Joan Osborne’s “One of Us,” Dionne Farris’s “I Know,” Tori Amos’s “Spark,” Jennifer Paige’s “Crush,” and Alanis Morisette’s “Uninvited” (among many other Alanis Morissette songs). Plus now I’m listening to albums by Dar Williams, Jonatha Brooke, and Ani DiFranco, and creating a related playlist of songs from the late 80s and early 90s featuring the Indigo Girls, Suzanne Vega, Michelle Shocked, Melissa Etheridge, k.d. lang, Edie Brickell, and, again, Tracy Chapman. I don’t visit eras so much as fall down rabbit holes. But this is quite long enough as it is.