One of the interesting things about working with college students is seeing what music that I think of as from “my time”—let’s say the ‘90s and ‘00s—is alive for them: The Mountain Goats, very intensely. The prematurely deceased are always fascinating: Nirvana, sure, but especially Elliott Smith. Built To Spill. Recently, for some reason, Grandaddy (my working theory is that the combination of bedroom singer-songwriter with cheapish synth patches exactly matches the kind of music it’s easiest for them to make in their dorm rooms).

Often, this comes up when they bring a song they want to talk about into class. A few years ago, there was a run on the Roches’ “Hammond Song” (a TikTok thing, apparently? Whenever I’m not sure, it’s a safe bet), and Liz Phair: 2023 was the thirtieth anniversary of Exile In Guyville, with, of course, an associated tour, reissue, and round of publicity. All the students were interested in “Divorce Song”; everyone knew it and loved it.

At the beginning of each semester, I ask my new songwriting class for a list of their dream guests—I am, loosely speaking, in the music business, often I know someone who knows someone, and usually people are open to talking craft with young writers. When one young woman named Ani DiFranco, I was intrigued—that was, as the quote goes, a name I hadn’t heard in a long time. Actually, that wasn’t even true: I knew people in the Righteous Babe orbit, and I’d worked on at least one record the label put out. And it was a name that was important to me.

I had been, as a teenager in the mid-90s, a very intense DiFranco fan (though no fan would call her anything but by her first name). I was, without being able to articulate it exactly, on the hunt for songwriters who treated an acoustic guitar as an orchestra and a rhythm section in itself, with the melodramatic intensity of the bands I responded to viscerally but whose lyrics too often felt like afterthoughts. (Another acknowledged DiFranco influence is Joan Armatrading, who once said, “The reason I think my acoustic style developed in the way that it did was because when I write, I tend to hear lots of things—the bass part, the keyboard bit, some strings, what kind of percussive sound it should be. I’m trying to play all those things at once, so my style is quite aggressive.”) DiFranco gave Joni Mitchell’s open-tuning explorations a folk-punk force—check out the virtuosic riff to 1995’s “Cradle And All”:

In large part, I taught myself guitar (and a hefty dose of ear training) by transcribing the songs of Mark Eitzel and Ani DiFranco. I particularly loved playing the sweet, understated song-about-songwriting “This Bouquet”:

…a fascination which later morphed and resurfaced in the Hold Steady B-side “Two-Handed Handshake”.

And she was an icon of DIY—she’d turned down the million-dollar label offers to self-release her six-figure-selling records (and, not for nothing, those of other like-minded iconoclasts). Her 1994–98 rise and peak was a phenomenon; her fans combative, earnest, obsessive, with an unhealthy sense of entitlement about her personal life; her playful delight in tweaking their expectations was part of her giddy appeal:

People talk about my image
Like I come in two dimensions
Like lipstick is a sign of my declining mind
Like what I happen to be wearing
The day that someone takes a picture
Is my new statement for all of womankind…
Quick, someone call the girl police and file a report

(It reminds me a little of Against Me!, a later cult phenomenon with an adversarial relationship with their graspingly possessive fans.)

I’m probably not saying anything anyone reading this doesn’t know, or remember.

Obviously there’s no formula for why one artist is taken up by younger listeners versus another. But I was struck by the disparity between the number of young people in the class who knew, for example, Phair (all of them, enthusiastically) and the number who knew DiFranco (just the woman who’d requested her); and I think it illuminates something about the power a certain kind of music industry power and cultural capital still retains in a time in which omnivorous taste is reified and the idea of the “guilty pleasure” is often treated as passe.

You know the deal: the splintering of the mainstream/alternative binary; the remapping of Bourdieuvian taste profiles from elite/upper class, aspirational/middle class, functional/working class to big-eared “I listen to everything” snobbery; shuffle-playlist listening+poptimism=”let people like what they like,” and so on. If I ask students to identify a guilty pleasure, the best we can come up with (besides, maybe, musical theater—more on that later) is the idea that one might not admit to a residual taste for certain artists socially sanctioned for non-musical reasons. As various generations have risen to the editorial reins at cultural tastemakers, one begins to see re-evaluations and defenses of their youthful enthusiasms, and the likes of Phish and Blink-182 enter the canon. No-one will let you, anymore, get away with expressing disdain for the pop tastes of teen and tween girls. That’s all fine. But I’m here to say that you can still, in 2026, get mocked for being an Ani DiFranco fan, and by people who otherwise make a point of situating their taste outside the straightjacket of hipster cool. Why?

I realize that by using Phair as a foil I’m sidling into doing something I know you’re not supposed to do in serious criticism: comparing two female artists based on a demographic rather than artistic similarity. But if you were the 1995 equivalent of these Bard College students—smart, artsy, middle-class (at least), sexually fluid and gender-ambiguous, though (at that time) probably identifying as female—you had copies of both Whip-Smart and Not A Pretty Girl.

But Phair is easier to assimilate into a canon, both structurally and as an artist. She was a creature of Chicago indie rock in the 1990s, as close to the beating heart of cultural capital as it got. Canonic albums on Matador Records, ditto; then major labels. The songs were about living among the young men of that scene; the narrative of its birth inextricable from the men who inspired it and the men who helped it get made and heard—for all its subversive feminism, Guyville (“everything I wanted to say to the guy I had a crush on”) doesn’t even sniff the Bechdel test. Phair was, not for nothing, explicitly heterosexual: you have to think that the number of times the blowjob lyric and “I’ll fuck you ‘til your dick turns blue” were quoted in reviews bears some correlation with the titillation of some of the reviewers, and how seamlessly they could imagine themselves the object.

Not so DiFranco. Not that she couldn’t express romantic vulnerability, or be capable of a sly blowjob joke, but you certainly never felt like she was anything but in command, actively interrogating her polymorphous entanglements, gleeful but tough and clear-eyed about her agency and responsibility in the name of a vibrant life:

Everything I do is judged
And they mostly get it wrong
But oh well
'Cause the bathroom mirror has not budged
And the woman who lives there can tell
The truth from the stuff that they say
And, she looks me in the eye
And says "Would you prefer the easy way?
No? Well, okay, then ...
Don't cry.”

One was skinny, blond, in jeans, dresses, heels; the other, shaved head, dreadlocks, nose ring, cargo pants and combat boots. One embedded in the ironic cool-kid world of indie rock (and engaged, even combatively, with the most canonic classic rockers); one who emphatically identified with the square, earnest, unhip folk lineage of Pete Seeger and Utah Phillips—even spoken-word poetry. (Later, musical theater—she played Persephone in Hadestown, whose writer, Anais Mitchell, received crucial early support from Righteous Babe, who released the original Hadestown album.) One who emphasized her amateurishness as a singer and guitarist; the other, a virtuoso and confident bandleader.

The conventional wisdom goes that both lost the plot, or fell from audience and critical grace around the turn of the 21st century. DiFranco’s audience, if I can trust my perception from the time, objected to her increasingly normative personal life as a wife and mother; her music—like that of her occasional friend and collaborator Prince—increasingly embraced lightly funky muso jamming. (Like Prince, there’s a substantial latter-day catalog whose nuggets take some more panning but the strain is by no means depleted. Like Prince, too, the live shows remain exceptional; like her cultural contemporaries Pearl Jam, the audiences appear mostly composed of the round-one fans and light on newer converts.) In any case, she seems to have become overwhelmed by the weight of expectations, and by a punishing touring schedule. Phair embraced full-on Pop with a capital P, working with professional songwriters, and wrote for TV. When Pitchfork has offered multiple mea culpas for its excoriation of this phase in Phair’s career, it only underscored that her path—home demos to laptop pop, even the half-baked desktop-screenshot artwork—looks a lot like the career paths of many 21st-century internet natives. And when it came time for anniversary victory laps, the full force of the music industrial complex was there to support it.

I think that’s one of my takeaways from this comparison: that you can have time in the critical and commercial wilderness, but if you’re basically not a joiner in the industry sense, you don’t have the ready-to-hand infrastructure—label, publicity, journalists—to support a comeback/redemption narrative. To put it rather crudely, there’s a cool kids’ table, Phair has a seat at it, and that still makes a difference. (See also the recent reappraisement of the Lilith Fair, which may have been a punch line in its time but was by no means out of the mainstream of commercial taste—DiFranco wasn’t a part of that scene, either.)

The other is that for all the elite redemption of the musical tastes of tween and teen girls—which happen to conveniently overlap with the peak commercial interests of the industry—no amount of cultural capital is about to accrue to the tastes of middle-aged moms. The earnest college girls of DiFranco’s 1990s crowds didn’t go on to careers in professional cool, as cultural tastemakers in New York and Chicago; they’re the people organizing the youth soccer leagues, school boards, and small-town political protests: the thankless, unglamorous work that is the fabric of mundane American communities.

DiFranco’s 2019 memoir winds up in the early 2000s, just after her cultural peak—that is, when, for someone like me, just when things are getting interesting. Last year’s documentary 1-800-ON-HER-OWN (now streaming) picks up later, around 2019. (A new book is upcoming.) I want to know more about that decade, roughly, between her divorce in 2003 and the split from her longtime manager and business partner in 2017. (A ruinous real-estate investment in her Buffalo hometown, in an over-idealistic attempt to revitalize its cultural fabric, seems to be a major plot point.) Middle age— the decades between the initial rocket-booster stage and, hopefully, “rediscovery” as late-career elder—is a fraught time for artists. The primary emotional ambience of the documentary is physical and spiritual exhaustion, in stark contrast with the intoxicating energy of the earlier footage; since a lot of that exhaustion seems tied to the vampiric demands of fans on her time and privacy (albeit that’s an occupational hazard for life-as-art/art-as-life songwriters), I feel guilty for even expressing that curiosity.

But enough about DiFranco the cultural figure, even DiFranco the songwriter. When I saw her in Troy in 2023, for the first time in decades, I was struck anew by her musicianship—an extraordinary guitar player, with that unique style simultaneously percussive and melodic, which seems to involve electrical-taping picks to each finger of her right hand. (You’d have to think it’s interesting that DiFranco, Mitchell, and Armatrading each developed highly individual ways of playing such a canonically phallic instrument, with such encrusted norms and standard techniques. In the documentary, DiFranco expresses frustration with the musical limitations of folk music—“I hate folk songs…all the ways you can go between C, G, and D”—even as she’s on the way to play a Woody Guthrie singalong at a protest, and repeatedly embraces folk music’s self-imposed burden of speaking to politics.) She’s been good at keeping bands together (both the Sara Lee/Andy Stochansky lineup of the imperial years, and the recent configurations of which bassist Todd Sickafoose is the mainstay); she seems be a generous bandleader who inspires loyalty, interested in jazz-like musical conversation.

I’m once again thinking about the comparison to Prince. DiFranco herself has talked frankly about the ways in which she felt more of a kinship with Prince than, for example, Bob Dylan. Both sacrificed a good deal—in money and cultural cachet—for idealistic independence, both personal and artistic. Both used that independence in the service of deep and largely unexplored late catalogs. If the price of that independence may have seemed—may still seem, to DiFranco—Pyrrhic in the short and medium term, they’re redeemed when we pay them the respect of our attention.

Current reading: Rose Macaulay “Pleasure of Ruins” (1953): a travel book presenting a taxonomy, then tedious inventory, of ruins (cities, castles, temples, false ruins, the then-new postwar ruins of modernity, and the Ruinenlust and Ruinenschmerz of those who seek them out for contemplation. Intriguing concept but ultimately pretty repetitive as a reading experience.