Ani DiFranco burst out in 1990 with a self-titled album of complex, beautiful, haunting songs characterized by a unique guitar picking style and an evocative lyrical style. Ever since, she’s spent three prolific decades experimenting with an impressive array of musical styles and themes. Her peak probably came during the late 1990s–the period most heavily represented on this list–but there’s great music everywhere along the whole path.
You’ll also notice the number of live tracks on here. DiFranco is notable for being the rare artist who is better live AND for whom that superiority actually manages to come across in recordings. In fact, I’d go so far as to suggest that Living in Clip is on the shortlist for greatest live albums of all time. It’s jam packed with great songs, most of which are the definitive takes, and almost all of which are better than their studio counterparts. Seriously, everyone should own that record.
10. Talk to Me Now (Ani DiFranco)
So many of her great songs deal with the small ways in which femininity is weaponized. It’s an interesting feature of her work, to engage seriously with the question of how patriarchy produces standards of attractiveness the hurt everyone. The way that presenting as abnormal—a shaved head, tattoos—generates danger, which is different but not separate from the dangers that come from presenting as conventionally beautiful.
Here, all she wants to do is walk around her own city, and get on with the business of her own little life, and is faced with endless harassment from men who think their attention is inherently complimentary. Men who will “stop at nothing once they know what you are worth.” The defiance in her voice is cathartic, even as you are forced to recognize that every single battle must be fought over and over again. Patriarchy doesn’t present itself as a Big Bad, to be slapped down once and then consigned to the dustbin of history. It is everywhere, ubiquitous, a constant hassle. And so she sings her strength, just to keep herself afloat.
9. Gravel (Little Plastic Castle)
While I don’t have any of her truly experimental and weird stuff on this list, I at least wanted to make sure to include Gravel, as a reminder that when she wanted, she could unleash some blistering rock and roll. It’s also a helpful corrective for anyone who ever doubted that an acoustic guitar could spit fire.
8. Untouchable Face (Living in Clip)
Unrequited love is one of the classic themes of popular music, but a vanishing few that manage to convey the experience so precisely or with such care. It features a lot of wry self-deprecation, but also a lot of vulnerability, all packaged with a simple, warm guitar line.
In this case, the difference between this version and the studio recording is primarily in the balance between the humor and the pathos. The studio version feels just a bit too heavy with the weight of feeling; this one is a joke shared between friends, who laugh because they know the pain is real but they also know how ridiculous it all is.
7. Angry Anymore (Up Up Up Up Up Up)
The first time I saw her play live was on her tour following the release of this album. This song was the highlight of that show, and remains one of my favorite concert memories. She did it acoustic and solo, and all of its tenderness and generosity came across perfectly.
It’s a song about growing up and coming to understand yourself better. And it’s a song about how that maturity can reshape your understanding of the events that drove your childhood. To see your parents as human beings, with all the attendant imperfections, and to love them even more for those limitations.
I’ll refrain from quoting too much as I discuss these songs, because it could easily get out of hand. But I can’t let this one go past without noting one of my all-time favorite verses:
She taught me how to wage a cold war with quiet charm
But I just want to walk through my life unarmed
To accept and just get by like my father learned to do
But without all the acceptance and getting by that got my father through
The amount of depth that she manages to pack into just a few words here is just astonishing. This is an entire short story composed in less then fifty words.
6. Letter to a John (live)
This is a grim song, particularly the third verse (“I was eleven years old, he was as old as my dad. And he took something from me, I didn’t even know that I had”), but it refuses to let the pain become overwhelming. Instead, it explores the way that violence and desire are intermixed, and the ways that women find strength both through and against this effect. And so it’s certainly not an empowerment anthem—she’s wise enough to understand the danger of trading on that sort of narrative—while still helping to show how resilience can grow into something more than just ‘hanging on.’
As with most of her songs, there are quite a few versions of this one floating around, all of which give a slightly different flavor. This one is my favorite. I’ve never actually been able to figure out where it came from, though. If anyone knows, let me know!
5. Marrow (Revelling/Reckoning)
This is Ani at her biggest and brightest. As with many of her great songs, it’s poised carefully between several different and powerful emotional currents. There is joy here (it comes from the ‘Revelling’ side of the album, after all), but also a deep wellspring of pain. We struggle to stay afloat in the stormy waters, desperate to forget all of the things that hurt us, and therefore doomed to repeat them over and over again.
Back in 2009, I wrote a post about the poem that was read at Obama’s inauguration, complaining that it offered platitudes in place of politics, and in its timidity failed to live up to the moment. And I noted that this was more a flaw in the form of the inaugural poem than it was a failure of the poet. It is hard to speak truthfully to the hope embodied by a new dawn without coming to terms with all the suffering that continues to remain hidden in the dark of night. That’s why inaugural poems—which owe too much to the grandeur of the moment—are doomed to failure, while something like this song—which is free to speak honestly about just how deep we remain trapped by the mistakes of our past—would be far more appropriate to the occasion.
4. Present/Infant (Daytrotter Session)
In so many ways, music is a young person’s game—driven by the unwavering certainty of self that so often defines youth. When we are young, we race over the horizons, driven by the need to discover what else might be out there. We seek new challenges, in the hopes of showing the world what we might yet become. As we grow older, the horizons grow more distant, and we increasingly come to understand that we were often running away from ourselves as much as we were running toward the horizon. There comes a moment of reckoning, when we ask whether we can ever be comfortable in our own bodies, in the horizons that we have marked out for ourselves. When we begin to see ourselves not as isolated individuals, but instead as objects reflected back by the world that we’ve created. And we are forced to ask: does this make me happy?
In this song, we get a sort of answer, as we encounter the precociousness of youth growing into maturity, and as we find the artist learning how to grow into herself. Finding a way to dwell with her fears—accepting them without letting them rule her. Discovering that there’s still room to thrive even as she enters a new phase of life. Coming to see that beauty is what we share in our quietest moments.
3. Little Plastic Castle (Little Plastic Castle)
This is the first song of hers I ever heard. The moment the horns burst onto the scene, I was completely hooked. It’s a piece of unbridled joy, a statement of intent. Only after I dug into the rest of her catalog did I fully understand how this song fit into the arc of her career, the slyness of the lyrics, the perfect blend of ironic detachment and exultation that it embodies.
2. Both Hands (Ani DiFranco)
It’s raw, lovely, heartbreaking. Even now, after all these years, it still shocks the system. The way it creeps over you, the way the guitar fills you and then falls away. The way her voice cradles you, fills you with a swell of empathy that is almost impossible to bear. And all you can do is wonder that this young woman—just 20 years old when it was released—could understand so much, could see so deeply inside. It’s an astonishing piece of music.
1. 32 Flavors (Living in Clip)
There aren’t many songs that leave me totally defenseless, no matter how many times I hear them. This is one of the few. A defiant stare. A blushing cheek. A prayer sent upward into the unyielding heavens. A poem written in the stars.
11. Swan Dive (Little Plastic Castle)
12. Napoleon (Living in Clip)
13. Hello Birmingham (To the Teeth)
14. Fire Door (Living in Clip)
15. Buildings and Bridges (Out of Range)
16. Not a Pretty Girl (Not a Pretty Girl)
17. School Night (Revelling/Reckoning)
18. Tis of Thee (Up Up Up Up Up Up)
19. You Had Time (Out of Range)
20. Fixing Her Hair (Imperfectly)