Depth is the greatest of heights

A quick thank you to Fiona Apple for When the Pawn… now 20 years old.

Christopher May
Nov 5 · 4 min read

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.

Fiona Apple was born a fortnight after me. I’ve always felt weirdly protective of her. It was a privilege to have a singer-songwriter of this calibre appear right at the time I was trying to find my own voice. The idea of “Generation X” always sat uncomfortably on me, like a hand-me-down suit that was one size too large for me. We were supposed to be all about confessional authenticity and radical resistance of shame, but you still had to buy into it with the right magazine, the right movie tickets, the right pair of Cherry Docs. Amongst all that posing as not-posing, reciting the spontaneous, I wasn’t even sure who my cohort were. When Fiona Apple came along, I felt like I could finally locate my generation, and locate myself.

Falling apart in October 1999 as I did, and ending up in an anorexic body haunting my parents’ house, the release of Fiona Apple’s “When the Pawn…” was an unexpected suit of armour at a very vulnerable time for me. It was literally a dark time — I became something of a shut-in because I couldn’t walk around without getting dizzy and slumping against a door-jamb, so I was inside every day, and awake most of the night. It was all Tungsten lights, bedside lamps and the orange ember at the burning end of a cigarette or an incense stick.

Sometimes the right album comes along at the right time, I guess. Illness had completely deconstructed me by November 1999, and there isn’t much music you can stand when you’ve lost your identity, lost even your belief that it’s possible to have an identity. “When the Pawn…” was not medicine. It wasn’t like each rotation was making me feel better about myself, or better about life. It didn’t make me cheer up and smile.

It was more like a syllabus. I learned the songs, and learned them as a new taxonomy of emotions, a new way of describing experience. It made me feel less ashamed of being angry. It made me feel less ashamed of being destroyed. And I was angry and destroyed. I won’t say it shed light on everything, but it taught me to see in the dark a bit better.

From the swaggering cabaret of On The Bound to the maudlin vaudeville of I Know, the album is a disciplined and raunchy piece of heartbreak theatre. Moments of it involve the literal suspension of breath, from Fast as You Can’s single breath syllabic “fast-as-you-can-baby-wait-watch-me-I’ll-be-out-fast-as-I-can-maybe-late-but-at-least-about-fast-as-you-can-leave-me-let-this-thing-run-its-route-fast-as-you-can” to I Know’s audaciously protracted “So for the time being, I’m being patient.”

Last month on Twitter I saw a cute little singer-songwriter challenge, “Pick your fighter” with images of Joni Mitchell, Kate Bush, Tori Amos, and Fiona Apple all holding swords in promotional images.

It’s a great conceit. As ever, with these Twitter challenges, I spent an embarrassing amount of time and thought on it. I grew up listening to Joni Mitchell. Kate Bush was my first intimacy with pop music (I’ve written about it here). And Tori Amos was my 90s and 00s obsession, the artist I’ve listened to most in my life (every week! For decades!).

But my answer to “Pick your fighter” was, and is, Fiona Apple. Her vulnerability reminds me of my own. Her anger reminds me of my own. Her fandom are a fascinating and diverse group of reconstructed emotional soldiers.

And apart from that, I just really feel like Fiona Apple was experiencing some really dark shit at around the same time I was. The environmental component of her apocalypse was the same as mine — Gulf Wars, Tabloid Tyranny, Computer Crisis, Globalisation, Body Shaming, Gender Backlash, Consumerism — I feel like she has met with many of the beasts that came for me, and like me, she barely survived. Maybe I don’t want her for my fighter. Maybe I want her for my coach, or my friend. I don’t know. The mechanisms of fame are degrading to everyone, so it sometimes feels dumb comparing artists. Maybe we’re all part of the one big artwork anyway, you know?

But still, I’m grateful for “When the Pawn…” the album that came that in the darkest time of my life, and braved the dark with me. For all its campness, it has always seemed to me to be a properly authentic album, coming at the end of a decade when every music corporation was trying to find a way to simulate authenticity for profits.

Happy 20th Birthday, When the Pawn. You survived that shitty century, and you closed the curtain on it.


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