“When the Pawn…” by Fiona Apple | Album Review

I revisit Fiona Apple’s incredible, unshakeable late-90s sophomore record.

This album review revisits Fiona Apple’s late-90s sophomore album, a no-holds-barred rebuke of what you (and she) think you know.

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Genre: Singer/Songwriter, Alternative, Rock

Label: Epic

Release Date: November 9, 1999

Vibe: 💔

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👉 Click the GIF to stream the album on your favorite platform

Good writing is occasionally vulnerable so it can make the words feel relatable. It offers up observations that, in a vacuum, ring true enough to make you nod your head silently in agreement or, in rare cases, consider your worldview a little differently than you had before. But good writing has its limitations. It’s not great writing. It’s not personal enough to throw you off your axis. It doesn’t hold a mirror up to the kinds of uncomfortable truths that keep you up at night. It fails to reach the point where, even if the writing describes scenarios divorced from your daily life, it hits you like a ton of bricks because you recognize the struggle. The ugliness, even. It reaches into the deepest, often darkest corners of someone else’s psyche and teaches you a thing or two about your own. That’s what great writing is, and Fiona Apple’s sophomore album, When the Pawn…, is full of incredible passages.

A child prodigy who began composing her own songs at age eight, Apple’s upbringing was marred by pain. At 12, she was raped outside of her residence in Harlem, which led to her suffering from panic attacks walking home from school and developing an eating disorder. "What was really frustrating for me was that everyone thought I was anorexic, and I wasn't,” she said. “I was just really depressed and self-loathing." She’s also struggled with OCD, depression, and anxiety. I bring these facts up because I think When the Pawn… is as much a record about mental health—or, more accurately, resilience in the face of the trauma that impacts it—as it is a sly rebuke of her public persona. Following the success of Tidal, which sold three million copies largely on the back of the widely misunderstood hit single “Criminal,” Apple was labeled as precocious at best. Some were far more derogatory with the language they used.

In June 1997, she stepped on stage at the MTV VMAs and delivered a memorable middle-fingers-in-the-air acceptance speech:

“So, what I want to say is, everybody out there that’s watching, everybody that’s watching this world? This world is bulls***. And you shouldn’t model your life about what you think that we think is cool and what we’re wearing and what we’re saying and everything. Go with yourself. Go with yourself…And it’s just stupid that I’m in this world, but you’re all very cool to me so thank you very much. And I’m sorry for all the people that I didn’t thank, but man… it’s good. Bye.”

Today, that would be a viral online moment where she’d be (rightfully, I think) praised for her candor. At the time, she was perceived as an ungrateful shrew whose nihilism was deemed unbecoming of a young woman gaining momentum in the music industry. A few months later, Spin published an unflattering cover story that described her, among other things, as “a pop star trapped in the body of a pretty teenage girl.” It was not an uncommon observation at the time (this was back when it was fashionable to start countdowns to when underage female celebrities would “become legal”), with the Grey Lady publishing that Apple came off as "a Lolita-ish suburban party girl.” Amid the mounting backlash, the singer-songwriter did the unthinkable: she spoke her unpopular truth with even more conviction and venom, even though I’m sure she knew she’d be raked over the coals for doing so. I certainly wouldn’t have had the guts to do what she did or express it so profoundly on the page.

It starts with the title, which runs 444 characters and, at the time of the album’s release, set the record for the longest ever. It was, predictably, dismissed as a mindless appeal for attention, but, upon closer inspection, it reads as a self-motivational speech that could only come from Apple’s brand of unflinching honesty:

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

The record itself doesn’t ease you into its headspace. Against Jon Brion’s lurching, percussive production, Apple’s voice surges with palpable, coiled tension. She’s plainspoken about her pessimism, choosing the comfort of that worldview over a love that, on the surface, has nothing inherently wrong with it. “It’s true, I do imbue my blue unto myself,” she admits at one point. “I make it bitter.” For a song about the risks involved in opening oneself up to love, it’s striking how playful its energy is, coming off as a Vaudevillian late-90s mishmash of heavy piano chords, thick snares, and distorted guitar noodling. Later on, she fleshes out the narrative arc on “Love Ridden,” a haunting ballad that still ranks as one of her most lyrically devastating works. Its second verse is one of the most beautifully rendered evocations of heartbreak I’ve ever heard:

Nobody sees when you are lyin' in your bed
And I wanna crawl in with you but I cry instead
I want your warm but it will only make me colder when it's over
So I can't tonight, baby

If I had to pick one song from this record that encapsulates Apple’s genius as a songwriter, it’s “Paper Bag.” It’s a pop song, technically, but one wearing a trench coat full of secrets. It’s airy, jazzy production masks the brilliance of its central metaphor, where hope’s only logical denouement is disappointment. Her crush’s refusal to satisfy her infatuation, due at least in part to him knowing that Apple is “a mess he don’t wanna clean up,” becomes a cruel, cosmic joke in her eyes. The track’s conceived and executed so masterfully that you don’t realize how melancholic it is when you first hear it. “He said, ‘It’s all in your head,’” she sings later on. “And I said, ‘So’s everything,’ but he didn’t get it.” It’s a laugh-out-loud line, one of several, that gets more profound with each new listen. Yet, somehow, it never comes across as cloying or overly self-pitying. Just embarrassingly human, making it an excellent example of that reflective dynamic I referenced earlier.

Then there’s “Fast as You Can,” a standout for an entirely different reason: its rhythmic complexity. It bends time through repeated time signature changes, fueled by Matt Chamberlain’s performance on drums and producer Jon Brion’s anxious-sounding production. Known for his left-field orchestrations, Brion worked closely with Apple to imbue this and every other track with an organic, lived-in quality that matches the intensity and volatility of her lyrics. “All I did was to heighten pre-existing things", he said later. "In terms of the color changes, I am coordinating all of those, but the rhythms are absolutely Fiona's.” At its center, she twists and turns unpredictably, presenting herself as both narrator and subject. Living in that grey area between self-awareness and self-deprecation, “Fast” is less a song than it is a mood swing committed to tape. The instability you hear would later be co-opted as an aesthetic by artists like Billie Eilish and St. Vincent. It’s experimental pop that, through movement, not just words, communicates a universal sentiment.

When the Pawn… closes with “I Know,” a calm catharsis after the storm of emotion you’ve just heard. The track strips everything down to a sigh. Apple’s voice is barely above a whisper, opining about loving someone with eyes wide open and how, even if the spark fades after however much time, the part of you that loved and lost will never disappear completely. There’s no big crescendo or reaching for some kind of cinematic payoff. Instead, she delivers the final verse with the tender care of someone cradling something so fragile it’s doomed to break, no matter how careful you are. In this instance, love is a tool of destruction or liberation, depending on your point of view. That Apple never overtly picks a side is the absolute right choice artistically, even if it doesn’t offer closure for the listener.

In 1999, right before this record was released, her label panicked. There was no “Criminal” follow-up (though I’d argue that “Fast as You Can,” the eventual lead single, is a better song in basically every way), no pop polish. They wanted her to reconsider and re-record, and, of course, you know this before I even say it, she refused. With hindsight, it’s clear she was right, as well as ahead of her time. It’s not simply her most complete record, her best in a catalog full of exceptional work, but it’s also her most daring. Many artists still shy away from reclamation projects this bold and in-your-face, fearing that honesty can’t be art and rage can’t be poetry. What makes When the Pawn… endure is the very emotional architecture most run from. There’s no redemptive arc, no sugarcoated catharsis. Just the grief, the grit, the work of naming the wound before it heals over. Apple has argued publicly that women shouldn’t need to shrink into likability to be heard. Her voice, raw and precise, has never sought that kind of approval. Maybe the lesson is that neither should you.

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What’s your favorite Fiona Apple song? Shout it out in the comments.