“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”
By 1999, Fiona Apple was done with the noise. After the breakout success of her 1996 debut Tidal, she became a media sensation, scrutinised for everything but her music. Her bold 1997 MTV Video Music Awards speech, where she called out the industry’s fakeness, was a shot across the bow of celebrity culture—and the press didn’t take kindly to it. Instead of focusing on her artistry, the media dissected her vulnerability, labeling her as “fragile”, “insufferable” and “overly dramatic.” Male artists could rage, mourn, or break down with no consequence, some were even celebrated for it, but for Apple, expressing her pain in public was something the press couldn’t forgive.
The fallout from that moment hit Apple hard, and the double standard she faced was glaring. She wasn’t just dealing with the music industry’s entrenched misogyny, but also the wider cultural tendency to dismiss women’s emotions as melodramatic. Apple’s public outbursts became tabloid fodder, overshadowing her real work. This tension, coupled with the backlash from her speech, laid the foundations for When the Pawn…— a deeper, more focused work, that hit back like a swinging wrecking ball, smashing through her critics and dismantling the pattern they’d trapped her in.
“[SPIN] screwed me from the beginning. They knew what they were going to do with the story and it really didn’t matter what I said…” Fiona Apple via Washington Post 1999.
The album’s title alone—a sprawling, defiant 90-word poem Apple wrote in response to a scathing cover story in SPIN Magazine —sets the tone for what listeners could expect. Some dimissed it as long and pretentious. But it was more than just a title. It was a manifesto, a clear signal that she wasn’t going to be boxed in or silenced. It was her way of taking control, making it clear that her story—flawed and authentic—would be told on her terms, daring critics to look beyond the headlines and actually listen.
Recorded at Ocean Way Studios, When the Pawn… became Fiona Apple’s reclamation of self, not just a catharsis. It tore up the neat, marketable version of her critics had latched onto. The now-legendary story of her breaking down in the studio bathroom, feeling estranged from her own lyrics, encapsulates the emotional weight of the project. Jon Brion, her producer and collaborator, gently knocked on the door, offering his quiet support: “Yeah. But can I cry some more first?” she replied. That raw vulnerability wasn’t a moment of weakness—it was the fuel for the album’s power. Apple also had more artistic control, and felt more confident in expressing what she wanted from the recording process. Brion’s production did more than just shape the sound; it amplified Apple’s authentic emotions, transforming her vulnerability into lush, complex and genuinely affecting songs.
Musically, When the Pawn… shattered expectations. In contrast to the slick, commercial pop and R&B that dominated radio in the late ‘90s, When the Pawn… was something else entirely. It was messy, it was angry, and it was emotionally complex. Apple embraced the messy, uncomfortable parts of herself that the media had weaponised. Some songs on the album, like ‘Fast as You Can’, are exercises in controlling this turbulence. With Brion’s orchestration—layering strings, brass, and intricate piano—Apple created a world where her emotional volatility is laid out in relatable detail, becoming something to celebrate and accept, not hide. The jazz-inflected verses of ‘Fast as You Can’ give way to explosive, roaring choruses, as Apple warns anyone willing to love her that they’re signing up for a rollercoaster ride through her psyche. “I let the beast in and then/ I even tried forgiving him, but it’s too soon / So I’ll fight again, again, again, again, again”. The music video, directed by her then-partner Paul Thomas Anderson, spirals with the same frenetic energy, visually reflecting Apple’s refusal to be tamed.
It’s worth noting the broader context of When the Pawn… and how Apple was part of a wider wave of women artists pushing against the constraints of the music industry. Alongside her, artists like Alanis Morissette and later Lauryn Hill broke similar ground. Morissette’s Jagged Little Pill gave a platform to rage and vulnerability, while Hill’s The Miseducation of Lauryn Hill boldly addressed race, motherhood, and spiritual introspection. Both faced backlash for their emotional transparency, much like Apple. But Apple’s approach was even more introspective—she leaned into the discomfort, shed the “sad-girl-singer-songwriter” label often pinned to her and expanded her sound. Her signature husky voice now weaving in a broader range of influences—jazz, swing band and pounding, heavy percussion. All of this built towards a sound unmistakably her own, revealing a balance between fragility and resilience; a vulnerability that felt precarious, yet undeniably strong.
Listen closely, and you’ll also hear threads of dark, self-aware humour running through When the Pawn…. On ‘A Mistake’, she practically revels in the self-sabotage, the fun of embracing one’s failures: “And when the day is done, and I look back / And the fact is I had fun, fumbling around.” Then there’s ‘Paper Bag’, one of the album’s standout tracks. Beneath the upbeat, jazzy veneer, the song tells a story of misplaced hope, with Apple mistaking a paper bag for a dove—a metaphor for her tendency to want more in things and people than reality can offer. “Hunger hurts, but starving works,” she sings, admitting that she’s “a mess he doesn’t want to clean up”. It’s a line that strikes like a knife, equal parts sorrow and humour, as she confronts her tendency to fall short of her own hopes.
Elsewhere on When the Pawn…, tracks like ‘Limp’ and ‘Get Gone’ capture Fiona Apple at her most furious, tearing apart the male gaze through which she was viewed after Tidal. Apple confronts the “Lolita” tag head-on, daring anyone to objectify her. “You fondle my trigger, then you blame my gun,” she snarls in ‘Limp’, cutting through with sharp, biting imagery. Then, with palpable scorn, she mocks the way her pain has been fetishized: “You wanna make me sick / You wanna lick my wounds / Don’t you, baby?” ‘Limp’ doesn’t just simmer with anger—it builds to an explosive release, with Apple’s voice swelling alongside a dense, orchestral arrangement that mirrors her mounting frustration.
With biting lyrics and relentless determination, ‘Get Gone‘ lays bare her frustration and exhaustion in a toxic relationship. The song’s driving rhythm mirrors her urgency to break free, while lines like “I do know what’s good for me” and “It’s time the truth goes out – he don’t give a shit about me” reinforce the theme of self-empowerment that runs throughout the album. ‘Get Gone’ isn’t a plea for release—it’s a middle finger to an abuser, marking a critical moment where Apple seizes control of her narrative. Again, she pushes back against the critics, particularly the men who labeled her as emotional, unstable, even crazy – reclaiming those very labels in the song. What she lays bare here is profound: her so-called “unhinged” behavior isn’t a sign of weakness; it’s raw, unfiltered honesty. She reframes “unhinged” as a form of genuine expression—brutal, direct, and anything but the shallow “bullshit” the industry so often peddles.
For all its anger and volatility, When the Pawn… also offers moments of exquisite stillness. ‘Love Ridden’ strips everything back, its delicate piano arrangement carrying a quiet resignation as Apple reflects on a love that’s slipped away beyond reach: “No, not ‘baby’ anymore / If I need you, I’ll just use your simple name.” It’s a heartbreaking acceptance of the finality of loss, and Apple delivers it with a tenderness that lingers long after the song ends. Again on ‘To Your Love’ , Apple wrestles with her difficulty in accepting love, likening it to a disease. She alternates between yearning for love and rejecting it due to her internal pain, ultimately reflecting her struggle to reconcile her emotional desires with her sense of unworthiness. This tension plays out in the constant key changes and the fluidity of the track, enhanced by Brion’s intimate understanding of what could convey this complicated cocktail of desire and fear.
This intimacy culminates on ‘I Know’, the brilliant final track on When the Pawn… Apple offers us an intensely personal few minutes that are both beautiful and difficult to hear. Over sparse, melancholic piano chords, her voice sounds both loving and resolute. There’s a finality and acceptance in her words that melts through any cynicism. In interviews, Apple has described the song as a meditation on unconditional love and patience, even in the face of inevitable disappointment. It’s poetic and moving, with a melody that swings and sighs with each realisation:
“And I will pretend / That I don’t know of your sins/ Until you are ready to confess / But all the time, I’ll know I’ll know / And you can use my skin to bury secrets in”
The final chord hangs loosely, expectantly in the air, and the last line is set up, but left unsaid. It’s a perfect close to an album that refuses to resolve neatly.
If there’s a golden thread running through When the Pawn…, it’s Fiona Apple’s relentless pursuit of truth—her truth. She was, and has always been ahead of her time. Even now, there’s subtle media cynicism for addressing emotional and mental health struggles—issues that the music industry is still having difficulty with today. In a world where artists like Billie Eilish, Mitski, and Taylor Swift are scrutinised for their emotional transparency, When the Pawn… feels both timeless and necessary. Apple’s refusal to conform, her willingness to embrace her pain and chaos, was revolutionary then, and it remains so today. In many ways, she set the stage for the kind of unflinching honesty we now see celebrated in modern music, though her battles with the media’s double standards were far more intense.
When the Pawn… wasn’t made for commercial success, and yet, despite a slow start, it found some anyway, debuting at number 13 on the Billboard 200 and eventually going Platinum. But for Fiona Apple, the numbers were never the point of When The Pawn…. Twenty-five years on, the album’s real legacy is its defiance—a lesson to aspiring artists that raw honesty and authenticity, however messy they are, will always outlast a perfect image.
SPIN ran another cover feature on Apple in 2000, where she reflected on what it means to be a true artist in a shallow industry:
“It means a lot to me that I write my songs. And people who don’t write their songs better be fucking really great performers and really have a fucking voice. Otherwise, why are you there?”
