Album Anniversaries: 20 Years of Fiona Apple’s ‘When the Pawn…’

Fiona Apple’s sophomore LP expanded her sonic palette and proved she was more than just a “Criminal.”

In Album Anniversaries, writers honor their favorite aging albums and their subsequent legacies, revealing which projects have stood the test of time.

Written by Carys Anderson

 
Photo courtesy of Epic Records

Photo courtesy of Epic Records

 

When Fiona Apple declared in her acceptance speech at the 1997 MTV Video Music Awards that “this world is bullshit,” a floodgate of eye-rolls opened that proved hard to close. Here was a clearly talented young woman — her 1996 debut Tidal sold three million copies, won her the title of MTV’s Best New Artist, and showcased songwriting abilities beyond her 19 years — but the speech was seen as pretentious. To some critics, so was the music — too wordy and too jazzy, Tidal was written off as the try-hard ramblings of a teen girl. 

Many took Apple’s looks more seriously than her music. Lounging in her underwear among anonymous limbs in the video for her breakout single “Criminal,” a song that starts off with the announcement “I’ve been a bad, bad girl,” made her an easy target. Her admitted anorexia became a talking point as well, especially in the era of “heroin chic” fashion. Even Jon Pareles, who has been the chief popular music critic at The New York Times for over three decades, opened his 1996 review of an Apple concert with a detailed description of her “full lips” and “pierced navel” — but only after reminding readers of her young age. 

Three years after Tidal, a jazz album of private ruminations from a precocious unknown, Apple returned on Nov. 9, 1999 with When the Pawn… (whose full title is 90 words long). No longer unknown, Apple possessed the confidence of a star and the anger of one whose fame came, partially, from criticism. 

If Tidal is a sigh, When the Pawn… is a stomp. Rock instrumentation and more concise arrangements deliver Apple’s perspective on a wave of hooks, more direct responses than contemplative musings. From the slow, pounded chords of opener “On the Bound,” Apple’s confidence, in both her musicianship and her understanding of herself, is clear. “It’s true, I do imbue my blue unto myself / I make it bitter,” she chants. The melodies keep unfurling from there. “Maybe some faith would do me good,” she wonders, conscious of her tendency toward darkness. It’s a theme she leans into throughout the album.

Apple spends first single “Fast As You Can” advising a lover that he wants nothing to do with her for this very reason: 

Oh darling, it’s so sweet

You think you know how crazy

How crazy I am

You say you don’t spook easy

You won’t go

But I know

And I pray that you will

Exploring one’s faults is rare in pop music, and it was new for Apple at the time. But after this introspective  record,being ill-equipped for relationships became a classic Fiona trope. 

The music behind Apple’s vocals in “Fast As You Can” was an equally exciting departure from the production of Tidal. Apple’s words slip over each other on top of a skittering trip-hop beat and a vacillating piano riff. “I may be soft in your palm / But I’ll soon grow hungry for a fight / And I will not let you win,” she taunts in a sing-song voice. “My pretty mouth will frame the phrases that will disprove your faith in man.” She had to pick up the pieces in “Criminal”; now Apple opts to warn everyone of her character to avoid the same destruction. 

“I went crazy again today,” Apple reports in “Paper Bag,” a whimsical piano number. Backed by a chorus of horns, she concedes, “I know I’m a mess he don’t wanna clean up.” Tidal’s intellectual lyricism often required a reading of the liner notes to grasp, but the directness of lyrics like these won critics over — they’re evocative on first listen. Resigned, Apple sighs in the chorus: “Hunger hurts but starving works when it costs too much to love.” 

Despite this maturity, Apple still loves a sweeping statement. “He said ‘it’s all in your head’ / And I said ‘so’s everything,’ but he didn’t get it,” she recounts in “Paper Bag.” It’s these hyper-aware confessionals that define Apple’s work.

 
Photo courtesy of Dave Allocca/DMI/The LIFE Picture Collection/Getty Images.

Photo courtesy of Dave Allocca/DMI/The LIFE Picture Collection/Getty Images.

 

When the Pawn… is perhaps the most diverse album of Apple’s catalogue. The swaggering “A Mistake” is the artist at her coolest. Synthetic slides broaden its atmospheric palette further, as Apple rebels against her standard obedience: 

I’m always doing what I think I should

Almost always doing everybody good

Why?

And in an understated, but still boastful, voice, Apple sneaks in one of her slyest lines: “And if you wanna make sense / Whatcha lookin’ at me for / I’m no good at math.” 

Apple’s music has always been corralled into the vague category of alternative singer-songwriters, but as a child raised on jazz and hip-hop, she entered the music business mostly unfamiliar with rock and roll. Producer Jon Brion brings some rock grooves and instrumentation to When the Pawn…, which lightens Apple’s compositions. Smoky guitar complements the piano in “The Way Things Are,” and “Limp,” a vengeful response to gaslighting, has the force of  a rock song. Single piano notes creep up in the verses and swishing sound effects add tension to Apple’s narrative of manipulation. The chorus is a double entendre of psychological and sexual abuse: 

No matter what I try you’ll beat me with your bitter lies

So call me crazy, hold me down, make me cry

Get off now, baby

It won’t be long till you’ll be lying limp in your own hands

In the years since 1999, critics have improved their writing about women and the nuances of their work. When the Pawn… is now perhaps Fiona Apple’s most beloved record, one she made by remaining steadfast in the face of criticism and, while expanding her style, remaining uniquely herself. Never again did she offer fans new music in a traditional time frame — this decade, she’s released only one album, 2012’s The Idler Wheel… (which has another long title). But as the 2010s close, it’s been on several “best of” lists. Each small appearance of the semi-reclusive artist now makes headlines as we anxiously await her next LP. 

In the aftermath of Tidal, When the Pawn… proved to be the first taste of Apple’s style — unabashedly quirky, but shapeshifting as well. Each succeeding album gave fans new pieces of herself to unravel. And it’s still making waves today: this year, singer-songwriter King Princess covered When the Pawn…’s devastating closing ballad “I Know,” and with Apple’s approval — she’s harmonizing in the background. 

Apple’s music holds up today, and she is finally treated with the respect she’s always deserved. But When the Pawn… remains a document of a less welcoming world. It’s a portrait of a young woman, dismissed for being young, blunt, wordy and beautiful, knowingly daring to keep expressing herself in the only way she knows how.

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