We have an accepted trajectory for pop stardom, no matter how loose. Even the odd overnight sensation is supposed to follow it: our stars start in obscurity, catch fire with a breakout single and then hold the public’s attention for as long as possible, making whatever compromises are necessary to safeguard their temporary seat at the table. There are plenty of exceptions, sure, but that’s usually how it goes.

Unless you’re Fiona Apple. More than just an exception, Apple downright inverts the formula, having moved from cool-as-fuck radio darling to reclusive eccentric. In 1996, when she was just 18, Apple released Tidal, which shifted nearly 3 million copies and featured the slinky smash-hit “Criminal.” Her youth skyrocketed her into the public eye, and she became the kind of widely-loved wunderkind that was suddenly speaking for an entire generation.

Quickly, Apple’s discomfort began to show, and, at the 1997 VMAs, she gave a now-famous acceptance speech where she decried MTV and called the music world “bullshit.” Her star went out almost on the spot, and she went on to make three more albums in comparative obscurity—improbably, she’d become a cult artist after an intense moment in the sun.

Each of Apple’s subsequent records are wonderful, but 2005’s Extraordinary Machine best exemplifies her status as an anti-pop heroine. First, there’s its troubled history: she recorded an entire version of the album with Jon Brion, it leaked and then she went back to the drawing board and reworked most of the record’s 13 tracks with Dr. Dre producer Mike Elizondo. More interesting, though, is the way that Extraordinary Machine twists musical tropes, both directly and indirectly commenting on the traditions of the pop singer-songwriter. The result is a vibrant, dizzying collection, full of forward-thinking sounds and arrangements that prop up Apple’s signature verbal acrobatics.

The title track, a lilting ode to self-love, is a hyper-literate response to generic pump-up anthems like Christina Aguilera’s “Beautiful” or Elton John’s “I’m Still Standing.” “Be kind to me, or treat me mean/ I’ll make the most of it, I’m an extraordinary machine,” Apple quips, building herself up without expressing the sort of rah-rah hyperbole that infects similar anthems. “I still only travel by foot, and by foot it’s a slow climb/ But I am good at being uncomfortable, so I can’t stop changing all the time,” she adds, maintaining a balanced approach by giving equal weight to her strengths and drawbacks. This self-aware streak gives the song a beating heart that’s missing from chilly self-empowerment fodder like La Roux’s “Bulletproof,” which elevates its subject to immortality instead of wrestling with their very real humanity.

Other songs tackle musical cliché even more directly. Like all of Apple’s records, Extraordinary Machine is a breakup album, and on “Please Please Please,” she points out the shortcomings of the form: “Please please please, no more melodies/ They lack impact, they’re petty/ They’ve been made up already,” she sings over prickly drums. There’s a whole song called “Not About Love,” where she stubbornly insists that she is “Not in love/ In fact [she] can’t stop falling out.” These canny, anxious moments perfectly spell out why Apple would’ve been a terrible pop star: she’s far too finnicky and jaded to write music that goes down smoothly. Her pop pushback can’t even be packaged as “rebellion,” in the Good Girl Gone Bad sense, because there’s nothing bratty about it—it’s just who she is.

Apple doesn’t have a glossy bone in her body, so she could never pull off the detailed-but-shiny balladry of Taylor Swift or the bratty-but-danceable musings of Marina and the Diamonds. Even Extraordinary Machine’s most straightforward moment, the swelling piano ballad “Parting Gift,” features bookish couplets like “I bet your fortressed face belied your fort of lace” and winks at itself by admitting that its villainous ex-lover was “always good for a rhyme.” The more you dig into Extraordinary Machine, the clearer it becomes that her cultural prominence was a fluke rather than a squandered opportunity—she belongs in the shadows, emerging every six or so years with fully-formed, neurotic mission statements that thrive on specificity.

The reason that Extraordinary Machine proves this more clearly than her sophomore record When the Pawn… or 2012’s The Idler Wheel… lies largely in Elizondo’s production. Aside from the fact that both of their titles are multi-stanza poems, neither When the Pawn… nor The Idler Wheel… sound even remotely poised for the radio. When the Pawn… features lurching, jazz-fusion concoctions and arty alt-rock singles, like latter-day Joni Mitchell met up with Alanis Morissette and they wanted to make something just for themselves. The Idler Wheel… often ignores musical conventions altogether, with porous, skeletal arrangements and grating industrial flourishes. Apple shrieks and quivers, alienating pretty much anyone who heard “Criminal” and thought of Sheryl Crow.

Extraordinary Machine, though, is produced by the man behind “I’m the Real Slim Shady” and P!nk’s “I Got Money Now.” Elizondo thrives on maximalism, always opting for walls of sound when mere fences will do. You can hear it in “Window,” a late Extraordinary Machine cut, by placing his version alongside the unreleased Jon Brion attempt. Brion’s soundscape is sparse, featuring a quiet guitar and some far-off plinks, while Elizondo’s is spacy and full of driving drums. Album highlight “Tymps (The Sick in the Head Song)” rides on a blaring boom-clap and xylophone melody. It should sound like a digestible pop song, but instead it opens with the line “Those boon times went bust.” No matter his instincts, they can’t supersede the idiosyncrasy of Fiona Apple. She may be an extraordinary machine, but she’s not a predictable one. And if her career had taken any path but the one it took, she probably would’ve broken down by now.

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