After writing her debut album, Tidal, when she was 17, Fiona Apple was painted as an ingenue – but she dispelled any impressions that she was an innocent just as fast as she emerged. As a classically trained pianist, her acerbic, sinewy songwriting nonetheless resists convention, pulling in off-kilter percussion and woodwind to explore the outer reaches of what might otherwise be reduced to “adult contemporary”. Her singular approach to rhythm and instrumentation sometimes verges on vaudeville. But she is best-loved for her lyrics (and her voice), betraying a self-knowledge – and sometimes a bitterness – beyond her years, and honesty sometimes to a fault. “When I have something to say, I’ll say it,” she has said. The unwieldy, 90-word title of When the Pawn … is infamous, but Apple’s second album is a perfectly-formed whole, running the gamut from rage to regret in just under 45 minutes. Produced by Jon Brion, with artwork and videos by Paul Thomas Anderson (Apple’s partner at the time), it featured Apple as sole songwriter on all 10 tracks, written following her fall from favour with the music industry. Two years earlier, she had accepted the prize for best new artist at the MTV Video Music awards with a controversial speech in which she expressed her ambivalence about celebrity and called “bullshit” on the entertainment industry as a whole. It came to define her, transforming her, in her words, from a “tragic waif ethereal victim” to a “brat bitch loose cannon”. With When the Pawn ..., she returned deliberately and defiantly, on her own terms. The lurching piano of opener On the Bound sets the tone, Apple breathing nimble smoke rings in the verse (“Hell don’t know my fury”) before erupting into flames with the chorus (“You’re all I need”). Through defiance (A Mistake, Limp) and desperation (To Your Love), she comes to something approaching acceptance with I Know, her voice bruised and beautiful over brushed drum and double bass. The three albums to check out next Tidal (1996) Apple was 19 when she released her debut album, after a demo tape wound up in the hands of producer Andrew Slater via his babysitter; it went on to go triple platinum. She is still best known by many for the first single, Criminal – and the controversy surrounding her state of undress in its video. Apple wrote it in less than an hour at Sony’s request for a hit. But opener Sleep to Dream – with its slumping, tumbling percussion and shimmery strings – better represents her singular style, somewhere between piano ballad and R&B, with unflinching lyrical honesty to the fore. In 2010, proud Apple fan Kanye West identified the line, “I have never been so insulted in all my life” as his favourite first line of any song (though it is not, in fact, the first line). The Idler Wheel … (2012) Apple met anticipation for her first new music in nearly a decade with her most stripped-back album yet: sparse and purposeful, with the electronic tilt to her past work notably absent. The Idler Wheel is almost a folk-country record, and finds the 34-year-old older, wiser and more ready to take responsibility for turbulence in her relationships than she had been in the past. “I could liken you to a shark the way you bit off my head / But then again, I was waving a bleeding old bone,” she admits on Werewolf, before concluding: “Nothing wrong when a song ends in a minor key.” Extraordinary Machine (2005) After long delays, Apple’s third album made its inauspicious debut unfinished on file-sharing sites; it was officially released months later and named album of the year by many outlets. Co-producer Brian Kehew has said Apple’s lack of clear vision was one factor in the hold-up (along with a micromanaging record label), and that comes across in the finished product. Extraordinary Machine is Apple’s most experimental record, as well as the most sonically rich – the opposite of what she would go on to achieve with The Idler Wheel seven years later. On Tymps (The Sick in the Head Song), every idiosyncrasy seems indulged, giving it the feel of a Disney soundtrack – or the Beatles at their most whimsical. One for the heads Across the Universe (1998) The most successful of Apple’s covers, of a stylish repertoire (mostly from live sets) taking in Sinatra and Hendrix, is her take on the Beatles’ Across the Universe, recorded for the Pleasantville soundtrack in 1998. Still her second-most-streamed track on Spotify behind Criminal, it is far from a deep cut, but her take on such a familiar (and – relatively for Apple – friendly) song foregrounds the molasses quality of her voice and her distinctive approach to instrumentation. The descending woodwinds after “nothing’s gonna change my world” are especially lovely. Further reading Fiona: the caged bird sings, by Chris Heath Chris Heath concluded his 1998 Rolling Stone profile, written in the thick of the fallout from the VMAs: “There is a long way to go in the Fiona Apple story.” Fiona Apple’s art of radical sensitivity, by Emily Nussbaum More than 20 years later, Emily Nussbaum picks up where Heath left off with her masterful profile of Apple at work in the New Yorker this month. Apple on grief Apple’s moving letter to fans about the death of her dog, Janet, over which she cancelled a tour of South America, has been removed from Facebook, but is immortalised alongside Apple’s lyrics on Genius. The primer playlist For Spotify users, listen below or click on the Spotify icon in the top right of the playlist; for Apple Music users, click here. • What are your favourite Fiona Apple tracks? Share them in the comments below. • Check out the rest of the Listener’s digest series here. 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