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Fiona Apple Has Never Made a Bad Album. But Which Is Her Best?

Apple’s catalog is a breadcrumb trail leading the intrepid listener to startling revelations about love and self-sufficiency. Photo: Kitra Cahana/Getty Images

I should start by saying that in nearly 25 years of listening to Fiona Apple, I’ve never heard a bad album and have scarcely encountered a bad song. The list below is a list of Fiona albums ordered by degrees of greatness. It’s a story of an artist whose music has grown somehow a little more pure each step of the way, whose catalog is a breadcrumb trail leading the intrepid listener to startling revelations about love and self-sufficiency. Back in 1996, when I was using Tidal lyrics to stoke the fires of doomed crushes on classmates, Fiona’s music was a light at the end of the tunnel of high school. Here was someone who understood the intensity of teenage feelings but who had gained the necessary distance to view them as sort of silly. It took time to see, say, “Carrion” — “My feel for you, boy, is decaying right in front of me, like the carrion of a murdered prey” — as a piece of deliberate melodrama. I’m still learning to be as chill about strife as “Extraordinary Machine” plays at, to see the quest to be “cool” as the act of futility and wasted time “Fetch the Bolt Cutters” is telling me it was all along. As she grows, we grow.

5. Extraordinary Machine (2005)

The three-year journey to the release of 2005’s Extraordinary Machine was an obstacle course for Apple and her friend and collaborator Jon Brion, also known for his work with Macy Gray, Aimee Mann, Kanye West, and Mac Miller, as well as the soundtracks to films like Eternal Sunshine of the Spotless Mind, I Heart Huckabees, and Punch Drunk Love. The pair began work on a follow-up to 1999’s When the Pawn … in the early 2000s, matching Apple’s sharpening lyricism and classical pop melodicism with Brion’s playful orchestral underpinnings. A trickle of promising leaks whetted fans’ appetites, but radio silence from the label about a release date led to wide speculation that the third Fiona album had been shelved. This, in turn, led to petitions, protests in front of Sony’s Manhattan offices, and a riotous campaign to mailboxes of apples marked with the names of angry fans to the heads at Epic thought to be holding new music up. Extraordinary Machine secured a date but not before the Brion cut slipped out on peer-to-peer services.

The version of Extraordinary Machine released to retailers in October 2005, reworked in large part by hip-hop producer Mike Elizondo (who played on a few cuts on When the Pawn …) along with engineer and sometime electronic artist Brian Kehew, is full of upbeat tunes that suppose the artist who made Tidal’s “Criminal” had intended to see that song’s commercial interests all the way through. That makes for intriguing tunes like “Tymps (The Sick in the Head Song),” a thumper that could only have come from a producer who made records with Dr. Dre, but also solid songs like “Window,” “Get Him Back,” and “Better Version of Me,” rendered somewhat cloying by the cutesy arrangements. Less is more on Machine. The highlights are bare-bones numbers like “Parting Gift,” “O’ Sailor,” and “Oh Well.” (Fittingly, the first two were singles.) Still, the title track and opener, left untouched from the Brion sessions, looms over the reminder of the thing as a vision of the eccentric greatness this still-quite-good album narrowly missed.

4. Tidal (1996)

Fiona Apple’s 1996 debut album is a peculiar document of the mid-’90s singer-songwriter wave. The syncopated hip-hop drums guiding the singles “Sleep to Dream” and “Criminal” plant Tidal in the same connected universe as Tori Amos’s “Caught a Light Sneeze,” Sarah McLachlan’s “Sweet Surrender,” and the year where the success of McLachlan’s Lilith Fair put a spotlight on the creativity and buying power of women in music. At 19, Apple was the youngest artist to grace the Lilith main stage, but dive into her record and the singer seemed wise beyond her years, more a follower of jazz powerhouses like Sarah Vaughan than a newcomer rising up in McLachlan’s court. Tidal’s big hits were clever pump fakes, luring listeners in with modern production flourishes, ensnaring them with sticky, big-band deep cuts, and then dissolving their calm with Apple’s withering words.

The pen was devastating. “Sullen Girl” recounts a sexual assault and its fallout in mythic terms: “They don’t know I used to sail the deep and tranquil seas / But he washed me ashore, and he took my pearl / And left an empty shell of me.” “Pale September” describes a lover the way a wildlife documentary tracks subtle movement in a pond: “He goes along just as a waterlily / Gentle on the surface of his thoughts, his body floats / Unweighted down by passion or intensity / Yet unaware of the depth upon which he coasts.” Tidal is dense and beautiful, if a touch heavy-handed, a great album portending greater ones yet to come.

3. The Idler Wheel (2012)

Exhausted by the protracted delays and reworks Extraordinary Machine suffered, Fiona worked on new music in fits and starts when touring ended but neglected to inform Epic until 2012, when she turned a finished album in by surprise. Produced by Apple herself (with help from the Divinyls’ Charley Drayton, her touring drummer), The Idler Wheel peels the layers off her songs, leaving nothing behind but raw vocals, accomplished piano playing, driving percussion, light embellishments including splashes of guitar and other chordophones like koras and bouzoukis played by Drayton and unobtrusive bass notes from former ex-Soul Coughing player Sebastian Steinberg. Unweighted by elaborate arrangements, these songs emote not on tone-setting mise-en-scène but through the power of Apple’s words and delivery. “Regret” details a breakup in brutal biological terms: “I ran out of white dove feathers / To soak up the hot piss that comes from your mouth every time you address me.” “Left Alone” encapsulates the rise and fall of a doomed couple in the ostentatious melodies and bookish phraseology of a show tune: “You made your major overtures when you were a sure and orotund mutt / And I was still a dewy petal rather than a moribund slut.” “Hot Knife” draws a straight line through vaudeville, blues, and tribal chants, portraying Fiona Apple as both musician and musicologist while setting the stage for her next album’s breakthrough.

2. Fetch the Bolt Cutters (2020)

The Idler Wheel seemed a daring new direction in 2012, but her next album proved Apple might not be done pivoting. The last album limited itself to just the sounds necessary to advance the message of the song. The new one wonders why — if it doesn’t need to be elaborately produced — there needs to be an outside studio at all. Fetch the Bolt Cutters unites the singer and longtime players Steinberg and David Garza, the guitarist she picked up as an opener on the Extraordinary Machine tour, inside Apple’s home. Bolt Cutters sports a more robust sound than Idler without cluttering the mix with unnecessary noise. It actually feels homemade, thanks in part to the tools on hand: Friends, animals, and household items get repurposed as makeshift melodic and percussive instruments. One song credits Apple playing a chair and Steinberg tapping a lighter on a Wurlitzer; another credits the singer’s dog Mercy for thrashing around in the background. The symphony of barking dogs that arises the climax of the title track is a happy accident resulting from friends Cara Delevingne and Zelda Hallman bringing pets over.

Fetch the Bolt Cutters centers Fiona’s musicianship and her quest for inner peace. This music dispenses wisdom earned through decades of peaks and valleys, of romances coming and going and of windfalls and crashes in the business of making music She’s come out with an album celebrating women. The title track laments time wasted trying to fit in as a young artist; “Shameika” remembers a time a girl in school told her she was better than the people she so badly wanted to impress. “Newspaper” and “Ladies” detail the ways that dating men unnecessarily complicates relationships between women. “Cosmonauts” muses about growing old with a man on the condition that he keeps his act together. But Bolt Cutters isn’t all roses. “Heavy Balloon” is a chilling metaphor for depression, and “For Her” speaks up for a friend victimized by a male benefactor. “Under the Table” parlays a story about an argument at a dinner party into an admission of what fans of Fiona Apple have known all along: “Kick me under the table all you want / I won’t shut up.”

1. When the Pawn … (1999)

Two years after being played off as crazy in the wake of VMA-gate, Fiona issued a warning in the opening verse of her sophomore album, When the Pawn …: “Hell don’t know my fury.” With Tidal utility player Jon Brion onboard as producer, Apple pushed out past the artful cabaret of her debut album into a wider array of sounds and sensibilities. Pawn pours fuel on the fire Tidal flashed in “Sleep to Dream.” “On the Bound” is a tour de force, pairing naked emotion, raw intensity, and hip-hop cadences, all of this in the middle of a storm of sweeping orchestral accompaniment. “The Way Things Are” and “A Mistake” add punchy rock songs to the repertoire. “I Know” and “Paper Bag” prove Apple’s knack for timeless piano ballads was no beginner’s luck.

If, in songs like “Shadowboxer” and “Sleep to Dream,” Tidal portrayed Fiona Apple as a passive, wide-eyed narrator — the Nick Carraway of her stories in the sense that she was someone things happened to rather than the person making the things happen — When the Pawn … is her awakening as a vengeful protagonist. “Limp” cleverly puts a lying significant other on notice: “It won’t be long till you’ll be lying limp in your own hands.” “Get Gone” follows through: “Put away that meat you’re selling.” “Love Ridden” is the scintillating goodbye, as Apple weans herself off pet names for an ex mid-sentence: “I want your warm, but it will only make me colder when it’s over / So I can’t tonight, baby / No, not ‘baby’ anymore / If I need you, I’ll just use your simple name / Only kisses on the cheek from now on / And in a little while, we’ll only have to wave.” The daunting honesty, cunning poetry, and confident musicianship When the Pawn … displays make for a work that isn’t only Fiona Apple’s best but one of the finest musical offerings of its decade overall.

What Is Fiona Apple’s Best Album?