Fiona Apple's Albums, Ranked: Critics’ Picks

Every Fiona Apple album offers something a little bit different: her approach to songwriting and production has consistently evolved, finding new prisms in which to refract her inherent genius.

Over the course of a quarter-century career, Apple has transcended the one-hit wonder status that was conveniently bestowed upon her by ‘90s alt-rock listeners, upended expectations for what a pop record could sound like, made fans wait years and then rewarded their patience every time. With fifth album Fetch the Bolt Cutters wowing listeners during a difficult period around the globe, Apple has returned at a moment when her brilliance is particularly needed, and once again caused arguments as to which of her albums is now her most vital.

All five of Fiona Apple’s albums are must-listens, make no mistake. Yet here’s how her sterling discography shakes out in our humble opinions, with a spectacular new entry to slot into place:

5. Tidal (1996)

Fiona Apple was only 18 years old when she released her debut studio album, Tidal; she and her piano fit as well in a low-lit, smoky club as they did on MTV, which played the controversial fallen-angel music video for the Grammy-winning “Criminal” to the point of exhaustion. Apple was not the only angsty female solo artist in radio rotation at the time, but she was too singular to simply be part of a trend: Her music was composed of floating jazz and brooding poetry, formats that were flexible enough to allow her to experiment and wander, as she worked through tough topics like her own sexual trauma. “And he took my pearl / And left an empty shell of me,” she sings on “Sullen Girl.”

Tidal was sorrowful, but it also had teeth — on closer “Carrion,” she compares her dying interest in a man to “the carrion of a murdered prey.” Is there a more effective way to convey your disgust than to liken someone’s appeal to decaying animal flesh? – CHRISTINE WERTHMAN

4. Extraordinary Machine (2005)

When The Pawn… producer Jon Brion reunited with Fiona Apple around 2002 for what would become version one of Extraordinary Machine, but after that rendition was shelved, a bootleg leaked online; the official album came years later, courtesy of producers Mike Elizondo and Brian Kehew. While some prefer Brion’s more cinematic rendition and others like the eclectic ride of the latter sessions, both succeed because they have the backbone of Apple’s songs holding them up.

Apple was lighter on Machine, employing a stylistic hodgepodge ranging from vaudeville on the title track to hip-hop on “Tymps (The Sick in the Head Song).” Personal relationships, particularly failed ones, still provided ample fodder for the reflective, glum but not always regretful, lyrics. “The sign said stop/ But we went on wholehearted/ It ended bad, but I love what we started,” she sings on “Parting Gift.” Amid the playfulness and wistful recollections, there was also fury. Between breaking windows on “Window,” threatening to “kill what I cannot catch” on “Get Him Back” and shouting about “wasted unconditional love” on “Oh Well,” Apple reminded anyone within earshot that she was not to be trifled with. – C.W.

3. Fetch the Bolt Cutters (2020)

In the eight-year gap between Fetch the Bolt Cutters and its 2012 predecessor, the music industry has been taken over by streaming. Buying full-lengths has largely become a thing of the past, playlist placement is more critical to success, and as such, a good chunk of popular music designed to continue a vibe rather than disrupt the flow. Part of the appeal of Fetch the Bolt Cutters is that it thrashes against such a languid approach to creative output, and instead has arrived as a bold, cacophonous ball of beautifully expressed thoughts.

Dogs bark, pots bang, pianos are hammered and syllables are elongated to an absurd degree; Apple prods at the unhealthy expectations of a patriarchal society, and zero apologies are offered — “I would beg to disagree, but begging disagrees with me,” she asserts. Fetch the Bolt Cutters is a fever dream that refuses to let go of its listener’s attention, and while it will be interesting to see how its elliptical songs hold up in the coming months and years, one gets the sense that its unyielding urgency will never fade. – JASON LIPSHUTZ

2. The Idler Wheel… (2012)

Apple evolves so much with each new album that it’s hard to pick one that’s most representative of her appeal, but her fourth album may be the most complete showcase of her talents, effortlessly balancing unadulterated emotion, immaculate lyrical construction, pop craft and inventive production choices like spinning plates across its track list.

As the only album that Apple released in her thirties, The Idler Wheel… is marked by a restlessness — quite literally, on the searing opener “Every Single Night” — but also a sense of newfound wisdom, as Apple looks back on romantic endeavors and examples of personal exploration with more restrained arrangements than ever before, jazz influences seeping into the cracks, her voice unadorned and each new line more impactful than the one before it. There are songs on The Idler Wheel…, from “Hot Knife” to “Werewolf” to “Jonathan,” that are among the very best of Apple’s career, yet the album begs to be consumed whole, a dizzying display of talent that also sounds righteously human. — J.L.

1. When the Pawn… (1999)

Three years passed between Fiona Apple’s 1996 debut and her follow-up with the 90-word title, shortened to When the Pawn…, and by the time of that sophomore album, Apple was lightyears ahead. The 1999 LP, produced by Jon Brion, revealed a greater emotional depth and specificity to her lyrics, a gruffness in her voice and an experimental side with her rhythms. Her piano became a percussive force on opener “On the Bound,” and she played with tempo on lead single “Fast as You Can,” switching from frantic to slinky and back again. She remained a self-proclaimed mess: “But I sure had fun,” she sang on the spacey “A Mistake.”

She was also funny and conversational in her reflections, recounting dialogue between herself and a lover on the jaunty “Paper Bag”: “He said, ‘It’s all in your head’/ And I said, ‘So’s everything’/ But he didn’t get it/ I thought he was a man/ But he was just a little boy.” Apple didn’t look to men as saviors, and she certainly didn’t want them looking at her that way either: “Baby, I can’t help you out / While she is still around,” she sang as the other woman on “I Know.” King Princess’ cover of the song with Apple in 2019 remained true to the original, showing the enduring perfection of Apple’s version.

The same is true for the entirety of When the Pawn…, the album that showed listeners not only who Apple was but what she would become: forever an artist on her own page, sullen and self-aware but with dukes up and a wicked grin beneath her doleful eyes. — C.W.