The 15 Best Fiona Apple Songs

Music Lists Fiona Apple
Share Tweet Submit Pin
The 15 Best Fiona Apple Songs

Earlier this week, Fiona Apple let loose some much pined-for information regarding her eagerly awaited new album, via an extensive interview with The New Yorker. The new record (with a still unannounced release date) is called Fetch the Bolt Cutters, taken from a Gillian Anderson quote. “Really, what it’s about is not being afraid to speak,” Apple said in the profile. As it turns out, Apple has never been afraid to speak throughout her 25-year career. She has repeatedly divulged and desecrated the rumors and gossip surrounding her public persona, but instead of doing so in the press, she usually prefers to address those matters in her music (except for the occasional, incredible public outburst, like her famed acceptance speech at the 1997 MTV Video Music Awards, or, more recently, her spur-of-the-moment interview with Vulture). But take away all the noise, all the speculations about what she’s up to and when she’ll release something next, and Fiona Apple is still one of the most innovative artists to have walked the earth in the last three decades. She has released four near-perfect albums, and she continually pushes the boundaries of what it means to be a pop artist. These days, the 42-year-old rarely leaves her house in Venice Beach, Calif., but for those of us in the outside world, her music remains a sort of salve to the chaos that has unfolded since the most noteworthy moments of her career. In anticipation of the new music and celebration of what she has already accomplished, we took a look back at some of Fiona’s best songs. Here are 15 of our favorites.

15. “Please Please Please”

Extraordinary Machine consists of some of the more subtle Fiona Apple songs—if there even is such a thing as a “subtle” Fiona Apple song. But “Please Please Please,” falling at number nine in the tracklisting on the 2005 release, is just what it sounds like: a plea, and a pretty non-straightforward one at that. It’s a kind of whirling, all-encompassing prayer, one that feels eerily timely right now in this age of separation and isolation. “Please please please / No more maladies / I’m so tired of crying / You’d think I was a siren,” Apple sings. Sound familiar? While this delightful song probably had something to do with Apple’s public image and her struggles surrounding it, now it just sounds like a coronavirus anthem: “Give us something familiar, something similar,” she goes on to sing. “To what we know already / That will keep us steady.” She had to be referring to binging sitcoms on Netflix during a pandemic, right? Obviously not, but it feels pretty dang clairvoyant. —Ellen Johnson

14. “Extraordinary Machine”

Just when you think you know what to expect from a Fiona Apple song, she goes and sounds off a church bell. The opening title track from Apple’s third album Extraordinary Machine sounds like both a deleted Norah Jones demo and a slapstick solo that might occur at the first half of Act II in a Broadway show (featuring most of the orchestra’s woodwinds, too). This album arrived after a long six-year intermission since 1999’s When The Pawn…, and as if to tease us for our impatience, Apple fills us in on what she was doing in the meantime right away: “I certainly haven’t been shopping for any new shows / And I certainly haven’t been spreading myself around,” she sings. As it turns out, these informational verses were only a harbinger of long waiting periods between albums to come. Fiona Apple mostly remains an unhurried recluse, but at least the wait’s always worth it. —Ellen Johnson

13. “Periphery”

The Idler Wheel…, Fiona Apple’s most recent album released in 2012, is full of strange and spooky soundscapes. The kooky vamping on “Periphery” may just be my favorite. Apple’s dedicated anthem to the fringes is a rare moment of lightheartedness on the record (or in any of her records, for that matter) and features shredding percussion and bouncing piano, but it’s still a biting shutdown in the end. “You let me down / I don’t even like you anymore at all,” Apple sings at one point. Even when she’s being silly, Fiona’s always working an ulterior motive. —Ellen Johnson

12. “Never Is A Promise”

The conflict of Fiona’s music often oscillates between what she wants and what she thinks is possible. “Never Is A Promise” finds safety in fatalism. At just 19, Fiona understands what she thinks to be her place, the order she can’t upset lest she never finds peace again (“I realize now what I am now too smart to mention to you”). Fiona’s writing can take a sinister turn at the drop of a hat, though—the girlishness of her pianos and violin can sour, adopting vicious grit in their too-loud, too-forceful delivery. Even when lost in a whorl of depression, Fiona is sober enough to point out the empty promises of empathy assured by lovers, family, strangers. It’s what makes her music eternally relatable; she’s unafraid to appear resentful for us, and live on in righteous spite. —Austin Jones

11. “Sullen Girl”

This song’s title gives its mood away even before the somber keys do. It’s a downer, to be sure, but it doesn’t feel like useless spiraling. This is a productive sadness. Apple takes a few moments on her debut album to sulk and stare aimlessly ahead, having herself a metaphorical cleansing cry and a bout of self-pity before picking things back up again on the very next song, “Shadowboxer.” She says it best: “It’s calm under the waves / in the blue of my oblivion.” Sometimes a moody hiatus is just enough to get you feeling back to normal. —Ellen Johnson

10. “Every Single Night”

The Idler Wheel… was Fiona’s third big comeback, and until the recent announcement of Fetch the Bolt Cutters, the longest period between her studio releases. Even after seven years, she still had it, releasing what is arguably her best album since Tidal. “Every Single Night,” the album’s sole single, twinkles with a childish fear, heralded by the equally delicate timbres of her frequently used marimba and a less used celesta, which is perhaps most recognizable on “Dance of the Sugarplum Fairies.” Fiona’s description of her anxiety manifesting is detailed with razor-sharp precision (“These ideas of mine / Percolate the mind / Trickle down the spine / Swarm the belly, swelling to a blaze”), in direct juxtaposition against her heroic struggle against depression’s stagnancy. If Fiona’s music could be described by its characterization, she’d be a brave soul responding to her own cowardice. Her strength, in response to her knee-buckling fear, is laid bare by a central tenet, a refrain that could very well summarize her work up until this point: “I just wanna feel everything.” —Austin Jones

9. “The First Taste”

There’s something so sensual about the consummation of a first kiss. For Fiona, it’s primal, an evolutionary truth marked by dominance and consumption. In a wonderland of keys, a dizzyingly repetitive piano chord competes with vibraphone, somehow growling with unexpected violence, and, for a moment, it feels so damn comforting to be caught in the rituals of first contact, as bestial and scary as they can be. It’s what Fiona excels at—a vulnerable reconstruction of patterns we all notice in ourselves. “The First Taste” is shocking even 20 years later in its brutal, fragile, undisguised perspective on sexuality. Fiona, as usual, is nervous but willing to burst our placid fantasies and expose them for what they are: a continual role play of a dangerous game. —Austin Jones

8. “Paper Bag”

Katy Perry could never. Before there was ever a whimper of “Do you ever feel like a plastic bag?” Fiona Apple was singing this sweet and sultry song about a fleeting glimmer of papery hope. She sings the melody with a sly, Regina Spektor-ish curve—almost like a dark bar piano tune. But this is no cabaret solo. “Paper Bag” is, plainly, about one woman’s isolation in the wake of desolated relationship, one that crumbled because he was a weak “little boy” and she was “a mess he don’t wanna clean up.” But she hungers for him anyways, and the endless cycle of craving, satisfying, starving repeats itself once more. —Ellen Johnson

7. “Werewolf”

Maybe it’s just me, but “I could liken you to a werewolf” is Fiona’s cleverest use of wordplay to date. “Werewolf” is defiant all the way down, from Fiona’s subtle gestures to her own hand in her relationship’s failure (if he’s a werewolf, she’s a full moon: instigating, yet passive) to this plea, which seems like a convenient deflection: “Nothing wrong when a song ends in a minor key.” To prove her point, she does just that. Catharsis doesn’t have to end happily. Discordance can be just as satisfying, depending on the type of comfort you’re looking for. —Austin Jones

6. “Limp”

Many songs throughout Fiona Apple’s discography could be described as hungry for something: sex, love, isolation, escape, revenge. The sonically busy, thematically cocksure “Limp” is perhaps most hungry for the truth. This unmistakable tale of a parter who can’t quit the gas-lighting game is consistently angry—and rightfully so. This “man” who Apple warns of throughout the song may have spent a considerable amount of time emotionally torturing her, but, before long, she’ll up and leave him with nothing but his own hand for pleasure: “It won’t be long till you’ll be lying limp in your own hands,” she spits with a vengeance. No one does rage and underhanded revenge with quite as much finesse as Fiona. —Ellen Johnson

6. “Criminal”

From the first few majestically unhinged notes to the devilish alto chorus of Fiona Apple’s biggest hit, “Criminal” is as masterful as anything in her discography—and she recorded it when she was just 19. The song recently made a buzzy and beautiful resurgence when Jennifer Lopez impeccably pole danced to it in the 2019 film Hustlers, but we didn’t need an immaculate strip-tease routine to remind us this song is just dripping in sexuality (but it is, truly, one of the most memorable moments in the movie, or any movie that came out last year, for that matter!). The first two lines in the song are “I’ve been a bad, bad girl / I’ve been careless with a delicate man,” and while we don’t condone sex as a means of power manipulation, we do condone Fiona Apple clowning on any lousy guy she pleases. Ultimately, this song is about sex and love and good and bad and guilt and responsibility, but it could be about anything and we’d still listen to that honeyed-barrel-of-a-voice that Apple possesses and first wields remarkably well here. —Ellen Johnson

4. “Hot Knife”

Whew! Is it getting hot in here? Undoubtedly one of the most intensely sexual and purely thirsty songs in Fiona Apple’s catalogue (and that’s saying something), “Hot Knife” is a miraculously strange and uniquely specific rendering of sexual tension. The constant pit-patting of the booming timpani drum acts like a metronome as Apple repeats, with increasingly frantic energy, that same oily verse over and over: “If I’m butter, then he’s a hot knife.” Apple’s sister Maude eventually joins in with backing vocals, and they begin to sing in the round. Apple says what’s on her mind loud and clear over tip-toeing keys: “He excites me / Must be like the Genesis of Rhythm / I get feisty / Whenever I’m with him,” she sings. This Idler Wheel… highlight remains one of the most memorable songs Apple has ever created. —Ellen Johnson

3. “Shadowboxer”

With a rumbling piano-based start featuring Apple’s distinctive timbre, “Shadowboxer” moves along a soulful jazz rift as it describes the disorientation of a complicated relationship. There is naturally a lot of angst here, building alongside strings that enter hesitantly as the vocals turn accusatory. But like many of Apple’s best songs, all of this breaks through to a cathartic chorus, relaxing somewhat with the defiant and weary admission, “I’m a shadowboxer baby / I wanna be ready for what you do / And I’ve been swinging around me / ‘cause I don’t know when you’re gonna make your move.” You can feel the exasperation, especially when she leans into an emphasis on the vowels in “swinging” and “around,” which leaves a dizzying impression. “Shadowboxer” is a showcase of Apple’s vocal and emotional range, and a prime example of why her songs continue to resonate. —Allison Keene

2. “Sleep to Dream”

You have to be careful with “Sleep to Dream,” because it unlocks unparalleled female energy. Rhythmic vocals act like an incantation over an aggressive drumbeat, which Apple punctuates with: “You say love is a hell you cannot bear, well then give me mine back and then go there, for all I care.” If you haven’t yelled those lyrics, you should give it a go. The chorus doesn’t let up the sentiment, though a string accompaniment does help put Apple (and us) in a triumphant posture above the righteous anger: “Don’t forget what I told you, don’t come around, I’ve got my own hell to raise.” The verse then goes right back into that tumbling, insistent, almost spoken-word declaration of brilliantly-crafted hard truths about someone you have been long ready to excise from your life. Do so! And then exalt, middle fingers in the air: “Just go back to the rock from under which you came, take the sorrow you gave and all the stakes you claimed … and don’t forget the blame!” —Allison Keene

1. “Fast As You Can”

Those DRUMS. Those KEYS. The intensity of this song’s intro paired with a series of fast-talkin’ warnings gives “Fast As You Can” its overall feeling of urgency, something Fiona Apple has excelled at from Tidal’s rumbling lead-off track “Sleep to Dream” all the way to the see-sawing “Periphery” on The Idler Wheel…. Released somewhere in the middle of Apple’s high-profile relationship with Paul Thomas Anderson, this song immediately fell victim to hearsay. It’s hard to listen to the song today without thinking about the Apple/PTA junction, a fiery partnership between two creators who never figured out how to tame the wild love that’s so acutely described in When The Pawn…. The song is a perfect snapshot of those feelings, as well as a rousing anthem for anyone who’s ever felt tired and trapped in a relationship. Remove the gossip and noise from the equation, and it’s just a timeless banger—the best one Fiona Apple has ever released (so far). —Ellen Johnson

Also in Music