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Fiona Apple’s 10 Best Songs

NASHVILLE, TN - SEPTEMBER 16: (L-R) Fiona Apple and Sean Watkins of the Watkins Family Hour perform at Mercy Lounge on September 16, 2015 in Nashville, Tennessee. (Photo by Erika Goldring/Getty Images for Americana Music)

Fiona Apple’s music isn’t pretty — it’s real. Though more folks appeared to have concentrated on her looks than her actual music, her 1996 debut, Tidal, continues to resonate with people all these years later in terms of how she channeling emotional depth in such a forceful and assured way. And she was just 18.

Now 42, Apple has an economical but essential catalog of music comprising four more challenging, confrontational and above all, classic albums, the latest, Fetch The Bolt Cutters, was released on April 17.

Upon its release, the album was almost entirely hailed by critics and fans alike. It had that kinda intensity where the hype almost turns you off a little. But there is no denying Bolt Cutters–a cumulative burst of everything brilliant about Apple as a producer, a musician, a singer and a songwriter. Flanked by a small supergroup of Soul Coughing bassist Sebastian Steinberg, fellow songwriter David Garza on guitar and Aimee Aileen Wood on drums and household objects, Apple and friends settled into her home alongside her beloved dogs Mercy, Maddie, Leo, Alfie and Little (all of whom have full artist credits in the liner notes) to create one of the best American pop records to be recorded inside an artist’s private residence, sharing company with the likes of Paul McCartney’s solo debut and The Hermit of Mink Hollow by Todd Rundgren.

Apple’s comparison is Joni Mitchell if Mitchell grew up in Manhattan during the Wu-Tang era, a composer who adds just enough Sondheim flair to sweeten the complex web of sound and emotion Apple presents; like a perfectly baked Italian biscotti. But any of the more theatrical sense of whimsy that informed healthy portions of both Extraordinary Machine and The Idler Wheel… is stripped down to the bone in such a way that renders her the sole living conduit connecting Bessie Smith and Billie Eilish. 

And while Bolt Cutters might ultimately be revered as the best Fiona Apple LP,  it’s important to measure its mettle against the albums that came before it. Choosing 10 individual Fiona Apple songs from this canon of five excellent full-lengths she’s created this past quarter-century was no easy task. But it sure was a satisfying journey through the music of a true American pop original.

“Not About Love” (2003 version)

For fans of Apple and Jon Brion, the anticipation over the singer’s long-delayed third album Extraordinary Machine was very high by 2005. Only what emerged was a wholly different recording than the record we expected, at least those of us who heard what it once sounded like. And though the more streamlined Machine produced by Mike Elizondo and Brian Kehew proved to be more than a fitting substitute, those of us who managed to score a copy of the leaked Brion mix will always favor the one that was scrubbed. The clear contrast between the two can be heard in its totality on “Not About Love,” which had originally been the opening cut to Extraordinary Machine before it was revamped and knocked down to the 11th track on the official release. But Brion’s pairing of cellos and Apple’s signature bounce on the piano proves those SMiLE comparisons to be ultimately true. Right down to the “lost classic ” status, even.


“Fetch The Bolt Cutters”

From Paul McCartney’s beloved sheepdog Martha to Bradley Nowell’s dalmatian to Freddie Mercury’s felines, musicians’ pets sometimes acquire a fanbase of their own. Yet the world wasn’t ready for Apple’s pack of sweeties, whose presence is quite prominent throughout Bolt Cutters. But not as much as the title track, (where the dogs are most utilized at the song’s coda), particularly her beloved pitbull Mercy. “Fetch The Bolt Cutters” also showcases the might of this homegrown band she assembled as well. 

“It smartly clocks her sometimes-perilous position as a role model for a younger generation of artists while directly referencing her own inspiration, with lyrics from Kate Bush’s ‘Running Up That Hill,” we said in our review of the album.”All of this bounces forward through a pot smoke haze with buoyant fretless bass by former Soul Coughing member Sebastian Steinberg. And it’s aided by Tchad Blake’s mix that gives it the feeling of being in a friend’s living room for an intimate late-night conversation.”


When “Criminal” was released as a single in September 1997, its drum-heavy, steady groove fit perfectly in an era dominated by such beat-driven acts as Portishead, Tricky and Bjork. But it was the swagger in Apple’s delivery, both at the piano and in her lyrics, that staying power as a force of nature in modern pop. And the way by which that formula of rhythmic cabaret had provided such an influence of artists heading into the 21st century remains as true as ever all these years later.

“Hot Knife”

Apple’s pedigree as a jazz singer is quite omnipresent in varying degrees across all of her work. But on The Idler Wheel’s “Hot Knife,” she goes full Ella. As she keeps time on tympanic and her sister Maude Taggart sings background vocals, the way by which Apple sings here is like scatting with actual lyrics instead of improvised vocalizations. In a recent profile on her in the New Yorker, Steinberg cites “Hot Knife” as the song that serves as the most telling breadcrumb from her earlier work that most closely resembles the direction of Bolt Cutters.

“Heavy Balloon”

Apple has been compared to Nina Simone quite often throughout these last 25 years. But it’s within this Bolt Cutters deep cut where she really seems to channel her spirit, both in the jazzy sway of her vocal delivery and her approach to the subject matter. The “Heavy Balloon” in this instance is depression. “The imagery of that one came to me years ago, because a boyfriend of mine was talking to me about his father and his depression,” Apple recently told Vulture. “The way he was describing his father moving around the house being weighed down by something made me think, We’re just always trying to keep it up; oh my God, this is not staying off me long enough, I just can’t really move around. It’s this hindrance, this obligation, this constant thing to be taken care of.”