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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)

“To Your Love”

Upon the album’s recent 20th anniversary, there’s been a story being passed around in the press about how Fiona Apple read the reader mail published in the issue of SPIN following the Terry Richardson-shot cover story, which inspired the 90-word freeform poem she used to title her second LP. But she also took that negative energy and turned it into such driving material as the forceful “To Your Love,” where she dives into Morphine territory with its dark jazz shuffle that billows into a steelier version of the young woman who wrote “Sleep To Dream” in 1995. 

“Carrion”

Brion may not have produced Tidal, but as a multi-instrumentalist, he is all over these songs. But the former Til Tuesday guitarist reached his creative apex on the album’s closing number, bringing the orchestral sweep home with a positively Harrison-esque solo that foreshadows the electric pop he’d be making with Aimee Mann three years later for the soundtrack to Magnolia, directed by Apple’s one-time beau Paul Thomas Anderson.

“Paper Bag”

Perhaps no other song in the Fiona Apple songbook is as “Fiona Apple” as this second single from Pawn, which for a select few remains her singular masterpiece. Like when Randy Newman penned “Political Science”, it’s a tune that exposes the signature sound she has created in its purest form. It’s also one of her most forthcoming songs lyrically in how it addresses how one handles a lover’s mental health when she sings: “And I want him so bad, oh it kills / ‘Cause I know I’m a mess he don’t wanna clean up.”

“O’ Sailor” 

“O Sailor” was the first song from the revised edition of Extraordinary Machine when it was released via Apple’s MySpace page following the announcement of the album’s street date. It’s arguably the most cohesive collaboration between Elizondo and Apple on the record, especially in the push-pull of the singer’s seethe and the producer’s menacing rhythm and how they weave together in their interplay. But in terms of “O’ Sailor,” it’s the official version that is the superior version.

“Every Single Night” 

The first single off The Idler Wheel was an opening declaration of independence in regards to how in control she was with her music. In fact, she turned in a finished album without the knowledge of Epic Records that she was even working on the follow-up to Extraordinary Machine in the first place (lesson learned, it seems). And in kind, she and co-producer Charley Drayton (Keith Richards, Roseanne Cash)–utilizing nothing more than a celesta, a marimba and the strength of Apple’s voice–turned in a slow build of tune.