Song of the Day: Fiona Apple – “O’ Sailor”

Fiona Apple makes records when she wants to, not when she’s pushed into it by her record company. As a result, she has released only three studio albums in the last 14 years – 1996’s Tidal, 1999’s When the Pawn…, and 2005’s Extraordinary Machine (the troubled genesis of which is ripe for another blog at some point.) And she’s still only 32. But those three records are all some of the most singular singer-songwriter albums you’re likely to hear; unique and strange and inventive, Apple’s smoky, deep voice sings songs of love, loss, and regret within a template that takes in pop, jazz, and folk.

From Extraordinary Machine comes “O’ Sailor,” which as good an introduction as any to Apple’s style: thundering piano chords, evocative and imaginative wordplay, and that subtly passionate, graceful rich vocal delivery. Of course it would be nice for fans to have Fiona Apple albums in their hands with more regularity, but she always delivers the goods when she does, so what’s a little lateness between friends?


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