Post-Millennial Classics: Fiona Apple’s “O’ Sailor,” a Song that Shone Despite a Muddled Release Process

Extraordinary Machine, Fiona Apple’s third LP, suffered through a famously convoluted release, one that attracted a lot of attention to how it all shook down. Two decades later, what really stands out is the brilliance of the album’s material, with the stunning “O’ Sailor” deserving special mention among that hallowed bunch of songs.

What is the song about? And why could fans choose between two competing versions, neither one truly reflecting Apple’s actual vision for it? It’s a great story and an even greater song. So hoist the masts and prepare to embark on a journey into the nooks and crannies of “O’ Sailor.”

Welcome to the Machine

Fiona Apple had nothing left in the songwriting tank. Her first two soul-baring albums drained her of every topic she wanted to address. But at the start of 2002, three years after the release of her sophomore album When the Pawn…, her producer friend Jon Brion started bugging her to get rolling again. Apple, Brion, and a few others decamped to a Los Angeles mansion to start working on songs that Apple would build from scratch as she was making the record, a new process for her.

Apple struggled to find motivation to churn out the songs, however. When she did squeeze out a song, Brion would go to work on it. Unfortunately, Epic Records, Apple’s label, didn’t like the early results they heard at all, especially considering the money they were spending on preproduction. Despite some incredible material in the can, with many songs (including “O’ Sailor”) seemingly inspired by Apple’s breakup with Boogie Nights director Paul Thomas Anderson, both Epic and Apple agreed to shelve the record.

Leaked Tracks

That’s where things start to get really confusing. In summer 2004, some tracks from the project leaked on the internet. When fans heard these, they immediate started badgering Epic for the album’s release. The label was understandably leery considering the money it had already spent, but they agreed to fund more sessions on a lesser budget.

Meanwhile, Apple was convinced to give it another go, with the help of producers Mike Elizondo and Brian Kehew. Since the songs were all written, this process took only a matter of weeks. Yet there was still one more hiccup to endure: The leak of the entire album, as allegedly produced by Brion, on the internet.

Magazines and online music sites actually reviewed this bootleg, which made some wonder if Epic would even go through with the official release. They finally did in October 1985, meaning fans could compare and contrast the so-called “Brion version” of “O’ Sailor” with the official release. (The original take features more prominent drums and a slightly slower pace.)

Oh, and here are a few more things to make your head spin. Brion and Apple both denounced the leaked album as a fake of sorts that didn’t accurately represent what they were working on before the plug was pulled. It’s likely someone with access to the recordings clandestinely mixed them on their own and then leaked them. In addition, Brian Kehew claimed that the mix of the official release was also somewhat botched, because neither he nor Elizondo were available and Epic was up against a strict time limit to get it done.

The Meaning Behind “O’ Sailor”

For all that drama, whatever version of “O’ Sailor” you choose comes out sounding like a masterpiece. The odd piano figure that drives the song gives it the feel of a somewhat shaky boat trip. And Apple’s multifaceted lyrics winningly evoke the lingering disappointment at the end of a thwarted relationship.

Ambivalence reigns right from the start: I’m undecided about you again, Apple sings. There’s an honesty typical of her work that runs through the song, as she doesn’t simply lay all the blame on one side: It’s double-sided because I ruined it all. She acknowledges she seems to enter relationships that are doomed to fail at the start: Everything I have to look forward to / Has a pretty painful and very imposing before.

She admits this person came along at a time when she was vulnerable for someone to fill a void: One who set to get me wise and got me there and then, got me. But she doesn’t spare him her disdain for showing her the potential of it all, only to let it falter: O’ sailor, why’d you do it, what’d you do that for / Giving me eyes to view it as it goes by the boards.

In the end, we’re grateful we had the chance to hear Fiona Apple’s “O’ Sailor,” even if it was in two imperfectly rendered (according to the principals) versions. The song itself is pretty perfect all by itself, so we’ll call it a wash.

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Photo by Nathan Shanahan/WireImage