O’Sailor by Fiona Apple Lyrics Meaning – Navigating the Storms of Betrayal and Liberation


You can view the lyrics, alternate interprations and sheet music for Fiona Apple's O'Sailor at Lyrics.org.
Article Contents:
  1. Music Video
  2. Lyrics
  3. Song Meaning

Lyrics

I’m undecided about you again
Mightn’t be right that you’re not here
It’s double-sided ’cause I ruined it all
But also saved myself
By never believing you, Dear

Everything good I deem too good to be true
Everything else is just a bore
Everything I have to look forward to
Has a pretty painful and very imposing before

O’ sailor why’d you do it
What’d you do that for
Saying there’s nothing to it
And then lettin’ it go by the boards
O’ sailor why’d you do it
What’d you do that for
Saying there’s nothing to it
And then lettin’ it go by the boards

I have too been playing with fifty-two cards
Just cause I play so far from my vest
Whatever I’ve got, I’ve got no reason to guard
What could I do but spend my best

O’ sailor why’d you do it
What’d you do that for
Saying there’s nothing to it
And then lettin’ it go by the boards
O’ sailor why’d you do it
What’d you do that for
Saying there’s nothing to it
And then lettin’ it go by the boards

And after waiting, fighting patiently on my knees
All the other stuff tired itself out first, not me
And in its wake appeared the touch and call of a different breed
One who set to get me wise and got me there and then, got me

And what a thing to know what could be instead
Oh what a blessed curse to see
It took the agenda from its place in my bed
Made a merry paramour of me

O’ sailor why’d you do it
What’d you do that for
Saying there’s nothing to it
And then lettin’ it go by the boards
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

O’ sailor why’d you do it
What’d you do that for
Saying there’s nothing to it
And then lettin’ it go by the boards
O’ sailor why’d you do it
What’d you do that for
Saying there’s nothing to it
And then lettin’ it go by the boards

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
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

Full Lyrics

In the vast ocean of music that Fiona Apple has gifted to the world, ‘O’Sailor’ stands as a beacon of raw emotion and intricate storytelling. Through her hauntingly beautiful melodies and poignantly crafted lyrics, Apple embarks on a journey that grapples with notions of trust, disillusionment, and self-realization.

At a casual glance, ‘O’Sailor’ might seem like another lament of a forlorn love, yet, as we dive deeper beneath the surface, the sheer complexity and the emblematic nature of the song’s narrative begin to emerge. Apple epitomizes the artistry of encoding an elaborate personal saga within the lines of a ballad—a tale that resonates with anyone who has ever felt the sting of treachery or the emancipation that follows self-preservation.

The Dichotomy of Doubt and Conviction

Apple’s opening line, ‘I’m undecided about you again,’ immediately throws us into the tides of ambivalence that are central to this song. It captures a picture of someone torn between their emotional attachment and the recognition of something amiss—the notion that logic and intuition are at war. This struggle is not solely about the presence of another person but also reflects the internal conflict of trusting one’s own judgment.

The dichotomy continues as Apple confronts self-sabotage (‘I ruined it all’) but also acknowledges a form of salvation wrought from skepticism (‘But also saved myself’). Her instinctual disbelief protects her, hinting at the perennial human experience of self-defense in the face of potential heartbreak.

Expectation and Past Scars

Apple delves into the realm of expectations, poetically suggesting that anything perceived too good to be true can’t be trusted, ‘Everything good I deem too good to be true.’ This lyric underscores a sentiment of disillusionment fostered from past traumas, as Apple exposes the burdens of hope that often precede disappointment.

It’s her acquaintances with the ‘painful and very imposing before’ that casts a shadow over her prospects, a testament to the way previous suffering can tint the lenses through which we see our future. In this, Apple taps into a universal truth: the baggage of our history can heavily influence our tomorrow.

The Sailor Metaphor: A Tale of Abandonment

Apple turns to the allegory of a neglectful sailor, questioning the carelessness with which they treated her trust. This archetype can be interpreted in many ways—is the ‘sailor’ a lover, her own erratic emotions, or a more abstract concept of fate itself?

When she repeats, ‘O’ sailor why’d you do it, What’d you do that for,’ it’s as though she is interrogating the elusive force that led her to heartache. The ‘boards’ that things are let go by could be a reference to the wooden planks of a ship’s deck—an emblem of missed opportunities and discarded loyalty.

The Hidden Meaning: A Dual Journey of Vulnerability and Power

Fiona Apple allows herself to admit her vulnerabilities in this piece, candidly confessing to playing her hand openly in life’s game, ‘Just cause I play so far from my vest.’ But Apple’s admittance of vulnerability is not a defeat; rather, it’s an assertion of the power within transparency, an affirmation of strength in openness.

The song signals a transition from passive victimhood to an active embracement of wisdom, as Apple hints at an evolutionary phase in the line ‘One who set to get me wise and got me there and then, got me.’ Here, we witness the silent transformation from naivety to enlightened self-assurance.

Memorable Lines: The Curse of Seeing ‘What Could Be’

Among the song’s most striking lines is the oxymoronic ‘Oh what a blessed curse to see.’ It encapsulates the gift and the agony of insight—the ability to envision the potential beauty of what lies ahead, coupled with the awareness of the hurdles that impede its realization.

Fiona Apple’s graceful articulation of such a profound emotional condition is just one example of her lyrical finesse. ‘O’Sailor’ is laden with these powerful lines that resonate on multiple levels, beckoning listeners to partake in Apple’s journey towards self-recovery and autonomy.

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