The single's video, directed by Floria Sigismondi, was filmed aboard the RMS Queen Mary and premiered on VH1 on November 7, 2005. It was nominated for eight Music Video Production Company Awards — in the categories of "Direction of a Female Artist", "Director of the Year", "Art Direction", "Cinematography", "Choreography", "Styling", "Hair" and "Make-Up" — and won two: "Direction of a Female Artist" and "Hair".
Oh Sailor
Fiona Apple Lyrics
Jump to: Overall Meaning ↴ Line by Line Meaning ↴
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
O' Sailor, why'd you do it
What'd you do that for
Saying there's nothing to it
And then letting 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 letting 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 letting 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 letting 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 letting 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
The lyrics of Fiona Apple's song "Oh Sailor" are centered around a sense of indecision and regret that the singer expresses about a past relationship. In the first verse, she's uncertain whether it was right for the person not to be with her, and she's acknowledging responsibility for ruining the relationship while also acknowledging that she "saved herself" by not entirely trusting the other person.
The second verse seems to reflect a broader pessimism about life, with the singer saying that everything good seems too good to be true, and everything else is boring. She doesn't have anything to look forward to because there's always some kind of difficult obstacle standing in her way.
The chorus repeats twice throughout the song, with the singer asking why the sailor did what they did in ending the relationship, and expressing a sense of frustration that they said there was "nothing to it" but then let it go. The lyrics seem to be directed at someone who's not taking responsibility for their actions and isn't even acknowledging the extent of the situation.
In the final verse, the singer reflects on the aftermath of the relationship, saying that she "played with fifty-two cards" (i.e. played fair), despite the fact that the other person did not. She mentions that she's been patient and has finally found someone who makes her feel appreciated, but acknowledges the bittersweet nature of realizing what could have been. The final repetition of the chorus suggests that she's still frustrated by how the sailor handled the situation, but she's also moved on and sees the relationship as something that's passed her by.
Overall, Fiona Apple's "Oh Sailor" is a complex exploration of regret, responsibility, and the difficult process of moving on from a past relationship.
Line by Line Meaning
I'm undecided about you again
I am unsure about my feelings for you.
Mightn't be right that you're not here
It doesn't feel right that you are not here with me.
It's double-sided, cause I ruined it all
I accept responsibility for ruining our relationship.
- But also saved myself, by never believing you, Dear
I made the intentional decision to not believe in you, which ultimately saved me.
Everything good, I deem too good to be true
I struggle with believing that good things can happen to me.
Everything else is just a bore
Other than good things happening to me, everything else is uninteresting.
Everything I have to look forward to
My future prospects
Has a pretty painful and very imposing before
Although my future prospects seem good, there are still difficult challenges and obstacles ahead.
I have too been playing with fifty-two cards
I have played this game strategically and cautiously.
- Just cause I play so far from my vest
I keep my true motives hidden, probably because I'm not fully trusting.
Whatever I've got, I've got no reason to guard
I have nothing to hide because I'm being honest.
What could I do, but spend my best
I put forth my best effort even though it may not be enough.
And after waiting, fighting patiently on my knees
I have waited and fought tirelessly for this.
All the other stuff tired itself out first, not me
I have outlasted all other obstacles and challenges.
And in its wake, appeared the touch and call
As a result, a new opportunity has presented itself.
Of a different breed
This opportunity is different and unique.
One who set to get me wise, and got me there
This person has helped me become wiser and has helped me reach a certain objective.
And then, got me
I am now under this person's influence/control.
And what a thing, to know what could be instead
It's amazing to think about the possibilities that exist.
Oh, what a blessed curse; to see
It's both a blessing and a curse to be able to see what could happen.
It took the agenda from its place in my bed
This opportunity has taken precedence over other plans I had.
Made a merry paramour of me
It has made me very happy and enthusiastic.
Giving me eyes to view it
This opportunity has allowed me to see things differently.
As it goes by the boards
But unfortunately, it may not work out in the end, and I will have to let it go.
O' Sailor, why'd you do it
Asking the Sailor why they took me down this path.
What'd you do that for
Asking for an explanation for their actions.
Saying there's nothing to it
The Sailor made it seem like it wasn't a big deal to follow this path.
And then letting it go by the boards
And then, now I have to let it go.
Contributed by Aaliyah R. Suggest a correction in the comments below.
@mariarombe7109
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 letting 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 letting 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 letting 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 letting it go by the boards
And after waiting, fighting patiently on my knees
All the other stuff tired itself out first, and 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
Oh, 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 letting 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 letting 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 letting 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
@jelly_ellipsis
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 letting 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 letting 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 letting 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 letting 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 letting 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
@dominicomegon4714
People with an ear for music, all in the know, know.. Fiona Apple is UP THERE as the one of the best talents in modern music history.
@lindsaykuzia5038
I've known since i was 12 and i bought her first album with my birthday money.
@melaniep6964
So true, been a huge fan since her first album. She's one of my all time faves.
@grimandbilly005
She's almost as good as Slowdive
@missmac7395
Perfect statement
@desireandfire
Fiona is such a phenomal songwriter it's insane.. the fact that twenty years into her career and she managed to have the most critically acclaimed album last year. This is genuine talent. There's something running in her veins and I'm just so happy to live in a world where she exists
@quillber
"everything good i deem too good to be true. everything else is just a bore" - gosh, she just.. knows
@sculptureofsound2
For me it's the, "everything I have to look forward to has a pretty painful and very imposing before.."
@onehotminutex
I love the mechanics of this song. It really sways like you're on a boat. The video perfectly fits the atmosphere of the song, and not just the sailor reference. This is art.
@bluegenes2273
Good for hula hooping, too!