O Sailor
Fiona Apple Lyrics


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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

Overall Meaning

The lyrics to Fiona Apple's song "O' Sailor" demonstrate the singer's ambivalent feelings towards a past lover who has come back into her life. She is "undecided" about whether it's right that he's not there, and she acknowledges that her own actions have contributed to the demise of their relationship. Yet, she has also "saved herself" by not believing him, showing that she has learned to protect herself from further heartbreak. The chorus focuses on the question of why the sailor (her lover) has acted the way he has, saying there's "nothing to it" before "letting it go by the boards." This could refer to his lack of commitment or perceived indifference.


The song's second verse highlights her own vulnerability in relationships, suggesting that the reason she has been hurt in the past is that she has given too much of herself too soon. She describes herself as "playing with fifty-two cards," wearing her heart on her sleeve, giving her all even when she should be guarded. Yet, despite this, she feels she has nothing to lose in love, and will continue to "spend her best."


The final verse of "O' Sailor" is more optimistic than the rest of the song, with Fiona Apple singing about a new lover who "got [her] wise" and "made a merry paramour" of her. This suggests that she has found a healthier relationship with someone who values her for who she really is. The repetition of the chorus shows that she is still trying to understand her previous lover's actions, but also acknowledges that she has been given the gift of new perspective in her current relationship.


Line by Line Meaning

I'm undecided about you again
I'm not sure if I want to be around you or not


Mightn't be right that you're not here
It doesn't feel right that you're gone


It's double-sided 'cause I ruined it all
I messed up our relationship, but it was for the best


But also saved myself
I also saved myself from being hurt


By never believing you, Dear
I never believed in your promises


Everything good I deem too good to be true
I never trust things that seem too perfect


Everything else is just a bore
Everything else seems uninteresting


Everything I have to look forward to
The future holds pain and challenges for me


Has a pretty painful and very imposing before
I know that there will be pain and hardship ahead


O' sailor why'd you do it
Why did you do what you did


What'd you do that for
Why did you hurt me like that


Saying there's nothing to it
Acting like it wasn't a big deal


And then lettin' it go by the boards
And then forgetting about it


I have too been playing with fifty-two cards
I've been taking risks and not holding back


Just cause I play so far from my vest
Because I'm not afraid to show my cards


Whatever I've got, I've got no reason to guard
I have nothing to hide, so I don't hold back


What could I do but spend my best
I do my best with what I have


Giving me eyes to view it
You helped me see the truth


And after waiting, fighting patiently on my knees
I waited and fought for what I wanted


All the other stuff tired itself out first, not me
I didn't give up, I kept going


And in its wake appeared the touch and call of a different breed
Something new and better came along


One who set to get me wise and got me there and then, got me
Someone who showed me the truth and helped me grow


And what a thing to know what could be instead
It's amazing to see what could be instead of what was


Oh what a blessed curse to see
It's a blessing and a curse to have this knowledge


It took the agenda from its place in my bed
It changed my priorities in life


Made a merry paramour of me
It made me happy and full of love




Lyrics © BMG Rights Management
Written by: FIONA APPLE MAGGART

Lyrics Licensed & Provided by LyricFind
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Most interesting comments from YouTube:

@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



All comments from YouTube:

@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

11 More Replies...

@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!

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