I'm undecided about you again
Mightn't be right that you're not here
It's double-sided, because 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

Oh 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

Oh 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 because 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

Oh 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

Oh 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

Oh 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
Oh sailor, why'd you do it
What'd you do that for
Giving me eyes to view it
As it goes by the boards



Lyrics submitted by SongMeanings, edited by Mellow_Harsher

Track duration: 05:36


O' Sailor song meanings
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  • 0
    Song Meaning:i don't think it's about a guy or love. it seems to be about her relationship with her record label/managers/the music industry.

    first para: about her love/hate relationship with the scene. she misses not having the spotlight on her work, but she hates the 'money before creativity' aspect probably shoved by her label. and she 'ruined' it all because she is vocal about this aspect of the music business. remember the mtv awards speech?

    2nd para: it's about her neurosis. how difficult it is to maintain her independence, but she pulls through.

    the chorus: it's interesting. the sailor reference is because she knows how fickle the music industry is. one moment you're loved, the next you're replaced by someone new. just like a sailor who lands and finds a partner and leave them for another one in their next venture. the line 'going by the boards' is about the cancelled albums and being put on the shelves. the label says 'there's nothing to it,' then not fall through with their plans.

    3rd para: she knows you have to play the game to be in the business, but she plays her own game (i have too been playing with 52 cards), and she is open about her path, or how she plays the game - uncompromising in her vision and creativity for all to see, not so much about being a manufactured pop princess, and she gives it all or nothing, take it or leave it. hence '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'

    4th para: she sticks to her guns and not sell out, and she sort of wins, because her loyal fans established the free fiona campaign and got her album out. though she didn't make a huge publicity campaign to go against her label for trying to change her, hence the waiting, ffighting patiently on her knees line. (And after waiting, fighting patiently on my knees. All the other stuff tired itself out first, not me) the label relented to the fans and her patience paid off. but i guess eventhough she tries to keep her work intact to how she originally wants it to be, i guess she did have to make some minor alterations here and there to please the label, so it comes off as 'a different breed' (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.)

    5th para: she is very disappointed to know that if she did exactly what the label wants they'll keep her star shining brightly, since that's the best way to market an 'artist' (And what a thing to know what could be instead
    Oh, what a blessed curse; to see) again, she sees it, but she won't commit to being a 'product'. and she thought this relationship was a mutual one, and that the label understands she is not one of those artists who will crank up some silly tune just for a quick buck, but instead the label moved on to other commercially viable artist (IT took the agenda from ITS place in my bed. Made a merry paramour of me)
    Flag jessmackon February 28, 2012   Link
  • 0
    General Comment:also, the ambivalence I mentioned is clearly introduced when she says:

    It's double-sided, cause I ruined it all
    but also saved myself, by never believing you, dear
    Flag alovelyfadeouton June 10, 2008   Link
  • 0
    General Comment:fantastic song. I think the abandon with which she sings it alludes to the theme of habit. that this is some kind of habitual behavior or situation that she's used to--because of everything having a painful "before" she ends up in these relationships where she is the one inflicting the pain instead (being the other woman, as opposed to the woman being cheated on). The repetition of her asking the sailor why he did it seems as though she is both resentful that he hurt her in the end instead of the woman that he was supposed to be hurting, and also that she sort of expected it (at least her tone suggests that she's not really surprised in the end and instead is just going through the protocol of asking why, even though she expected it all along). i think the thing i like most about this song is that ambivalence between being really hurt and it being expected; really wondering why, and asking why in a sort of sarcastic/cliche way that everyone asks even when they already know the answer.
    Flag alovelyfadeouton June 10, 2008   Link
  • 0
    General Comment:does anyone else, notice the creative writing of the LYRICS?
    Flag ddark13on May 23, 2008   Link
  • 0
    General Comment:The Jon Brion-produced version is great. Just great! ...he's a genius.
    Flag el_chisoon March 18, 2008   Link
  • 0
    General Comment:or i also found:

    go by the board (British, American & Australian, American)

    if something that has been planned or arranged goes by the board, it does not happen, and if something that exists goes by the board, it ends.
    Flag tinatinoon March 05, 2008   Link
  • 0
    General Comment:"go by the boards"

    meaning: become less important, be neglected or omitted
    Flag tinatinoon March 05, 2008   Link
  • 0
    General Comment:Has anyone heard Fiona say, in an interview or something, that this is homage to the Beach Boys? Musically, there's a certain kinship to that song off the BB's "Holland" album. Either that or I must be crazy!
    Flag sonztwinon May 25, 2007   Link
  • 0
    General Comment:I Absolutely adore this song!Its been in my IPod ever since the new album came out(2 freggin years ago!) its probably my favourite fiona apple song. the lyrics, the meaning, the smoky piano, amazing!
    I don't know why but i think that its supposed to be a dreamy song, like fiona didnt really mean that much about "mistresses" and "wifes". i dont know.

    To be honest, if someone doesnt know Fiona and wanted to get something off her songs to understand that human being, it would probably be

    "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"
    and i can really, really, terribly relate to that.maybe thats why this song is my all time favourite fiona apple song!

    The part where she says "i have too been playing with 52 cards..." it means that she is doing her best to forget that it ever happened and get over the sailor, hence "what could i do but spend my best", however she fails to get over him "All the other stuff tired itself out, not me". What a heart-wrenching song..Absolutely a favourite!

    And i must disagree with you guys, the first version of "o' sailor" is very boring and Fiona sang it in a really cold way as if she couldnt wait to get it over with, the vocals and the piano of the new version are unlike anything ive heard before!

    We can go on and on explaining this song, but to me its just one of those songs u put on at 2am in the morning when ur tired of the world and just feel...Fiona i feel for you!
    Flag Hotel-Paperon May 23, 2007   Link
  • 0
    General Comment:I think the reason a lot of people are saying she sings with no passion is because they have the official release. The original version, the one produced by Jon Brion, puts everything on the official release to shame. It's amazing how Mike Elizondo managed to take all of the warmth out of this album and make Fiona sound so detached all the time.

    So, get online and download the bootleg. I'll never understand why Sony shelved the only bearable version of this album, and then released Elizondo's horrendous reworking.
    Flag aydiosmioon March 18, 2007   Link

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