O' Sailor

Album: Extraordinary Machine (2005)
Play Video

Songfacts®:

  • This song is about being in mourning, although what it is over, Apple doesn't make clear. Some of the lyrics suggest a death, and some seem to be about a man being unfaithful. It could possibly even be both. The song and video have an eerie "ghost ship" type of effect. >>>
    Suggestion credit:
    Angela - Sylacauga, AL
  • When Fiona sings:

    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


    "By the boards" is an expression meaning cast aside. It's a sailing term meaning something being thrown overboard as useless - it would go by the boards as it went past the ship.
  • Extraordinary Machine was Apple's third album. It was finally released in 2005, six years after her previous LP, When The Pawn... She started recording the album in 2003 with Pawn producer Jon Brion, but they could only complete two tracks to their satisfaction: the title track and "Waltz (Better Than Fine)," which ended up being the first and last songs on the album. The other nine tracks they worked on stagnated; Mike Elizondo was brought in to take over production, and it still didn't gel. With production at a standstill, Brion's roommate, a producer named Brian Kehew, began surreptitiously recording new versions of the tracks with Fiona without the record company knowing. They were able to complete the unfinished nine tracks, plus another that Fiona brought in called "Parting Gift." (Here's Brian's full story about making the album.)

Comments: 2

  • G from Cleve, AndorraNope, it is about being the other woman.
  • Shane from Anaheim, CaThe music video for this song was filmed on the Queen Mary in Long Beach, CA.
see more comments

Editor's Picks

Michelle Branch

Michelle BranchSongwriter Interviews

Michelle Branch talks about "Everywhere," "The Game Of Love," and her run-in with a Christian broadcasting network.

Part of Their World: The Stories and Songs of 13 Disney Princesses

Part of Their World: The Stories and Songs of 13 Disney PrincessesSong Writing

From "Some Day My Prince Will Come" to "Let It Go" - how Disney princess songs (and the women who sing them) have evolved.

N.W.A vs. the World

N.W.A vs. the WorldSong Writing

How the American gangsta rappers made history by getting banned in the UK.

Jesus Christ Superstar: Ted Neeley Tells the Inside Story

Jesus Christ Superstar: Ted Neeley Tells the Inside StorySong Writing

The in-depth discussion about the making of Jesus Christ Superstar with Ted Neeley, who played Jesus in the 1973 film.

Real or Spinal Tap

Real or Spinal TapMusic Quiz

They sang about pink torpedoes and rocking you tonight tonight, but some real lyrics are just as ridiculous. See if you can tell which lyrics are real and which are Spinal Tap in this lyrics quiz.

Song Cities

Song CitiesMusic Quiz

Nirvana, Billy Joel and Bruce Springsteen are among those who wrote songs with cities that show up in this quiz.