"O' Sailor" is a song written and performed by American singer Fiona Apple and recorded for her third studio album Extraordinary Machine (2005). On August 15, 2005, ahead of the album's release in early October, Epic Records made both "O' Sailor" and "Parting Gift" for streaming on Apple's website. The following day, the songs were released for digital download at the online iTunes Music Store. It was later released to US adult album alternative radio stations on September 12, 2005.
The single's video, directed by Floria Sigismondi, was filmed aboard the and premiered on VH1 on November 7. 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".
Acetate promo CD single:<br /> 1. O' Sailor (Radio Edit) (4:39)<br /> 2. O' Sailor (Album Version) (5:36)