Music video by Fiona Apple performing O' Sailor. (C) 2005 SONY BMG MUSIC ENTERTAINMENT
"O' Sailor" is a song written by American singer Fiona Apple and recorded for her third album Extraordinary Machine (2005). On August 15, 2005, ahead of the album's release in early October, Epic Records made available for streaming both "Parting Gift" and "O' Sailor" on Apple's official website. The following day, the songs were released for digital download at the online iTunes Music Store.
The single's video, directed by Floria Sigismondi, was filmed aboard the RMS Queen Mary 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".