"O' Sailor" is a song written by American singer Fiona Apple and recorded for her third album Extraordinary Machine (2005). On August 15, 2005 (see 2005 in music), 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.