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O’ Sailor

Fiona Apple

Extraordinary Machine (2005)

If you’re familiar with Fiona Apple, you probably know the story of ”Extraordinary Machine” – originally recorded in 2003, never released, then leaked, then re-recorded for a 2005 official release. The end result is two near-equally sublime albums, so much so that it was really hard to pick one particular song as a stand-out. But it ended up being “O’ Sailor” that resonated with me the most. It coincided with a particularly rough romantic period of my life, and lines like “everything I have to look forward to / has a pretty painful and very imposing before” spoke to my melancholy. Apple is one of the most clever lyricists of our time, and it’s a gift that she’s an equally talented singer and pianist. Too bad this was her only album during the whole decade.

Also check out: The original unreleased version of Apple’s “Used to Love Him” – an angrier counterpart to “O’ Sailor.”