This was written by Suzanne Vega in 1978. In the song, Vega assumes the voice of the sea nymph Calypso, who saved the drowning Ulysses and waylays him on her island for 7 years as she is in love with him. Eventually Zeus sends Hermes, the messenger of the Gods, to tell Calypso to release Odysseus, which Calypso reluctantly does. The story is taken from Homer's Odyssey.
Suzanne Vega said of this song: "Calypso makes an appearance on the first page [of Homer's Odyssey] and I guess she never really comes back, and no one ever checks up on her to see how she's doing. It's very one sided, I remember feeling that. So this song is called Calypso and it's written from her point of view the night before he left."
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