Suzanne on her motivation to write "Calypso":
"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."
In concert: London School of Economics, England, October 24, 1985

From Hugo Westerlund's "Suzanne Vega FAQ" (http://www.vega.net/faq/index.htm):
This song is another perspective-taking one. Calypso is a nymph in Greek mythology who appears in Homer's Odyssey. She is the daughter of Atlas, the giant who holds up the sky, and she lives on the mythical island of Ogygia. It is there she has taken Odysseus (Ulysses) after having saved him from drowning in the angered waves of the sea god Poseidon after his ship has been struck by Zeus' thunderbolt. Calypso keeps him there on her lusciously wooded island as her captive lover for seven years. But despite the beautiful woman's love, he cannot forget his own country, the rocky island of Ithaca, and his clever and faithful wife Penelope. After an intervention by the council of the gods, especially the powerful, bright-eyed Athena, Calypso must finally let Odysseus leave.
This song is about the dawn on the day that the man she loves will leave her. She has even helped him to build the craft that will carry him away from her, and remembering the sweet and salty pleasures that will no longer be hers to enjoy, she stoically tries to accept her lonely future.
In the very beginning of the Odyssey, Homer describes how king Odysseus is caught on Calypso's island, several years after the sack of Troy, where he had taken part as an allay of the Greek overlord Agamemnon. For those of us who are unfortunate enough not to know classical Greek, here is an excerpt from E.V. Rieu's prose translation of 1946 (Book I, 11-21): All the survivors of the war had reached their homes by now and so put the perils of battle and the sea behind them. Odysseus alone was prevented from returning to the home and wife he longed for by that powerful goddess, the Nymph Calypso, who wished him to marry her, and kept him in her vaulted cave. Not even when the rolling seasons brought in the year which the gods had chosen for his homecoming to Ithaca was he clear of his troubles and safe among his friends. Yet all the gods were sorry for him, except Poseidon, who pursued the heroic Odysseus with relentless malice till the day when he reached his own country.
Later, in Book V, Hermes, the messenger of the gods, travels to Calypso's island, where he tells the nymph of Zeus decision that she has to let Odysseus go: The divine Calypso listened in fear and trembling. When he [Hermes] had done, she unburdened her heart: 'A cruel folk you are, unmatched for jealousy, you gods who cannot bear to let a goddess sleep with a man, even if it is done without concealment and she has chosen him as her lawful consort. You were the same when Rose-fingered Dawn fell in love with Orion. Easy livers yourselves, you were outraged at her conduct, and in the end chaste Artemis rose from her golden throne, attacked him in Ortygia with her gentle darts and left him dead. And so again, when lovely Demeter gave way to her passion and lay in the arms of her beloved Iasion in the thrice-plowed fallow field, Zeus heard of it quickly enough and struck him dead with his blinding thunderbolt. And now it is my turn to incur the same divine displeasure for living with a mortal man - a man whom I rescued from death as he was drifting alone astride the keel of his ship, when Zeus had shattered it with his lightning bolt out on the wine-dark sea, and all his men were lost, but he was driven to this island by the winds and waves. I welcomed him with open arms; I even hoped to give him immortality and ageless youth. But now, goodbye to him, since no god can evade or thwart the will of Zeus. If Zeus insists that he should leave, let he be gone across the barren water. But he must not expect me to transport him. I have no ship, no oars, no crew to carry him so far across the seas. Yet I do promise with a good grace and unreservedly to give him such directions as will bring him safe and sound to Ithaca.' So when Hermes has left, Calypso goes to find Odysseus: She found Odysseus sitting on the shore. His eyes were wet with weeping, as they always were. Life with its sweetness was ebbing away in the tears he shed for his lost home. For the Nymph had long since ceased to please. At nights, it is true, he had to sleep with her under the roof of the cavern, cold lover with an ardent dame. But the days found him sitting on the rocks or sands, torturing himself with tears and groans and heartache, and looking out with streaming eyes across the watery wilderness. Calypso tells Odysseus that she will let him go, but he mistrusts her and makes her swear a solemn oath that she "will not plot some mischief against" him. This the beautiful nymph does smilingly while gently stroking his head with her hand. Later, she makes a lame attempt to persuade him to stay, but he is determined to go, and after a night in the cavern, where "in each other's arms they spent a night of love", she helps him to build a small ship:By the end of the fourth day all his work was done, and on the fifth beautiful Calypso saw him off from the island. The goddess had bathed him first and fitted him out with fragrant clothing. She had also stowed two skins in his boat, one full of dark wine, the other and larger one of water, besides a leather sack of corn and quantities of appetizing meats. And now a warm and gentle breeze sprang up at her command.
There Homer leaves Calypso to mourn alone on her island, while we hear that "it was with a happy heart that the good Odysseus spread his sail". Almost three thousand years later, Suzanne Vega took pity on the poor nymph and gave her mourning a voice.