“Sail Away” – Randy Newman

Video

Easily one of the most despairing and devastating songs ever written, “Sail Away” is a song written from the perspective of a slave trader extolling the virtues of America to a group of Africans back in the 1800s to lure them aboard ships. As much as the lyrics present America as a land of endless fun and opportunity, the sad, plaintive piano arrangement speaks otherwise. One of Randy Newman’s best songs, “Sail Away” proves that satire doesn’t always have to be “funny” to be effective. It can sometimes make you shiver with fear and sadness.