"Pirate Jenny," one of the most well-known songs from Kurt Weill's The Threepenny Opera has a long history in contemporary pop and jazz music. In his book, Chronicles, Bob Dylan says of the song, "Each phrase comes at you from a 10-foot drop, scuttles across the road and then another comes like a punch on the chin." Many artists from Nina Simone to Amanda Palmer of the Dresden Dolls have covered it some of whom I'll share here, but first a little backstory:
"The song depicts Jenny, a lowly maid at a crummy old hotel, imaging avenging herself for the contempt received by the townspeople. A pirate ship – with eight sails, and with 50 cannons – enters the harbor, fires on the city and flattens every building except the hotel. The pirates come ashore, chain up all the townspeople, and present them to Jenny, who orders the pirates to kill them all. She then sails away with the pirates.
The song was originally placed in the first act and is sung by Mackie's bride, Polly Peachum, who resents her parents' opposition to her trying her luck with Mackie and is phantasising about avenging herself on the constraints of her family. However, the song is frequently moved to the second act and given to the prostitute Jenny. Jenny has given Mackie, her former lover, shelter from the police but is jealous of his wife, Polly. Eventually, she tips of the police, who catch Mackie and take him to his hanging. Her song suggests that she likes the idea of having Mackie's fate in her hands." (Wikipedia)
One of the most revered versions is Nina Simone's. From 1964's Nina Simone in Concert, she gives the song "a grim civil rights undertone, with the 'black freighter' symbolizing the coming black revolution."(Wikipedia) Says nojojo from Alas, A Blog: "She means every word of it, too — you can hear that in her voice. The first time I listened to it, I thought, If I was white, I would sleep with one eye open. For the rest. Of. My. Life. Because it’s blatantly obvious from the barely-contained rage in this song that Simone is not singing about pirates..."
I dug around youtube and found several other versions from the sublime to the just plain odd. Here are some of my favorites: