The song depicts Low-Dive Jenny, a character based on Jenny Diver. Low-Dive Jenny is a lowly maid at a "crummy old hotel", imagining avenging herself for the contempt she endures from 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 sung by Mackie's bride, Polly Peachum, who resents her parents' opposition to her trying her luck with Mackie and is fantasizing 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 off 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.
Clifford Harper drew a graphic adaptation of the song, entitled "The Black Freighter" in the magazine Anarchy No. 2.
Comic-book writer Alan Moore cited this song as one of the inspirations for the Black Freighter pirate material in Watchmen. The Nina Simone version also appears on the. In the 2019 TV series, Jessica Camacho portrays "Pirate Jenny", a member of the Tulsa police.
In , also written by Alan Moore, Jenny's revenge fantasy is taken as a literal event in which "Janni", who is Captain Nemo's daughter, is gang raped and summons the crew of the Nautilus to slaughter her rapists and the indifferent spectators alike.
The song was inspiration for Lars von Trier's Dogville, a film about a mistreated woman who seeks revenge on her neighbors.
The song is paraphrased on Chico Buarque's "Geni e o Zepelim". This song is a number from his musical playÓpera do Malandro, which is based on Brecht's The Threepenny Opera. In Chico's version, Jenny ends up saving the city, just to be despised immediately after.
The song is mentioned in Bon Iver’s 2019 track “U ” on the albumi,i.
Sasha Velour performed a version of the song, with lyrics altered to be about drag, in their short filmPirate Jenny, the first of their 2018 anthology One Dollar Drags.
