Ella Fitzgerald performing in 1958
Ella Fitzgerald performing in 1958 at Chicago nightclub Mister Kelly’s © Yale Joel/Getty Images

At the heart of the story of “Mack the Knife” is a great irony: a song about a cold-blooded serial murderer written by a Marxist playwright and a leftwing composer for a musical that aimed to lay bare the hypocrisies of bourgeois morality went on to become a huge commercial success globally, especially in the US. It was even used in a 1980s advertising campaign for McDonald’s hamburgers (“Mac tonight”).

Bertolt Brecht and Kurt Weill’s The Threepenny Opera, which was based on John Gay’s The Beggar’s Opera of 1728, opened in Berlin in 1928. Brecht and Weill’s work sets the action in Victorian London where the villain, Macheath, goes about his dastardly business.

With only a few days to go before the show opened at the Theater am Schiffbauerdamm (featuring Weill’s wife Lotte Lenya as Jenny Diver), the production’s egotistical star Harold Paulsen, playing Mackie, insisted that he be given a grand introduction. So Brecht and Weill quickly wrote a scene-setting Moritat (murder ballad), with barrel-organ accompaniment, bigging up the dreadful deeds of Mackie Messer (“Mack the Knife”).

Audiences were slow to respond to a show that was neither musical nor opera but a new, jazz-influenced amalgam. However, The Threepenny Opera eventually caught on and was performed more than 400 times in the next two years. The rise of Hitler forced Brecht and Weill into exile; in 1938 Weill was labelled a composer of “degenerate music” in the Düsseldorf exhibition that followed the previous year’s show of “degenerate art”.

After the second world war The Threepenny Opera crossed the Atlantic, running in 1952 at Brandeis University, Massachusetts, conducted by Leonard Bernstein (with lyrics translated into English by Marc Blitzstein), before opening off-Broadway in 1954 (again featuring Lenya). In its passage to the US, something happened to “Mack the Knife”: where the German-language original has a dirge-like quality, in the US it became the jaunty tale of a roguish gangster.

'Mack the Knife' vinyl record

It was Louis Armstrong who pushed “Mack the Knife” into the jazz repertoire in 1955, having been encouraged by a Columbia Records executive to cover it, and he established the template for versions that followed. Some of Mackie’s deeds were omitted — the original tells of a woman being raped by Mackie in her sleep.

Nevertheless, Blitztein’s translated lyric is brilliantly vivid: “Scarlet billows start to spread.” The word “dear” (and, later, “babe”) was added to help the lyrics to scan. Armstrong also ad-libbed a mention of Lotte Lenya to the song’s roll-call of victims, and her name has stuck ever since.

In 1959 Bobby Darin took the song by the scruff of the neck and turned it into the swing classic widely known today. Unlike the Brecht-Weill original, which remains in the same key throughout, Darin’s version changes key, chromatically, no fewer than five times, ratcheting up the tension.

By now the song had become a standard, open to all-comers including Frank Sinatra and Peggy Lee. Ella Fitzgerald and Duke Ellington recorded a blistering version at the Jazz à Juan festival in 1966; as well as scatting sensationally, Fitzgerald trumps Darin with 11 key changes.

Notable German-language versions, meanwhile, were performed by Lotte Lenya herself back in the 1930s, and more recently by Ute Lemper, whose sinister reading features a cascade of rolled Germanic “r”s. Nick Cave recorded a memorably chilling version; he sings in English but references the song’s German roots with his oompah arrangement.

But a real flavour of the song’s origins can be found in GW Pabst’s 1931 film of The Threepenny Opera. As Mackie skulks among the crowds, our singer-narrator — using a kind of flip-chart of Mackie’s crimes — intones the song with deadpan dread, to the mournful, scraping accompaniment of the barrel-organ. Here, Mackie is no caricature gangster but a nasty piece of work.

For more in the series, and podcasts with clips — including one on David Bowie’s ‘Starman’ — go to ft.com/life-of-a-song

Photograph: Yale Joel/Getty Images

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