Sydney Theatre Company knows cutting edge, but it’s unlikely they’ve seen an antihero as dangerous as Mack the Knife in Michael Kantor’s new production of The Threepenny Opera, which updates the action to a seedy Australian locale.

It’s an apt transformation, considering Bertolt Brecht adapted John Gay’s The Beggar’s Opera — set in dank, Dickensian London — to create an unflinching reflection of Weimar Republic debauchery.

Kantor, who created the production for Melbourne’s Malthouse Theatre in collaboration with Victorian Opera, believes Australia’s convict roots have primed us to cheer on a murderous deviant like Macheath. “Melbourne and Sydney are cities that really revel in and glorify our criminality we get off on it.

“The sheer mention Smith Street in Melbourne and you’re thinking about the hoodlums and the history of crime written all over that street. Sydney has a similar relationship; just mention the Cross and it’s all in the geography of the place. Underbellycalls upon that and we do as well.”

Although Brecht’s lyrics have been translated from the original German to a bawdy English vernacular, they’re still perfectly suited to Kurt Weill’s biting, jazz-inflected tunes. Kantor worked “hand in glove” with Victorian Opera artistic director...