He eschewed conventional opera for the type of music theater that more completely integrated music with drama, dialogue with song and movement. He first collaborated with the playwright Bertolt Brecht in 1927 in a Baden-Baden production of the Mahagonny Songspiel, but it was Weill's Die Dreigroschenoper ("The Threepenny Opera"), with text by Brecht, that made him an overnight international sensation. A modernization of John Gay's "The Beggar's Opera" (1728), the work's explicitly socialist libretto was set by Weill to music that borrowed from jazz and the concert hall. Their next successul collaboration, another satire on capitalist society, Aufstieg und Fall der Stadt Mahagonny ("The Rise and Fall of the City of Mahagonny)", has seen recent revivals in the major opera houses of the US and Europe.
Weill and his wife Lotte Lenya fled Nazi Germany in 1938 for America via Paris where he met up with Brecht with whom he wrote the song cycle Die sieben Todsünden ("The Seven Deadly Sins"). It was to be their last collaboration. For the rest of his life, Weill lived in America where he composed music for Broadway and later for Hollywood. Although he wrote a number of successful musicals, none achieved the immense popularity of "The Threepenny Opera." "The Street Scene," which is being staged by regional opera houses today, is considered to be his American masterpiece.