This article examines the politics of the Neapolitan rap band 99 Posse. Growing up in a city characterised by high unemployment and crime, individual band members independently gravitated towards far left politics, and emerged in late 1991 as the house band of the ‘Officina99’, an autonomist squat in the east of the city which gave the group its name. This article examines their political commitment through their songs, covering subjects from youth unemployment to the exploitation of casual workers. Another theme is how, over a decade, their initial denunciation of ‘communism’ mutated into sympathy. It is argued that the reason for their huge success – apart from their rather controversial decision to sign up with a major multinational such as BMG – lies in their ability to make these themes relevant to disaffected young people.