Comedians play an important role in society and public debate. While comedians have been considered important cultural critics for quite some time, comedy has acquired a new social and political significance in recent years, with humour taking centre stage in political and social debates around issues of identity, social justice, and freedom of speech. To understand the shifting meanings and political implications of humour within a Dutch context, this PhD thesis examines the political and aesthetic workings of humour in the highly popular Dutch cabaret genre, focusing on cabaret performances from the 1960s to the present. The central questions of the thesis are: how do comedians use humour to deliver social critique, and how does their humour resonate with political ideologies? These questions are answered by adopting a cultural studies approach to humour, which is used to analyse Dutch cabaret performances, and by studying related materials such as reviews and media interviews with comedians. This thesis shows that, from the 1960s onwards, Dutch comedians have been considered ‘progressive rebels’ – politically engaged, subversive, and carrying a left-wing political agenda – but that this image is in need of correction. While we tend to look for progressive political messages in the work of comedians who present themselves as being anti-establishment rebels – such as Youp van ‘t Hek, Hans Teeuwen, and Theo Maassen – this thesis demonstrates that their transgressive and provocative humour tends to protect social hierarchies and relationships of power. Moreover, it shows that, paradoxically, both the deliberately moderate and nuanced humour of Wim Kan and Claudia de Breij, and the seemingly past-oriented nostalgia of Alex Klaasen, are more radical and progressive than the transgressive humour of van ‘t Hek, Teeuwen and Maassen. Finally, comedians who present absurdist or deconstructionist forms of humour, such as the early student cabarets, Freek de Jonge, and Micha Wertheim, tend to disassociate themselves from an explicit political engagement. By challenging the dominant image of the Dutch comedian as a ‘progressive rebel,’ this thesis contributes to a better understanding of humour in the present cultural moment, in which humour is often either not taken seriously, or one-sidedly celebrated as being merely pleasurable, innocent, or progressively liberating. In so doing, this thesis concludes, the ‘dark’ and more conservative sides of humour tend to get obscured.