In October 2013 during a fractious interview with Jeremy Paxman for the Newsnight TV programme, the comedian Russell Brand called for a revolution against a self-serving political and economic elite. Over the following 18 months Brand became a prominent Left-wing political figure in the UK This paper suggests that Brand’s experience was not isolated but forms part of a wider contemporary trend of comedians becoming populist political leaders. Other examples include the French comedian Dieudonné and the Italian comedian Beppe Grillo, whose political party Movimento 5 Stelle is currently the largest in the Italian Parliament and part of the governing coalition. Using Brand as a case study the paper examines his political storytelling for its structure and mode of deployment. Whenever Brand ventures forward a sincere statement he always stands ready to ironize it in order to avoid the perception of piety. Using Peter Sloterdijk’s discussion of cynical reason and Slajov Zizek’s concept of cynical irony I suggest that a post-political ironic detachment has become the dominant mode of ideology. I then argue that this ironic detachment has come under increasing pressure since the economic crisis of 2008 and the increased political engagement it has provoked. It is within this aspect of the conjuncture that we can position the discourse about a Post-Truth era and Post-Truth leaders. The comedian as political leader, I argue, shows a particular route through this problem. They represent transitional figures pioneering the shift from ironic detachment to postironic statements and narratives of political sincerity of the kind that sustained political engagement requires.