This chapter charts the history of cultural management from the 1980s to the present. The first phase, beginning with the professionalisation of arts management in the 1980s, is described as ‘Cultural Management 1.0’, which positioned managers outside and above artistic processes, administering creative outcomes but not intervening in creative processes. ‘Cultural Management 2.0’ describes a shift to a more entrepreneurial, integrated management approach which reflected the ‘creative industries’ rhetoric in cultural policy, starting from the UK in 1998. Finally, ‘Cultural Management 3.0’ refers to the rising importance of co-creation, user experience and fan communities in a digital creative economy, requiring managers to work more collaboratively and democratically. The chapter argues that these different phases overlap, with each model attempting to resolve some of the paradoxes at the core of cultural management – the unmanageability of cultural people and processes, the need to be both entrepreneurial and strategic, the changing role of audiences as both receivers and producers of meaning. By identifying and understanding underlying assumptions and dilemmas, we can bridge between these models, tailoring an approach to fit our own purpose and situation.