Can we provide legislative drafters with tools to simplify and clarify legislation, and make it more accessible? In the UK, USA, Canada, Australia and EU, through strategies such as the ‘Plain Language’ and ‘Good Law’ (PL/GL) initiatives, it is claimed that the answer is ‘yes’. Though many of the normative intentions underlying such initiatives are commendable, we argue that the pursuit of legislative and legal simplicity, clarity, and accessibility ignores the distinctly ‘complicated’ and ‘complex’ role of legislation and legislative drafters. This leads to a range of contradictory and paradoxical outcomes that undermine these goals. Following a review of the role of legislative drafters and PL/GL initiatives, we use a complexity tool, the Stacey Diagram, to demonstrate and visualise the inherent tensions in the PL/GL position. We show how legislative drafters negotiate their complex environment in a much more subtle, human way than is commonly recognised in PL/GL discourse.