The Vienna Development Method (VDM) is one of the most mature formal methods, with a history of cost-effective industrial deployment. One important route for this has been the development of robust tools supporting the construction of models, and their animation. We trace the history of this strand of work from the mid-1990s to 2015, taking as our starting point challenges for the industrial usage of formal methods set out by José Nuno Oliveira in 1997. We describe five generations of VDM tools: the IFAD VDM Toolbox, VDMTools, Overture, Crescendo and Symphony, emphasising the influence that the goal of industry usage has had on their features and architectures. We chart the move from a single-formalism tool focussed on executable VDM specifications to a platform for multi-tool analysis of a wider range of models, and look forward to the growth of integrated multidisciplinary toolchains from the ongoing INTO-CPS project. We briefly compare the VDM tool story with the approaches taken by other formalisms that have been applied in industry.