This short case study explores the problems of identifying and selecting disparate objects in the context of the post-war planned urban landscape of Glenrothes. More than 140 art works, of various scale and type, are located in the townscape and all of these have been considered recently for statutory designation by Historic Scotland, an executive agency of the Scottish Government. Glenrothes, in Fife, was designated in 1948 under the New Towns (Scotland) Act 1946 as Scotland’s second post-war New Town, after East Kilbride in 1947. The original plan was to build a new settlement for a population of around 34,000. Careful consideration was given to the form and infrastructure of the town, focusing on individual suburban neighbourhoods (known as precincts) each with their own identity. Engineers, builders, and architects worked together to not only to create good quality mass housing but also conceived green spaces, tree planting and hard and soft landscaping. By its 20th anniversary, the Glenrothes Development Corporation adopted a pioneering approach to ensure a lasting sense of place and identity for a town that had experienced the ebb and flow of its first generation of residents by appointing its very own Town Artist in 1968. This was the first appointment of its kind in the country, arousing widespread interest in the UK and abroad thereafter.