Some time in the early years of the seventeenth century, the city fathers of Gloucester evidently commissioned twelve paintings of past benefactors to that city. The paintings survive in the Gloucester Folk Museum and were exhibited in the spring of 2014 to mark the approximate date of their four-hundredth anniversary. Given the absence of critically important sources that would have given precise information on their commissioning, their origin and history have remained somewhat obscure. This paper nevertheless strives to understand why, and by whom, they may have been painted, and why they remain significant today, both to the City of Gloucester and to the history of English portraiture. It argues that they were commissioned to bolster a sense of community identity and to encourage further benefaction at a time of local hardship and stress. It comments on them as examples of the regional English vernacular style in portraiture of the day, reflects on their current condition and very tentatively suggests who might have painted them.