Changes in custodial context, in designation and in display alter the meaning of objects. This article focuses on a collection of figureheads and maps the way their identity as individual works and as a group evolved throughout the course of the twentieth century. Originating as sculptures attached to vessels and integral to seafaring culture, the figureheads charted a very different course when their ‘working lives’ came to an end. Sydney Cumbers assembled his collection of figureheads in the 1920s and 1930s. Displayed privately in the context of a trove of maritime memorabilia, examples were loaned in 1951 to the Black Eyes & Lemonade exhibition of popular art, organized by Barbara Jones and held at the Whitechapel Art Gallery. That year, Cumbers also loaned other figureheads to the Festival of Britain. Acquiring a specific commemorative role after the Second World War, the collection became an ‘unintentional monument’ and, bequeathed to the Cutty Sark Trust, was further embedded in that vessel’s evolution as a national symbol of Britain’s maritime past.