In December 2019, the New Zealand AIDS Foundation (now the Burnett Foundation) released a public health campaign raising awareness about the increasing rates of syphilis infections in New Zealand. The campaign consisted of photographs that contrasted contemporary backgrounds of bars and nightclubs with actors wearing theatrical costumes akin to the Elizabethan period. This reinforced the perceived idea that syphilis was a disease resurging from the distant past. This paper discusses one of the campaign’s most iconic portraits by analysing its shared cultural, artistic, and medical references (explicit or implicit) and their shifting meanings through time.