The presumed portrait head presented here was found in Noviomagus / Neumagen (Kr. Bernkastel-Wittlich). It is likely that it was part of a funeral monument dating to the early 3rd century AD. It pictures a bearded middle-aged man with a unilateral cleft lip on the left side (ICD 10 Q 36.9), probably representing the first portrayal in the Roman era of this congenital malformation of the face that is quite frequent today. This paper discusses the problem of cleft lips and cleft lip-jawbone-palates in (Roman) antiquity, consulting medical, osteoarchaeological, iconographic and historic-epigraphic sources. Concluding an attempt is made to reconstruct major stages in the life of a human with such a cleft.