Cornish tenor Charles Incledon (1763–1826) was a prominent figure in Britain during the Napoleonic Wars, entertaining patriotic crowds with popular naval ballads. Unlike other nationalistic singers of the period, Incledon did not merely masquerade in a sailor’s costume on stage – he was an authentic sailor. Despite his popularity, Incledon was an especially problematic figure. His complex masculinity was the crux of this problem. Although some saw the tenor as a brave British Tar, others imagined him as a stereotypical Georgian sailor – a rough and ready character with a penchant for women and grog. His identity was complicated yet further by his status as a singer – a profession that was characterised as feminine and foreign in nineteenth-century Britain. Incledon’s masculinity was therefore intriguingly multi-faceted and contradictory. He was at once a brave British Tar, a Regency rake, an effeminate showman and a figure of ridicule. This chapter draws on a wide range of multimedia sources to examine the various strands of Incledon’s masculinity, focusing especially on the ways in which the singer attempted to present himself. An analysis of Incledon’s reception reveals much about contemporary attitudes towards naval masculinity.