Singing may be a relative strength for people with dementia, yet little is known of how individuals leverage it as a communicative resource in everyday interaction. This study analyzes how Dan, a man living with vascular dementia, modifies lyrics based on prior talk and the physical environment during interactions with his wife, Morgan. Using Conversation Analysis, I describe the emergent structure of his singing and what it accomplishes. Dan uses singing to do a range of interactional jobs (such as complimenting, complaining, and requesting), and his lyrics are susceptible to evaluation based on their construction and relevance to previous talk. Both participants treat his singing as humorous and creative wordplay, but the laughability of his singing is contingent on how he modifies the formulaic lyrics based on the current discursive context. Thus, singing is a way in which Dan situationally constructs himself as a funny, clever, and sociable person. Dan’s singing also indirectly indexes his close relationship with Morgan by assuming her shared musical knowledge. This analysis contributes to the study of identity construction by people with dementia, the understanding of how people adapt to changes in cognition, and the study of the structure and function of singing in everyday interaction.