‘Character’ was a key term in the early development of Anthropology as a discipline – Kant gives over the entire last section of his to refining the idea of character as a ‘way of thinking’. Perhaps inevitably, however, its ideological career since then – as the mark of a kind, or type of person – has been highly ambivalent. In the Caribbean, though, the idiosyncratic biographical gaze has loomed large. This article explores the status of character in an urban Caribbean everyday, where the demonstration of character through ‘talkover’ has profound social effects. Where does character come from? And what is its futurity in a social setting where no one can lay claim to autochthony, yet where ‘gifts’ are foundational to the ‘respect’ someone can command? Character belongs partly to the past as ‘a priority’, partly to the future as utopian protention.