This article presents a variationist analysis of the bought vowel in New York City English (NYCE) and finds that it has reversed the trajectory of change outlined in Labov (1966). An acoustic analysis of production data from sixty-four native residents of the Lower East Side demonstrates that bought is lowering in apparent time, a change led by young people, white and Jewish speakers, and the middle classes. A second source of data comes from perceptions of raised bought gathered from a matched guise experiment, which highlights an indexical field (Eckert 2008) of social meanings for raised bought that comprise a ‘classic New Yorker’ persona: an older, white ethnic New Yorker from the outer boroughs who is mean and aloof. Taken together, the data suggest that bought's reversal is motivated by its contemporary social meanings. (bought, New York City English, dialectology, variationism, sound change, social meaning, perception, sociophonetics)*