This article probes the explanatory value of the concept of celebrity capital in helping us to grasp the fate of celebrities and the cultural objects they produce when they move across to other fields. However, the article seeks to do more than this: with reference to the example of the singer-songwriter Bob Dylan’s incursion into the cinematic field, where he co-wrote Masked and Anonymous (M&A) (2003), it contributes to debates by examining the significance of field-specific aesthetic criteria in helping us to gain insight into the aesthetic value of cultural objects. While Dylan’s celebrity capital gave him access to a number of ‘A-List’ celebrity actors, the aesthetic dimension of the film did not have a meaningful relation to the state of play in the cinematic field and so the film was, in the main, critically panned. So, M&A made Dylan’s boundary-crossing journey in reverse: it retreated to the field of popular music where its aesthetic properties were warmly received when considered in relation to Dylan’s wider body of work. Meanwhile, it was difficult for the harshest critics to ignore the aesthetic value that Dylan’s wider body of work had accumulated over time. There is, then, a temporal dimension of aesthetic appraisal that needs to be considered, even when reviews are considered at a particular historical conjuncture. In this analysis of field-specific aesthetic criteria, we see that boundary work is effective in diminishing the status of a cultural object (M&A) but we also see that each critic has only limited sway in the face of the totality of judgements which emerges as a supra-critical voice, heterogeneous and full of contradictions, deriving from all those who make value judgements in the field of culture.