Tracing the collaboration between Dylan and Scorsese from the 1960s on to the Netflix original ‘The Rolling Thunder Revue: A Bob Dylan Story by Martin Scorsese’ (2019), this article argues that the mutual respect of the two artists rests on a shared contestation of borders between fact and fiction. In the spirit of romanticism, both Dylan and Scorsese manage to maintain their unique style as they continue to create new teams as well as audiences.