This chapter explores some of the issues of adaptation and dramaturgy that underlie the progress of Federico Fellini's original film from screen to the musical stage and back to the screen again. Through examination of two stages of adaptation, and comparing the visual and narrative elements of 8½ and the stage version of Nine, it will ask why Rob Marshall did not manage to re-generate the powerful impact and subsequent commercial success achieved by his previous musical film, Chicago. By contrast to the critical reception afforded to 8½, responses to Marshall's film version towards the end of 2009 were lukewarm. As a film musical Marshall's 2009 movie Nine can boast not only a remarkably complex process of development, but also a profoundly polarised reception. In Nine Marshall attempts to invert the predictable fusion of the heterogeneous worlds of film and 'life' and leaves people in a less comfortable place.