Struggling 1920s playwright David Shayne (John Cusack), having failed to secure financing for his latest work, reluctantly makes a deal with mob boss Nick Valenti: a Broadway debut, with the chance to direct, as long as Nick's flibbertigibbet girlfriend Olive plays one of the lead roles. As Olive and star Helen Sinclair attempt to upstage one another, Olive's gangland bodyguard Cheech starts suggesting changes to David's script. Dianne Wiest won an Oscar for her role as Helen Sinclair. The film was nominated for another 4 Oscars at the 1995 Academy Awards including Best Director for Woody Allen.