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 (Joe Viterelli) : a Broadway debut with the chance to direct, as long as Nick's flibbertigibbet girlfriend, Olive (Jennifer Tilly), plays one of the lead roles. As Olive and star Helen Sinclair (Dianne Wiest) attempt to upstage each other, Olive's gangland bodyguard Cheech (Chazz Palminteri) starts suggesting changes to David's script.