 David Shayne (John Cusack), a neurotic playwright, has just found a way to have his play produced. Mob boss Nick Valenti (Joe Viterreli) has faith that the play will bring in big bucks. Nick is a little stubborn, and demands that his wannabe actress girlfriend, bimbo Olive (Jennifer Tilly) have a large part, but Olive is a terrible actress and a conceited moron. Above all that, David is caught in an affair with lead actress Helen Sinclair (Dianne Wiest) and constantly at odds with the cast and crew. Soon he finds himself taking writing tips from Olive s bodyguard Cheech (Chazz Palminteri), who turns out to be a great writer himself. When the cast is introduced to Cheech s rewrite (thinking its David s) David starts getting amazing compliments. Knowing whom the real writer is, David starts to question whether or not he is a true artist.