John Cusack plays David Shayne, an idealistic young playwright, newly arrived on Broadway in the roaring 1920s. David stands firm against compromising his work, but soon changes his tune when his producer finds backing to mount his show on Broadway. The only catch is that the backer is a local mobster who sees David’s play as a vehicle for his demanding and talentless girlfriend Olive (Jennifer Tilly). David also has to deal with the demands of veteran theatre diva Helen Sinclair (Dianne Wiest) and is shocked to discover that Olive's hitman bodyguard, Cheech (Chazz Palminteri), is probably a better playwright than he is, as he secretly revises David's work when he sits in on rehearsals. As the players prepare for opening night, David soon realises he is in way over his head.