In what film does Christopher Walken play a mob boss known only as The Man With The Plan?
Christopher Walken plays a mob boss known only as The Man With The Plan in "Things To Do In Denver When You're Dead" (1995). This is a perversely comic movie about crime and criminals from director Gary Fleder and producer Cary Woods.
In the film, a retired mob fixer, Jimmy "The Saint" Tosnia (Andy Garcia), is a man of action. He was educated in a seminary and has never killed anyone for his sadistic, wheelchair-bound boss, The Man With the Plan. This is, in this instance, something hard to believe. The silver-tongued Jimmy, with impeccable manners to match his suits, is a romantic; he likes to think of himself as a real 'Don Quixote', living in a very sick world. He picks up Dagney (Gabrielle Anwar) at a bar. He tells her that she's a girl who "glides", a free spirit. She is receptive to his clever words.
After Jimmy quits The Man With The Plan, he begins running a video service that allows dying people to make afterlife tapes for their relatives. Business isn't good, so Jimmy agrees to perform one last job for The Man. He is hired to work with The Man's addle-brained, child-molesting son, Bernard (Michael Nicolosi). Besides other things, the two men must stop a guy who is trying to take Bernard's girl from him.
The idea is to scare the guy off. For aid, Jimmy calls in four hard-luck thugs. The idea doesn't work. A murder occurs and The Man hires a notorious hitman Mr. Shhh (Steve Buscemi) for revenge on the thugs. Killing is The Man's answer to end the situation.
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