Kiss Toledo Goodbye is a 1999 independent comedy/thriller film directed by Lyndon Chubbuck. It stars Michael Rapaport, Christopher Walken, Robert Forster, Nancy Allen and Christine Taylor. Rapaport plays a young man who suddenly learns that the biological father he knew nothing about is a crime lord. Upon witnessing his father's death, he is expected to join forces with his new "family" and is challenged to prove himself.
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Plot
Following the assassination of his crime boss's biological father (Robert Forster), whom he had not even known existed, a young Ohio investment advisor (Michael Rapaport) must impersonate a Mafia Godfather for a few weeks to prevent a gang war.
He tries to keep this new life secret from his real family, especially his very jealous fiancée (Christine Taylor), with the help of his new "family" and his father's chief lieutenant (Christopher Walken). At the same time, he is being pressured by his boss at work to sign off on a due diligence report for a questionable investment, trying to keep his family safe, dodging assassination attempts, and trying to uncover who killed his father.
Cast
Michael Rapaport as Kevin Gower
Christopher Walken as Max
Robert Forster as Sal Fortuna
Christine Taylor as Deeann Emory
Jamie Anderson as Wendy
Nancy Allen as Madge
Paul Schulze as Nicky
Paul Ben-Victor as Vince
Saul Stein as Anthony
Robert Pine as Oz
Robert Alan Beuth as Harry
Reception
Nathan Rabin wrote in The A.V. Club, "A ham-fisted comedy that plays like a series of sewn-together outtakes from superior films... Chubbuck presides over Kiss Toledo Goodbye with a leaden comic touch appropriate to his experience directing Baywatch, while displaying all the visual style of a first-time director of amateur porn."