Kiss Toledo Goodbye

Kiss Toledo Goodbye is a 1999 independent comedy/thriller film directed by Lyndon Chubbuck. Film 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.

Following the assassination of his crime-boss 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.