Kiss Toledo Goodbye is a 1999

1999 in film

The year 1999 in film involved several noteworthy events and has been called "The Year That Changed Movies". Several significant feature films, including Stanley Kubrick's final film Eyes Wide Shut, Pedro Almodóvar's first Oscar-winning film All About My Mother, science fiction The Matrix, Deep...

 independent

Independent film

An independent film, or indie film, is a professional film production resulting in a feature film that is produced mostly or completely outside of the major film studio system. In addition to being produced and distributed by independent entertainment companies, independent films are also produced...

 comedy

Comedy film

Comedy film is a genre of film in which the main emphasis is on humour. They are designed to elicit laughter from the audience. Comedies are mostly light-hearted dramas and are made to amuse and entertain the audiences...

/thriller film

Film

A film, also called a movie or motion picture, is a series of still or moving images. It is produced by recording photographic images with cameras, or by creating images using animation techniques or visual effects...

 directed by Lyndon Chubbuck. Film stars Michael Rapaport

Michael Rapaport

Michael David Rapaport is an American, actor, director and a comedian. He has acted in more than forty films since the early 1990s...

, Christopher Walken

Christopher Walken

Christopher Walken is an American stage and screen actor. He has appeared in more than 100 movies and television shows, including Joe Dirt, Annie Hall, The Deer Hunter, The Prophecy trilogy, The Dogs of War, Sleepy Hollow, Brainstorm, The Dead Zone, A View to a Kill, At Close Range, King of New...

, Robert Forster

Robert Forster

Robert Forster is an American actor, best known for his roles as John Cassellis in Haskell Wexler's Medium Cool, and as Max Cherry in Quentin Tarantino's Jackie Brown, the latter of which gained him an Academy Award nomination for Best Supporting Actor.- Early life :Forster was born Robert Wallace...

, Nancy Allen

Nancy Allen (actress)

Nancy Anne Allen is a Golden Globe nominated American actress and cancer activist.Allen began an acting and modelling career as a child, and from the mid-1970s appeared in small film roles, most notably the anchor of Robert Zemeckis's ensemble comedy I Wanna Hold Your Hand...

 and Christine Taylor

Christine Taylor

Christine Taylor-Stiller is an American actress.- Early life :Taylor was born in Allentown, Pennsylvania, the daughter of Joan, a homemaker, and Skip Taylor, an owner of a security company. She grew up in neighboring Wescosville, Pennsylvania...

.

A young man Michael Rapaport

Michael Rapaport

Michael David Rapaport is an American, actor, director and a comedian. He has acted in more than forty films since the early 1990s...

 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.

Plot

To prevent a gang war, a young Ohio investment advisor Michael Rapaport

Michael Rapaport

Michael David Rapaport is an American, actor, director and a comedian. He has acted in more than forty films since the early 1990s...

 must impersonate a Mafia Godfather for a few weeks following the assassination of his crime-boss biological father Robert Forster

Robert Forster

Robert Forster is an American actor, best known for his roles as John Cassellis in Haskell Wexler's Medium Cool, and as Max Cherry in Quentin Tarantino's Jackie Brown, the latter of which gained him an Academy Award nomination for Best Supporting Actor.- Early life :Forster was born Robert Wallace...

 whom he had not even known existed. He tries to keep this new life secret from his real family, especially from his very jealous fiancee Christine Taylor

Christine Taylor

Christine Taylor-Stiller is an American actress.- Early life :Taylor was born in Allentown, Pennsylvania, the daughter of Joan, a homemaker, and Skip Taylor, an owner of a security company. She grew up in neighboring Wescosville, Pennsylvania...

, with the help of his new Cosa Nostra "family," especially his father's chief lieutenant Christopher Walken

Christopher Walken

Christopher Walken is an American stage and screen actor. He has appeared in more than 100 movies and television shows, including Joe Dirt, Annie Hall, The Deer Hunter, The Prophecy trilogy, The Dogs of War, Sleepy Hollow, Brainstorm, The Dead Zone, A View to a Kill, At Close Range, King of New...