A man makes some unexpected (and potentially dangerous) discoveries about his family in this comedy. Kevin Gower (Michael Rapaport) is an investment advisor who is engaged to marry the woman he loves, Deeann (Christine Taylor). One day, Kevin is approached by a gruff stranger named Max (Christopher Walken), who "escorts" Kevin into a car. Soon Kevin is introduced to Sal (Robert Forster), a leading organized crime figure who informs Kevin that's he is his biological father. This is puzzling news for Kevin, especially after Sal's limousine is blown up only a few moments later. Madge (Nancy Allen), Kevin's mom, confirms that Sal was indeed Kevin's father, though she thought it best that he not know about it. A few days later, Max and Wendy (Jamie Anderson), Sal's girlfriend, approach Kevin and ask him to attend Sal's funeral. Kevin agrees, but he soon learns that his presence is requested not just to memorialize the life of a friend or relative -- whoever killed Sal may well be coming after Kevin next, and if they can use him as bait, they have a better chance of finding out who rubbed out Sal. Kevin isn't sure how he feels about this, since Deeann is suspicious of Kevin's stories about wiseguys, exploding limos, and Wendy -- and Kevin's co-workers have been wondering where he's been. ~ Mark Deming, All Movie Guide

"An unfortunate film that premiered on cable, it's easy to see why Kiss Toledo Goodbye never made it into the theaters. For starters, it's virtually the same movie as the far funnier Mickey Blue Eyes, with the hapless Kevin (Rapaport) getting inexplicably sucked into the mob lifestyle thanks to the demise of mob boss Sal Fortuna (Forster). While Christopher Walken is always a great addition to any mobster flick, Rapaport frankly looks too much like he belongs in the mafia. Hugh Grant? A much bettercasting call. Too much of Toledo revolves around gunplay, with one shootout after another trying to stand in for plot development. In a word: Boring" (FilmCritic.com)
Walken plays these oddball funny roles soo well, he makes the film very good when without his comic spark it might have been merely standard.....

plot   Trailer
 

Trivia:
Walken has played three different characters with the name Max
(Kiss Toledo Goodbye, Batman Returns and A View to a Kill)