Movies like Kiss Toledo Goodbye

Starring Bruce Willis and Matthew Perry, The Whole Nine Yards revolves around a mild-mannered dentist and his new neighbor, who happens to be a former hitman. The awkward entanglement with the mob will resonate with fans of Kiss Toledo Goodbye.

Analyze This offers a comical take on the mob genre, with a mob boss undergoing therapy to cope with his anxiety. If you enjoyed the blend of humor and crime in Kiss Toledo Goodbye, this film's blend of the Mafia and therapy-driven laughs is a sure bet.

In this Elmore Leonard adaptation, featuring a mobster trying to go straight by entering the movie business, Get Shorty combines crime drama with sharp wit just like Kiss Toledo Goodbye. Fans of quirky mob comedies will find themselves right at home.

The Freshman pairs a young naive college student with a seasoned mobster played by Marlon Brando in a story that involves ridiculous circumstances, creating a humorous dynamic similar to what's seen in Kiss Toledo Goodbye.

With its spoof of gangster films, Johnny Dangerously delivers over-the-top humor that pokes fun at the mob movie genre. If Kiss Toledo Goodbye hit the mark with its crime comedy narrative, this film's zany antics are sure to entertain.

In Married to the Mob, a mob widow finds herself trying to escape the Mafia lifestyle, dragging her into a world of laughs and trouble. If you appreciate the comic criminal elements in Kiss Toledo Goodbye, this one's for you.

Mickey Blue Eyes stars Hugh Grant as an art auctioneer who gets mixed up with his fiancée's Mafia family. The film's humorous take on a fish-out-of-water scenario mirrors the mob ordeal faced in Kiss Toledo Goodbye, making it a perfect follow-up.

A light-hearted crime comedy that has a former mobster entering the Witness Protection Program, My Blue Heaven’s antics with mobster life colliding with suburbia offer the same comic incongruities that fans of Kiss Toledo Goodbye enjoy.