Chris Farley plays Thomas 'Tommy' Callahan III, a loveable but clumsy heir trying to prove himself.
David Spade portrays Richard Hayden, Tommy's cynical stepbrother and coworker.
Brian Dennehy appears as Thomas 'Big Tom' Callahan, Tommy's late father and founder of Callahan Auto.
Bo Derek plays Beverly Barish, aka Beverly Burns, Big Tom's wife and Tommy's stepmother.
Dan Aykroyd portrays Ray Zalinsky, a successful auto parts manufacturer who helps Tommy and Richard.
Julie Warner appears as Michelle Brock, Tommy's love interest and coworker at Callahan Auto.
Sean McCann plays Frank Rittenhauer, an executive at Callahan Auto who has his doubts about Tommy.
Zach Grenier appears as Ted Reilly, another executive at Callahan Auto who is skeptical of Tommy's abilities.
Robert K. Weiss portrays the 'No' Manager, a character who appears in a humorous scene at a restaurant.
Corey Sevier plays the Boy in Commercial, a minor role in a commercial that Tommy watches.
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