Mr. Inappropriate

Log line: On the eve of his thirtieth birthday, a directionless young man gets an ultimatum from his rich parents: “get a job and a wife or you’re out of the will.” So Mr. Inappropriate goes out looking for an inappropriate wife and an inappropriate job.


Mr. Inappropriate is a comedy about a rich kid with too much time and way too much money. Jonathan Chesney is “Mr. Inappropriate.” He’s the class clown twelve years out of high school on the eve of his thirtieth birthday. His life revolves around a series of pranks and inappropriate skits which he pulls on anyone he deems “appropriate.” Finally, his parents have had enough and they give him an ultimatum: “get a job and a wife, before your thirtieth birthday, or you’re out of the will.”

Jon laughs at their ultimatum and goes on an inappropriate rampage. Sure, he finds a job– working on the set of an adult film. And he finds a girlfriend, too– one of the actresses in the adult film. To his parents horror, he even brings her home to a family dinner. “Enough!” his parents warn him, and they send him out on a series of blind dates with “appropriate” girls, and job interviews for “appropriate” jobs. But not to worry, blowing job interviews and getting “appropriate” women to think he’s thoroughly disgusting is an easy day at the office for Jon.

As Jon’s thirtieth birthday grows closer he does fall in love, but she’s “inappropriate” in his parents’ eyes. By now Jon’s learned a valuable lesson and matured; he decides to get a (inappropriate) job, forsake his parents inheritance, and be with the one woman he really loves, no matter how “inappropriate” she may be.

Inappropriate—yes, politically correct, no. Mr. Inappropriate is a broad comedy with an edge, as it makes fun of all the stuffy, superficial, bourgeois values that run rampant in so many upper class families. It’s a modern day blending of The Graduate with the broad comedy of Liar Liar, with an inappropriate twist.

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