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For your consideration, My Boss's Daughter. This one may be too awful... but it might make a great HDTGM episode. I saw this "romantic"-"comedy" on a date in high school, and we absolutely hated it. It is completely delirious. Ashton Kutcher plays a nice guy seeking his big career break while working under a tyrannical boss (Terence Stamp) at a publishing company. He's also interested in the bosses daughter (Tara Reid). Ashton gets his chance to impress his boss and Tara when he offers to house-sit the boss's manor for a night. Naturally a series of completely unbelievable coincidences, misunderstandings and random events (such as the boss's pet owl escaping and consuming toilet water laced with drugs) leave Ashton struggling to hide from the oblivious Tara what a disaster the night has become. Not a single character really comes of as human or relate-able. In the vein of "I Now Pronounce You Chuck and Larry" there is a scene where Tara feels safe performing a striptease for Ashton because she believes he is gay. (Has that ever happened?) I think delirious is the best way to describe it as there is so much crazy happening and all the characters just roll with it. Its gross; its potentially offensive. There are a few supporting actors who struggle though this film as well. Andy Richtor arrives as Tara's delinquent brother on the run from drug dealers and at one point shows his bare ass. Carmen Electra shows up in a wet t-shirt. I think Keenan from "Keenan and Kel" attempts suicide, if I recall correctly. Molly Shannon as the butt of a joke making fun of spousal abuse. Don't worry, there's room for jokes targeting the handicapped and mentally ill as well. It did awful in theaters and was almost universally hated by critics (for whom the film was not screened in advance). Here are a few of the more amusing quotes from top critics found on Rotten Tomatoes.. -"Even after sitting through it you can't swear you've seen it. It vanishes while you watch, like disappearing ink." -"Mr. Kutcher's comic style is a series of disbelieving blinks and flinches that make him look like a newly hatched ostrich still getting acclimated to his long legs and neck." -"With [Kutcher and Reid] as the star-crossed couple, the title of this movie should have been Zero Plus Zero Equals Zero." -"Three year old brain-dead variant of Risky Business" -"Zucker directs this mess like a substitute teacher soldiering through a day's work for a day's pay at a decertified school."
If Tara Reid is 37 and her son is 22 as Scott mentioned, then she was 15 when she has him. Based on real age for Ian Zehring he is 49, making him 27 when his son was born. I'm surprised Jason of all people didn't mention this.