My Boss's Daughter suffers from a severe case of trying too hard to be funny, which is why it sat on the shelves for over a year before being relegated to the dregs of summer. Ashton Kutcher (Just Married, Texas Rangers) plays a variation of the character he plays a lot, the normal nice guy stuck in abnormal circumstances. In fact, the way that My Boss's Daughter plays out is similar to the way Dude, Where's My Car? unfolded. It's like a big farce, except it's not funny. One thing happens after another, and everything heads towards some huge climax. Here, Kutcher is Tom Stansfield, a peon in research who longs to be in creative, where his true talents lie. His problem is that his megalomaniacal boss, Jack Taylor (Terence Stamp, My Wife is an Actress, Full Frontal) does not know that he exists.

Tom also has a huge crush on Jack's insanely gorgeous daughter Lisa (Tara Reid, Van Wilder, American Pie 2), who also works at their firm. Lisa thinks of Jack as a nice guy who will always do what he's asked, so she asks him to house sit. Tom thinks that he's going on a date, so boy is he surprised when he gets to the Taylor residence! Not. This is the first 'mistake' in a script that snowballs from there. Jack introduces Tom to his pet owl, and gives meticulous instructions on how to care for him, as well as for his pristine house. Tom sees an opportunity and decides to do his best, both to impress Jack and possibly get the job, and to impress Lisa. Of course, everything happens to prevent that.

Jack's secretary Audrey (Molly Shannon, American Splendor, The Santa Clause 2) shows up. Earlier, Tom was inadvertently responsible for firing Audrey, and she wanted to try to get her job back. But, now that Jack is gone for the weekend, she just stays, and even brings some friends over to trash the house. Then, the owl escapes, prompting Tom to begin panicking. Helping him panic further is Jack's estranged son (Andy Richter, Big Trouble, Scary Movie 2) who is participating in some drug deal with TJ (Michael Madsen, Die Another Day, The Real Deal), who shows up to collect. Then, Lisa comes back, as does her estranged boyfriend (Kenan Thompson, Master of Disguise, Big Fat Liar), and random assorted other troubles happen. It's no surprise that the house gets trashed and Jack will come back early. And will Tom win Lisa's heart? Duh.

The problem is that while nobody knows what to expect from David Dorfman's (Anger Management) script, everything that does happen feels contrived. Everything goes wrong, and it's supposed to be funny, but is just tedious. Kutcher has some comedic talent, but a good script would help him out greatly. Everybody else is so one-dimensional that they make no dent whatsoever. Director David Zucker (BASEketball, For Goodness Sake) feels like he is directing a series of barely connected skits instead of a cohesive movie. Tom encounters somebody and something unfunny happens, then he moves on. My Boss's Daughter is pretty stupid all-around, which also explains why the title is misspelled.