Tom Stansfield (Ashton Kutcher) is a researcher at a publishing house in Chicago but he wants to be creative. He has a crush on Lisa Taylor (Tara Reid) who is the daughter of his domineering boss Jack Taylor (Terence Stamp). Jack fires his secretary Audrey Bennett (Molly Shannon) blaming it on Tom. Lisa is housesitting for her dad but she wants to go to a party. Lisa asks Tom to housesit so that she can attend her party. Tom assumes that it's a date. Jack has crazy requirements for his owl. Then the irresponsible brother Red (Andy Richter) returns hiding from drug dealer T.J. (Michael Madsen). Audrey comes by to ask for her job back but she brings her annoying boyfriend Spike (Tyler Labine). Spike drives off and Tom reluctantly lets Audrey stay. Lisa's boyfriend Hans cheated on her and she comes home early.Everybody is annoying in this movie and Ashton Kutcher is the welcome mat for them to walk all over on. The screwball slapstick is annoying. Everything and everyone annoyed me in this movie. This is a David Zucker film but it needs to get the characters right before the slapstick comedy could actually work.

It was just last week when I watched "Just Married", which I didn't think was very funny, and now I've also seen "My Boss's Daughter", another romantic comedy starring Ashton Kutcher, which was released later the same year as the other one. I first came across the title of this one a little while earlier, since it was directed by David Zucker. I've seen a bunch of comedies which he was heavily involved in the making of, and have found several of them funny, unsurprisingly including "Airplane!" and "The Naked Gun: From the Files of Police Squad!" However, this 2003 comedy, directed by Zucker and written by David Dorfman, certainly misses the mark, and as a romantic comedy starring Kutcher, it's even weaker than the overall mediocre "Just Married"! Tom Stansfield works for a publishing company as a researcher. He believes he should be part of this company's creative department instead, but his boss, Jack Taylor, is so overbearing that the young researcher is too intimidated to talk to him about his ideas. Tom also has a crush on Jack's daughter, Lisa. One day at work, she approaches Tom and tells him about a party she wants to attend, but her father is making her housesit on the night this party is happening. Tom encourages her to stand up to Jack and go to this party, and she invites the young man to come over to the Taylor mansion that night. He arrives thinking she has invited him to the party, but she's not there when he arrives, and it turns out that she just wanted him to take her place as the housesitter for the night. So, Jack leaves Tom to look after the house, but as the housesitter tries to make sure that nothing goes wrong, he finds that EVERYTHING goes wrong, with people coming in uninvited, breaking Jack's rules, and trashing the place! The humour is basically mediocre at the beginning, showing the protagonist on the subway trying to talk to Lisa, with nothing too funny, and that's unfortunately the way it is for most of the film, only it gets worse as it goes along. Now, I'll admit, I couldn't help but smile several times, even laugh a little a couple times, during early scenes with the Jack Taylor character, played by Terence Stamp, including the first conversation we see between him and Tom, though I didn't find the "retard" part very amusing. Stamp does an impressive job delivering some fairly funny lines, and his performance is the only one here I can really praise. After Tom is left alone at the Taylor mansion, it isn't funny as various people come in and make a mess, which Tom REALLY doesn't want to happen, and the romance between Tom and Lisa is also pretty cheesy. This housesitting session isn't funny to begin with, but the gags get worse. There certainly are some notably lame and juvenile gags, including the urination ones, and I can't forget the Julie character. Her severe head wound is meant to be a joke, but it's not funny at all. The lamest part of the entire film is probably her leaving blood on everything the back of her head touches! Many viewers might think that this juvenile 2003 romantic comedy is horrendous all around, but I can't usually describe a film like that, and this one is no exception. However, I've made it clear that I still don't think it's very funny, and I'm certainly not puzzled at all by the film's bad reputation. As a flick directed by David Zucker, it marked a low point in his career, and apparently, this is the only movie that David Dorfman wrote, other than "Anger Management", which was made shortly before this film. While his other comedy, co-starring Adam Sandler and Jack Nicholson, can be lame in places, it sure is funnier than this dreck! My vote for "My Boss's Daughter" is four stars out of ten, even if it looked more like five stars around the beginning. If it weren't for Terence Stamp's performance here, with the actor still showing his talent despite the film's poor quality, my vote would probably be one star lower.

This film made me so angry because of its stupidity that I felt the need to create an account on IMDb to share with you my opinion. I liked Ashton Kutcher in "A lot like love" and this is why I still wanted to see this film despite it's current 4.2 rating. It is highly over-rated. I trusted that an actor (any of them) would judge the script and would not agree to participate in such low/now quality production. It is very disappointing. The theme of home-sitting was much better used in "Deuce Bigalow: Male Gigolo". Things that did not make sense here: fist of all, the house owner leaves his precious pet with somebody who doesn't know anything about taking care of it. Secondly, the rule is not to let anybody in the house, but the house-sitter fails to follow this simple rule. The door is not locked?! And so on..

This is by far the most awful movie I have ever watched. I have never before rated a movie 1 out of 10. My advice is don't watch it. This doesn't even classify as a movie.You'd be better off sitting on the couch bored rather than watching this movie. Acting was terrible but what was worst by far was the storyline. Highly unlikely sequence of events which aren't even funny. They are actually very lame and stupid. Very foolish choice by Ashton Kutcher and Tara Reid to act in this movie. Might even upset their careers a little.When I walked into Blockbuster, the main focus was on this movie , so I decided rent it. I sincerely regret it.Once you're 10 or 20 minutes into the movie you could basically predict what was going to happen. I was hoping it would get better , but instead it got worse.I am not exaggerating this. The movie is terrible. Don't watch it. Hope this helps.