My Boss’s Daughter Recap


There was a moment where I thought My Boss’s Daughter could be a Grandma’s Boy. A film with terrible reviews that contained a bunch of funny stuff and was actually good. Then I was like, ‘nah, this ain’t that,’ and so I revised my opinion mid-movie and thought perhaps it was a Freddy Got Fingered. An interesting film that was probably actually bad, but also not as bad as the reviewers made it out to be and mostly reviled for its strangeness. But even that wasn’t quite it. Finally, after going through these stages of grief I arrived at the truth: this movie is real bad. That’s right, the film is trash. Don’t get me wrong, there are some funny jokes in there and the supporting cast consists of some of the best in comedy. But it all came down to a simple fact: they had no idea what they wanted to make. And so only about 25% of the film is any good. The rest is appallingly bad.  

To briefly touch on the plot, Tom is in love with his boss’s daughter Lisa. Tom also wants to make it big in publishing but Lisa’s dad is a big ol’ mean face. One day Lisa asks if Tom could help her out and he’s psyched, but less so once he realizes that helping her out means he’s owl-sitting for her father while she goes to a party with her BF. Hilarity ensues as everything, everyone, and every owl goes wrong. Drug deals go bad, Tom is mixed up in a murder most foul, Lisa comes home admits she thought Tom was gay, the owl gets high on cocaine and flies away, etc. etc. etc. Then Lisa’s father gets home early and Tom is fired for acting like a crazy person. But Tom has grown a spine through the ordeal and goes after Lisa, they smooch, and live happily ever after.

So yeah, it’s some real crazy stuff that doesn’t add up to much. It can’t seem to stick to a theme and falls apart under the weight of four different styles. 

  • Director David Zucker. He’s best known for his spoof movies. Indeed, I think the most successful aspects of this film are when they start to border on spoof. An owl is sucking down cocaine and running wild and I swear if they just called it The Great Owl Adventure I would have been into it. 
  • Writer David Dorfman. The writer of the film was hot off making Anger Management and making a splash in Hollywood and his voice seems to contain a bit of acid that works against the lighter, spoofier tones of Zucker. Much of it doesn’t age super well either.
  • Standard Studio Rom Com. It’s already a wild idea to pair this script with that director, but to also then shoehorn in a Tara Reid/Kutcher stereotypical love story in the middle of it? Not a single moment of Kutcher and Reid together works.  
  • Ashton Kutcher Vehicle. Kutcher was clearly on his way up. So when he gets his leading role he is giving it his all in the biggest, broadest way… even when his character reads more like a nervous Woody Allen character than Ashton Kutcher. 

You mix these four things together and it’s a stew not worth eating. When you extract The Great Owl Adventure… now I’m interested. That’s actually my Hot Take Clam Bake. Very simple: more owl=more money. I wanted to sit down thinking, ‘hmmm, just another rom com, sigh.’ Only to then perk up when I realize this isn’t a love story between Kutcher and Reid… it’s a love story between Kutcher and the owl. Fly me to the moon, owl. That hot take it ice cold, baby. Patrick?


‘Ello everyone! My Boss’s Daughter? More like What Dross and Rotter! Amirite? I mean, yeah, if I were British … oh, wait, I am British! Let’s go!

  • There was a time not too long ago when people made unfunny garbage where the “comedy” was all gross-out and the plots all paper-thin. The era I’m sure was great for some people, and perhaps even Dimension Films. It wasn’t great for comedy. This movie is unfunny garbage.
  • Kutcher and Reid are both shockingly bad in this film. I never really thought Kutcher was a particularly good actor. He’s a bit one note, seems to lack a bit of range. But he’s particularly bad in this, presumably as it was quite early in his career (when filmed, I believe the film was shelved for years prior to release). It is actually incredible Tara Reid had a major motion picture career at all. No offense.
  • It was nice I suppose to see Andy Richter bumming around though. He’s actually pretty funny in this. But he’s also a television actor and his part isn’t nearly big enough to save the film overall.
  • Oh there were some funny jokes I suppose, mostly concerning an owl named O.J. (after O.J. Simpson) who causes quite the stir after getting high on cocaine. There is a kernel of something there in that the owl is almost always a terrible puppet/doll that Kutcher interacts with. There is something actually funny about half-assing what is (wildly) the centerpiece to the whole movie: the escape of the antagonist’s pet owl.
  • Oh, and add this to the films where the main character works in book publishing. I … don’t think they know how the book publishing world works. I’m not sure the primary job of a publisher is coming up with ideas for books … I think the authors do that. But what do I know?
  • The film definitely has a nice Product Placement (What?) for both Miller Lite and Cheetos. But other than that I think there are basically no superlatives. The film is closest to Bad, it is unfunny garbage and not interesting in any particular way beyond being a time capsule for everything bad about comedy in 2000.
  • I think I need to name this segment. Jamie likes Live Free or Die Hardcopy (soon to be a smash hit podcast I’m sure). Anyways, plenty of special features on the DVD I got from my local library. We got Bloopies (F, unfunny trash, but hey, so is the movie). We got Deleted Scenes (B, but only because it was a scene that was basically only half done and looked ridiculous). There is a making of Documentary (D, oh boy does it explain why this film is unfunny), and a (gulp) Tara Reid Audition … alright, I’m just going to stop right there for a second. They have Tara Reid get actually half-naked in her audition. Now I’m not one to presume. I’m not one to try and project my thoughts and feelings onto situations. Let’s just say … not a great look. I give the segment a (D, not a great look), and leave it at that.

You best believe I made up a sequel called My Boss’s Granddaughter. Cheerios, and back to you Jamie!


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