My Boss's Daughter (2003)

There are some things you just don't do.

For today’s feature, we are watching a movie that stars a That 70’s Show alum and involves their romantic interest in the daughter of an older person at their job. Since this is Stale Popcorn and not some publication about successful, critically adored movies, no this is not In Good Company with Topher Grace. That movie was a hit with the critics and at the box office and has like over an 80% on Rotten Tomatoes and this one has 1/10 of its score and did just like okay at the box office despite featuring arguably (at the time at least) the most popular That 70’s Show actor. Glad we got that out of the way.

What are we watching today? My Boss’s Daughter, the Ashton Kutcher vehicle where he uhh falls for his boss’s daughter. What else can I say about it? I don’t remember this one but I feel like I’ve seen it before. Regardless, it has an 8% on Rotten Tomatoes and barely made its budget back, despite Ashton’s star power at the time with Punk’d and Tara Reid’s movie popularity and sex symbol status. These are factors that usually put asses in the seats but that was not the case here. Let’s see why.

Our movie begins with a voiceover from Tom Stansfield (Ashton Kutcher) about his job and how he deserves a creative role at this company and optimism about achieving. He’s on his daily subway commute with his friend Paul (Jon Abrahams) when a man loses his briefcase in the subway door before the man misses the train. Paul tells Tom to take it because he needs a new briefcase. Dave Foley is there wearing a bowtie as a coworker named Henderson. Tom discusses how he deserves a raise and Paul and Henderson argue that he never gets angry or asserts himself. Tom has a crush on a woman on the train Lisa (Tara Reid) and goes to sit with her. She recognizes him from the company but when his newly gotten briefcase opens up, a gay porn magazine is inside. This was the height of embarrassment in 2003 apparently. On the walk into the office, he discusses his humiliation with Paul before he is asked to see his boss Mr. Taylor (Terence Stamp) by the secretary Audrey (Molly Shannon). Taylor is busy firing Henderson as Tom goes in to see him. Bummer. It was probably the bowtie. Taylor addresses Tom about rumors he’s going to shoot the office up, which was a joke Henderson and Paul made on the subway which must have been overheard. Henderson apparently threw Tom under the bus and also lied that Tom made offensive comments about little people. Taylor then asks Tom about his trying to schedule a meeting and has him show his ideas. Tom makes a comment about how bitter the coffee is, leading Taylor to bring Audrey in and abusively criticizes her for her coffee while also using the R-slur heavily. He then asks Tom if his conduct was out of line and Tom regurgitates some corporate jargon bullshit that ends up getting Audrey fired. Taylor credits Tom for the decision and tells Tom to schedule an appointment regarding his ideas with his new secretary, whoever that may be.

Lisa finds Tom in the hallway and tries to talk to him about a conundrum she has where she wants to go to a party but her dad is making her house sit. Turns out her dad is Taylor. What a shocker. Tom tells her to live her own life and Lisa invites Tom over to the house later saying they won’t be back late. Tom seems to think he’s invited to the party but Lisa actually invited him over to house sit in her place. Hahahahahahaha. Tom greets Taylor at the door and tells him he’s making the right decision about Lisa before Taylor makes Tom wear house slippers because his shoes are dirty. Tom realizes mid-conversation that he’s actually house-sitting while Lisa is at the party and not joining her. I’m cringing more at his poor shirt-tuck than I am at his reaction. Taylor introduces Tom to his pet owl OJ who doesn’t fly anymore and gives instructions on feeding and care. He tells Tom he can leave when Lisa and her boyfriend Hans get home, crushing Tom.

On the phone, Paul tells Tom that he can use this opportunity to impress both of them, which shouldn’t need to be explained to an adult but this is Tom. He watches home movies of Lisa on the beach and is surprised by the arrival of Red (Andy Richter), Lisa’s brother, who came to the house looking for a copy of TV Guide. Red sits down and talks to Tom and asks Tom not to tell Taylor or Lisa that he was at the house. He tells Tom a guy is stopping by to pick up a package of “frozen steaks” that Tom remarks are not cold and asks Tom to give it to the guy when he arrives. Audrey stops by the house to beg for her job back as her boyfriend honks his horn and revs his engine. Audrey comes inside and makes a mess as Tom tries to clean up after her. Meanwhile, Red is trying to flush a package of what appears to be drugs down the toilet but it’s backed up. Audrey’s boyfriend Spike (Tyler Labine) loudly enters the house and gets mud all over, yelling at Audrey as she makes a sandwich with Taylor’s food and drinks his beer. This is going HORRIBLY for Tom! Tom tries to get them to leave and Spike makes an anti-Semitic remark and fights with Audrey about a waitress he supposedly cheated on her with. They get into a physical altercation where Spike hits her and Tom kicks Spike out. Audrey wants to stay with Tom but he tries to get them to mend their problems rather than have her stay there. What a piece of shit.

OJ the owl is making noises upstairs as it needs to drink water. Tom gives it water out of the toilet that Red was flushing drugs down so this can only go poorly. Lisa calls the house to check on Tom and hears OJ squawking, which she remarks he hasn’t done in years. Lisa asks Tom to stay the whole night so she can crash with a friend after the party and he says yes. Tom lets Audrey stay rather than let her go to a homeless shelter. Red is hiding in the house as a guy (Michael Madsen) shows up to get the package Red left with Tom. Tom goes to feed OJ and OJ starts flying which startles Tom, causing him to drop a cage of mice meant for OJ and having them scurry everywhere. OJ begins to fly for the first time in years thanks to the drugs and attacks Tom as he catches a mouse, sending Tom careening off the stairs, breaking the banister on the way down. OJ then flies out of the house as the pizza guy opens the door. Tom is baffled as to how OJ started flying but runs outside to try and find him before he loses his job. Red tells Tom to relax and Tom yells “OJ’s loose! There’s no time to relax!” which scares a passing group of white blonde women. Ugh. Tom chases OJ onto a neighbor’s property and the neighbor Arthur (Patrick Crenshaw) sticks Tom up at gunpoint assuming he’s a peeping Tom looking at his young wife. Tom gets the gun away and Arthur tries to give Tom “Evander Holyfield’s bitten ear” in a bag in exchange for letting him loose as his wife falls off a climbing wall. Tom unloads the gun and goes back to the house, finding some people partying in the kitchen. Speed (David Koechner), Darryl (Ron Selmour) and Tina (Carmen Electra) are making a bigger mess trying to cook and Tom asks Audrey to keep her friends out of the house and Audrey make a racist remark. This fucking movie man. She gets everyone to go outside and Tom is momentarily relieved.

Lisa arrives home and tells Tom she had a fight with Hans. This should be the point where Tom leaves and allows Lisa to handle the problems in the house but he likes Lisa so obviously he’s just gonna hang around. Lisa tells Tom he can stay as Audrey says she needs Tom’s help. She tells Tom they found OJ but he got away again. Spike tries to make a ground beef lure for OJ and tells Tom that Desi Arnaz killed JFK. Tom goes into Lisa’s closet to get a mouse out of his pants and Lisa catches him holding her underwear somehow. He explains and they go chasing the mouse that got loose but end up causing a ruckus. She pours Tom some wine and he sees her signed Walter Payton poster, telling her she’s the coolest girl ever. She shows Tom her charcoal drawings and asks him to pose nude for her sometime for a sketch. He tells her to pursue her art career but she confesses that it doesn’t align with her career plans at the company. They spot the mouse and chase it, but Tom breaks a table in the process. Lisa tells him it’s fine because it belongs to Red and notes that they have a restraining order against Red. He’s not allowed within 100 yards of her, Taylor or the house. She tells Tom about all the trouble Red causes as he hides her from seeing Red with Audrey’s party-goers doing a stunt outside that seems to have been specifically to give the movie a reason to show Carmen Electra stroke her breasts in a wet shirt. I’m all for Carmen Electra in a wet shirt but this just feels like a cheap patch on a lackluster plot.

Tom and Lisa go back inside and talk more, bonding about how much they have in common. Lisa crushes Tom by saying the reason she can talk to him about anything is because she has no sexual attraction to him. The poor sucker. They dance and Tom has that confused Ashton Kutcher look on his face as Lisa does a striptease to a slow song for him. I don’t know why she thinks he’s not sexually attracted to her, but apparently that thought didn’t cross her mind. Oh, there it is. She thinks he’s gay. He tells her he’s not but she says that her father said he was because Tom is feminine. She says it’s fine and Tom asks what Hans did to upset her. She tells him that Hans has done a lot to betray her trust and confesses that she can’t attract a decent guy. I guess we’re supposed to think one is sitting right next to her but Tom actually really sucks. He confesses that the only reason he took this job is because he likes Lisa and then goes to kiss her. He has to run off because he sees Red and Michael Madsen are running through the house. Michael Madsen confronts Tom saying that he sold him flour and pulls a knife. Tom tries to explain that he’s only there housesitting as Michael Madsen ransacks the bedroom before he’s interrupted by a phone call. He tells Tom he’s going to bring Vasquez, his boss, back in an hour for the actual drugs. Tom finds Red and freaks on him, trying to get him to deal with the drug guys and telling him he knows about the restraining order.

Downstairs, Hans (Kenan Thompson) arrives to try and win Lisa back and gets emotional with Tom. Tom tries to lead Hans out of the house to get Lisa to himself because he’s selfish. Hans confesses that Lisa caught him having sex with some other woman at the party and Tom chastises him. Hans apparently just realized that this constitutes cheating and is broken up about it. Tom gets him to leave as OJ flies by and Tom gives chase. OJ lands on a nearby windowsill and enters the house. He’s greeted by an old woman (Charlotte Zucker) who mistakenly thinks Tom is there for a date with her granddaughter Julie. Julie’s disabled uncle George (Jim Byrnes) tells Tom that losing his sight and ability to walk has helped gain large erections but is angry that no women want him. Julie’s father Ken (Jeffery Tambor) enters and Tom tries to clear up why he’s there but can’t get a word in as Ken abusively forces George out of the room and tells Tom that Julie is self-conscious after the accident. Julie (Ever Carradine) enters as Tom tries to explain himself, but Julie assumes it’s about her appearance and runs off crying. Tom still can’t explain because apparently, he can’t speak. Like Jesus, I would have told these people why I was there in the first five seconds. He gets kicked out of the house before getting OJ back.

Audrey tells Tom that Tina thinks she has cancer and asks Tom to feel her breasts and Audrey’s breasts. Obviously, this was just a moronic setup to have Lisa walk in and see this. God this movie fucking blows I can’t wait until it’s over. Lisa comes in and Tom tries to explain and for some reason, Audrey and Tina are completely silent and don’t back him up. This entire movie revolves around the concept that no one can open their fucking mouths to speak. Michael Madsen is back with a crowbar, prying a safe open. Tom pulls the gun he took from the neighbor but Michael Madsen whips his dick out and taunts Tom. He pisses on Tom’s leg and then pisses all over the room. Taylor calls and tells Tom to keep everything in order, saying he may be back early and that they’ll discuss Tom’s career prospects when he returns. Michael Madsen takes Tom’s gun from him, sees it’s empty and gives it back before leaving to get a drink.

Tom goes to the bathroom to wash the piss off him and spots a tube of rectal cream belonging to Taylor. I don’t know why this is important. Audrey interrupts him to give him sleeping pills she got from Speed, telling Tom to slip one to Michael Madsen to get him to stop terrorizing the house. He drops one in the glass of whiskey Michael Madsen is holding, but he has another glass in his other hand and I think Tom drugged his own drink. Michael Madsen gets the safe open but then violently topples over so I guess Tom got the right drink. Michael Madsen is seizing on the floor and Tom calls Audrey in for help. Spike arrives and tells Tom he wasn’t supposed to mix whiskey with the pills, but insists he’ll be fine as Spike used to be a paramedic. Red tells Tom that they think they found OJ when Julie arrives and asks to come inside. Red comes in and introduces himself and Julie tells Tom her real date arrived and also left, vindicating Tom. She tells Tom and Red no guys have ever liked her, except for “a trucker who tried to rape her” my god this movie is awful. Tom keeps trying to prevent Julie from putting her bleeding head wound on the furniture and leaves Red in charge before going to find OJ.

Tom goes outside and finds the partygoers burying Michael Madsen. I guess he died. Tom wants to call the cops but everyone else insists the cops won’t believe them and reminds Tom that he’s the one who put the pill in his drink, therefore Tom’s responsible. He deflects blame to them and Tina asks Spike to say a eulogy for TJ. I guess his character’s name was TJ. Lisa comes outside and finds Tom. She tells Tom that the whole night was a big mistake. Red wanders over to Lisa’s surprise and Lisa asks if Red is the reason OJ is gone. TJ’s hand emerges from the ground. He’s not dead. He grabs Lisa and takes her hostage but Tom knows the gun is unloaded and taunts TJ to shoot her. He throws Lisa aside and points it at Tom. Tom acts tough and whips his dick out, mimicking TJ’s earlier diatribe. As TJ is about to shoot, Red clonks TJ over the head and Tom gets the gun. Lisa tells Tom how brave he was. He tries to tell her the gun was unloaded but it goes off. Spike confesses he reloaded it with the bullets Tom left in the kitchen when he unloaded it in the first place. Darryl then comes outside saying Taylor called and Tom needs to be at the train station in fifteen minutes to get Taylor or he’s fired. Lisa vows to have everything fixed when they get back and tells him to put his dick away.

We get a cleaning montage like this is a college party movie. This shit feels like a low-stakes bad cartoon. I just want OJ to be okay. Spike and Audrey seem to be falling for each other because why not squeeze more nonsense into this shit. Tara Reid really is not the best actress but, in this feature, she’s doing just great. In the car, Tom is driving Taylor home while Taylor is on a call. There is a mouse on Tom’s shoulder and OJ is flying along side the car. Taylor doesn’t seem to notice as Tom starts driving erratically. He also doesn’t notice as the mouse crawls across his back and OJ flies next to the window. Hans enters the house with a duffel bag just as Lisa and Spike finish cleaning. A bunch of cops surround the house looking for TJ, thinking Spike is TJ and try to apprehend him. Spike tries to explain as they all enter the house and find Hans attempting to hang himself from the hallway chandelier, which crashes down breaking. All of the sudden, OJ flies into the car and Tom loses control. Taylor grabs the wheel and makes it look like he’s blowing Tom. The humor in this is even lower-brow than I can stand. Tom and Taylor of course crash the car right into the house. Taylor finds the place in complete disarray and tells Lisa to pack up and go with him to Thailand. Taylor tells Tom to leave but Tom confronts Taylor about some shady business he did in Thailand and shows Taylor the tube of cream from the bathroom. He accuses him of…something and rips his pants down in front of everyone, forcing them to look at Taylor’s ass for signs of folliculitis but there’s nothing there. The cops go to cuff Tom but Red comes out and confesses that he has folliculitis and his ass is red, which is how he got his nickname. He has the same name as his father and the cream is his. He confesses that he was dealing drugs and is the reason TJ was there but tells them he gave TJ flour and flushed the real shit down the toilet, which Tom realizes OJ drank from. OJ flies back in and drinks from the toilet again. Taylor seems this and is overjoyed but OJ flies out of the house and causes a large car crash. We are led to believe OJ is dead and now the only redeeming factor of this movie is out the window, figuratively and literally.

The cops take Tom away and it starts to rain as the camera focuses on a trash bag on a roof that the gang missed. The next morning, OJ is okay. Thank god. He flies back onto the roof and Taylor tries to get him back inside. Red confronts Lisa about actually going to Thailand with their dad. Red says he’s going to bail Tom out of jail because nothing that happened was Tom’s fault. He remarks that Tom was the only guy nice enough to Lisa who also had the balls to stand up to Taylor and tells her the only reason he was there in the first place was to try and spend time with her. He comments that doing everything right gets him put in jail. Taylor overhears this as he’s outside the room on a branch trying to get OJ. Red says that all Taylor cares about is OJ and Lisa confesses she used to wish she was OJ so she’d get Taylor’s love and care. He reaches for OJ but the branch breaks. He grabs a gutter and gets his face covered with mud. OJ rips open the bag on the roof and Taylor gets pelted with empties as he scares his children when he flaps against the window. Red tells Lisa not to leave.

In the airport, Tom catches up with Lisa after Red bails him out. He tells her that everything that happened to him was because he let people walk all over him. Tom tells her she can’t let Taylor control her, but she tells Tom that she’s going to stay as Taylor approaches. She kisses Tom and confirms he’s the reason she’s staying. Taylor and Lisa have made amends and Hans is off to Thailand to take over whatever the hell Taylor was going there to do with some of the other guys in the office. Taylor had found some of Spike’s conspiracy writings in the living room and thinks they’re Tom’s. He tells Tom that outside-the-box thinking like that should give him a better role, so he promotes him to head of the creative department. Henderson then pees on Taylor’s shoes trying to get his job back. Red and Taylor have made up too. Tom gives us a final voiceover. Taylor restructures the company based on his kids’ suggestions. OJ now drinks beer instead of drugged water. Audrey got a job at a café. There is yet another racist joke at Hans’ expense. Tom writes a book about his experience and Lisa does the artwork. Tom laments that people who always say, “why me?” need to look around and see things happen for a reason as Hans finds a briefcase on the ground, and that’s our movie. There might be scenes during the credits as it appears there are, but I am not watching. Nothing consequential could possibly be there and I’ve had enough.

Well, I guess sometimes Rotten Tomatoes really gets it right, huh? I don’t know if I’d give this a full 8%. Maybe a 4% since College has a 5% and this is for sure no College. But there’s a cool owl and a couple okay jokes in the middle of all the racist, homophobic and ableist attempts at jokes. This is one of those movies where if it was just like playing, I might not turn it off. But I would absolutely not seek this one out. Who knows? Maybe you will. I definitely didn’t see this one before as I thought I had, but now I did and one thing I can say about this movie is “I have seen it”. If you want to see how bad this one is for yourself, it’s streaming on HBO Max. Don’t say I didn’t warn ya.