My Boss's Daughter 2003

Tom Stansfield, played by Ashton Kutcher, is a dedicated researcher at a publishing firm, toiling under the authoritarian rule of Terence Stamp as Jack Taylor. Despite his strong desire to express his creative side, Tom’s talents remain unrecognized by Jack, who is more interested in maintaining control. The only ally Tom has in this hostile work environment is Jon Abrahams as Paul, his sole friend.

Renowned for his calm demeanor, Tom has never displayed anger—until a fateful meeting with Jack leads to disastrous consequences. During a seemingly innocuous conversation about coffee, Jack misinterprets Tom’s comment about a company’s strength being tied to its weakest link, resulting in the termination of Jack’s secretary, Audrey, portrayed by Molly Shannon. This incident unjustly makes Tom appear responsible for her job loss, straining his conscience.

Tom harbors feelings for Jack’s daughter, Lisa, played by Tara Reid, who faces her own battles against her overbearing father. When she confides in Tom about her agitation regarding house-sitting for her father’s pet bird while wishing to attend a party, Tom encourages her to assert her independence by going to the party. With Jack away for a few days on business, Lisa invites Tom over, leading him to believe he’s been invited to the celebration. However, her real intention is to ask Tom to look after her pet owl, OJ.

As Tom arrives at the Taylor home, he discovers that Lisa is already gone, leaving him in the care of Jack’s instructions regarding OJ. This includes keeping OJ hydrated, administering medication—one of which is quite peculiar—and always wearing protective shoe covers. A chaotic night unfolds, beginning with the unexpected arrival of Lisa’s older brother, Red, played by Andy Richter, who is evading drug dealers. Under the pretense of seeking a TV guide, Red’s reckless actions lead to a series of comical blunders as he flushes drugs down the toilet.

Tom’s duties become increasingly complicated when OJ, who has been lethargic due to depression, accidentally ingests the contaminated toilet water and escapes. A frantic search for OJ ensues, and Tom’s misadventures escalate dramatically. An encounter with a suspicious old neighbor further complicates matters, revealing how absurd the situation has become.

Adding to the chaos is Audrey, who arrives in an attempt to reclaim her job, along with her boyfriend Spike. A comedic mishap occurs when she inadvertently damages Jack’s kitchen while celebrating with friends, adding to the mayhem. Meanwhile, Lisa returns home only to find Tom in increasingly compromising situations, leading her to mistakenly think he is gay, a misunderstanding he later clears up.

As tensions peak, drug dealer T.J., played by Michael Madsen, finds out about the mishandled drugs and threatens Tom, adding urgency to the situation. After a series of unpredictable events, including an unintended burial of T.J., things take another turn when Tom and Red must intervene to save Lisa from T.J.’s looming threat.

In a wild climax that includes Tom losing control of a car thanks to a rogue owl, the police arrive, unraveling the web of confusion. Jack, furious over the chaos, initially ostracizes Tom but eventually sees the error of his ways. After gaining perspective from Red, who encourages Lisa to stand up against their father, Jack offers Tom a long-overdue promotion in the creative department.

In a twist of fate, the company flourishes under new leadership, with Hans accompanying Jack to Thailand to enhance operations. Meanwhile, Audrey finds her footing at a coffee shop, and Lisa takes charge of restructuring the company. As for OJ, he’s discovered to have developed a taste for beer, leaving Tom to reflect on the series of hilariously chaotic events that have unfolded.