My Boss's Daughter (2003)

You can almost guess from the title what My Boss's Daughter (2003) is about. And once you find out that Ashton Kutcher plays the lead, you can bet that some hilarious idiocy will be involved--he hadn't quite been transformed by Demi Moore yet, after all. Kutcher agrees to housesit for his boss in hopes of earning his favor and possibly savoring the flavor of his delicious daughter, played by Tara Reid. When hyped-up house guests such as his boss’s drug-addled on-the-run son Andy Richter, scorned ex-secretary Molly Shannon, and a screeching beastly bird make things difficult, Ashton scrambles to still give the girl a whirl without pissing off her pop and ending up unemployed.