11. My Boss's Daughter (2003)
Director: David Zucker
Stars: Ashton Kutcher, Tara Reid, Molly Shannon, Terence Stamp, Andy Richter, Michael Madsen
Lame Love Song: "If I Had A Million Dollars," Barenaked Ladies
Love Conquers: His boss
You'll never guess what this one's about! And, would you believe it, the guy's boss (Stamp) is a total jerk! And the boss's daughter (Reid) has no idea that the employee (Kutcher at his worst/finest) has feelings for her!
There is something special about a film that offers nothing but hackneyed clichés, a film in which you can predict every turn of the plot, even down to the smallest moments. As you watch Kutcher's character deliver an impromptu mammogram to a stranger, you instinctively know that the boss's daughter will walk in mid-feel, suspecting the worst. The only thing you don't know before it happens is when you will simply give up and start begging for death's icy hand to put an end to your suffering.