44. Employee of the Month (2006)
Director: Greg Coolidge
Stars: Dane Cook, Jessica Simpson, Dax Shepard
Lame Love Song: "Can't Fight This Feeling," REO Speedwagon
Love Conquers: Working for a warehouse club chain
What Hollywood executive found Dane Cook and his trademark "shocker" gesture so charming that they thought that he would make a great leading man in a movie about employees at a fake Costco chain competing for the affections of a lady cashier? Unfortunately for Mr. Cook, and the sorry son a bitch who made a bet on him, while you can steal jokes, you can't steal dramatic talent.
To be fair, pairing him with co-star Jessica Simpson didn't help matters, as her only previous acting experience consisted of a guest spot on the Twightlight Zone reboot, Dukes of Hazzard, and playing herself in a reality show.