Employee of the Month (2007)

Synopsis: For years, Zack Bradley (Dane Cook) has worked hard at not working hard at all, coasting under the radar as an ambitiously invisible box-boy at the local Super Club. Living with his grandmother, and spending his free time with his box-boy crew, Zack keeps people's expectations of him as low as his profile. So when his kiss-up coworker Vince (Dax Shepard) earns the Employee of the Month title for the 17th time in a row, Zack couldn't care less. But when sexy cashier Amy (Jessica Simpson) joins the store's staff, and rumors being circulating that she only dates winners of this award, the stakes are instantly raised. What begins as a plan to win Amy's heart slowly morphs into a much greater challenge, with Zack's low aspirations gradually growing into earnest attempts at excellence. With the crazed Vince always in his way, Zack must prove his worth to his superiors, his friends, Amy, and himself.     Source: RottenTomatoes.com