27. Beauty and the Briefcase (2010)
Director: Gil Junger
Stars: Hillary Duff, Jaime Pressly, Jennifer Coolidge, Matt Dallas
Lame Love Song: "Prism of Love," Sly Silver & Sir Realist
Love Conquers: Corporate America
In Beauty and the Briefcase, Hillary Duff goes deep undercover for Cosmo to see what it's like to date a businessman. Now, remember, this was before Mad Men, so you couldn't just turn on the TV and see how wonderful a relationship with a corporate titan could be for a hot woman.
Duff's character's assignment is to "seek out a corporate job, and commence dating as many of her co-workers as possible"â€”because, you know, that's what a woman should use a corporate job opportunity to do. The similarities to Mad Men end there, unfortunately, as HIllary Duff fails to get into any drunken fist fights. It's too bad, because we would be all about that film, though we suspect such a film wouldn't be deemed "on-brand" for ABC Family.