20. Christmas Caper (2007)
Director: David Winkler
Stars: Shannen Doherty, Ty Olsson, Conrad Coats
Shitty Gift Equivalent: Shannen Doherty.
One of our favorite tropes on film is when criminals, who are supposed to have been good at their "job," make stupid mistakes as soon as the film begins. After a con gone bad draws media attention, Cate Dove (Doherty) elects to return to her childhood neighborhood in Connecticut and babysit her niece and nephew while laying low.
While staffers at Complex's NYC offices do everything they can to avoid going to Connecticut, particularly if they have family there, it is by no mean's an out-of-the-way backwater state. ESPN is there for God's sake, as well as...other stuff?
Anyway, we're no crime experts, but don't you usually want to distance yourself from your identity when laying low rather than chilling with family? Also, her childhood town is called Comfort—oh sweet sweet irony. Even with witty banter that produces lines like "I've always wondered it Santa wears boxers or briefs" (Wasn't that gag played out by '92?), not much is done to counter the weakness of the feeble plot.