15 year old Brendan Willy hates himself for being un-cool when he falls in love with the girl of his dreams. Enter Mr. Five, a no good tempter from hell, which in his last attempt to ensnare a soul before being fried for eternity, transforms Brendan into the coolest kid in Indiana, only to find out that this contract isn't going to be easy at all.

A wealthy executive, Drew Latham (Ben Affleck) has no close relationships and becomes nostalgic for his childhood home as Christmas approaches. When he visits the house and finds another family living there, he offers the residents, Tom Valco (James Gandolfini) and his wife, Christine (Catherine O'Hara), a large sum of money to pretend they are his parents. Soon Drew tests the couple's patience, and, when their daughter, Alicia (Christina Applegate), arrives, things get increasingly tense.

A high school senior drives cross-country with his best friends to hook up with a babe he met online.