I Was a Teenage Faust (2002)

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.