The Family Man (2000)
Kate says "I have a really bad feeling about this".
As Kate and Jack are about to get intimate the first time, Wicked Game by Chris Isaak is playing which was made famous by the Nicholas Cage film Wild at Heart
in Luther's hidden DVD collection
DVD and video case are shown.
Subject of a $10,000 question
mentioned in dialogue
title referenced and still shown
A copy of this movie can be see in Kington mind
The Family Man is #10.