Christmas Do-Over (2006)

A ne'er do well father and ex-husband who always raced his way through the holidays is forced to relive Christmas Day time and again until he gets it right in this family oriented fantasy comedy starring Jay Mohr. It's Christmas time once again, and as usual Kevin (Moore) is scrambling to get his son Ben a last minute gift before stopping by his ex-wife Jill's house for a quick swig of eggnog. Ben can't stand Jill's impossibly perfect new boyfriend, and the prospect of spending the entire evening with his former inlaws is nearly too painful to ponder. But this Christmas things are going to be different, because this Christmas might just last forever. At first Kevin resists the curious development by simply reverting to his childish ways, though he is about to find out that sometimes in order to build a better future one must finally make amends with the past. ~ Jason Buchanan

Source: TMDb