Elf (2003). I'll admit it. I just never got Will Ferrell until I saw elf. He's childish, but in the best way possible. When holiday stress starts to edge out the good stuff, I pop this dvd into the player and get the joy of the season back again.
How the Grinch Stole Christmas (2000) - recommended by Christy Bledsoe as one of her own favorite Holiday films. "This film is a traditional movie of one going from bad to good. It also has a lot of humor!"