- Hostility on the Set: It was reported that Vince Vaughn and Reese Witherspoon didn't get along. They clashed over differing working methods - she wanted to practice and prepare before a scene, while he preferred to jump right in and ad-lib. Tellingly, they didn't walk the red carpet together.
- Real-Life Relative: Vince Vaughn's father Vernon makes a cameo as a churchgoer during the Christmas play. He is sitting right behind Reese Witherspoon.
- Scully Box: A case that is downright ascended in the film's poster, showing how many gift boxes are necessary to make the diminutive Reese Witherspoon and the enormous Vince Vaughn the same height.
- Star-Derailing Role: Reese Witherspoon saw her career prospects decline when this film was critically panned, along with the political drama Rendition becoming a Box Office Bomb the year before. The two films' failures combined quenched most of the hype she got with her Oscar-winning role in Walk the Line, which she wouldn't recover from until she accomplished a Career Resurrection with Wild. Vince Vaughn's career began to decline too, with the failure of The Dilemma setting it in stone.
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