Just like its predecessor (SirCooly's Groundhog Hunt), this film was delayed. The reason for the delay was the cast and crew's focus on finishing Groundhog Hunt before shooting Luckiest Holiday. When production of Groundhog Hunt was finished, the cast and crew immediately started production on Luckiest Holiday.
The original idea was that SirCooly was going to try to catch a leprechaun, and said leprechaun was going to look and sound like former U.S. President George W. Bush. The idea then later changed to that of the President giving SirCooly advice.
The idea of having former President Bush as a character came from Joe Davis (Christina Barton's brother) who did a spot on impression that was so good that Schmidt couldn't stop laughing. Both Barton and Schmidt both agreed on having the character since former President Bush had a great sense of humor, and may like the film if he watched it.
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