According to Martin Short (DVD commentary), the film was made in 20 days mostly in Vancouver, BC, with dialog improvised by the actors.
The final film of both Peter Breck and Jan Hooks. For Breck, it was his final on-screen appearance ever.
The film was released shortly after Martin Short's Comedy Central series Primetime Glick (2001) was canceled.
On Primetime Glick (2001), Martin Short's character Jiminy Glick made many references to his four sons: Morgan, Mason, Matthew, and Modine. Glick claimed his latter two sons were twins, and that he intentionally named them after actor Matthew Modine. Landon Hansen and Jake Hoffman portray Matthew and Modine respectively in this film. Morgan and Mason are not depicted.
Martin Short's character Jiminy Glick was inspired by Skip E. Lowe, who hosted a weekly talk show for public access cable television where he frequently interviewed film stars and celebrities. Lowe's show aired in Los Angeles, New York, and other major markets.