The male lead was originally written for John Ritter, but his death stopped Peter Bogdanovich from wanting to make it. When Wes Anderson introduced him to Owen Wilson, he liked him so much that he decided to bring the movie back.
Jennifer Aniston was first offered the role of Delta, but after reading the screenplay, she preferred the part of Jane Claremont. She later advised Bodganovich to cast Kathryn Hahn as Delta and also suggested Will Forte to play Joshua Fleet.
Shot in twenty-nine days.
People Magazine reported this film going into pre-production in the mid 1990s, with the title "Squirrels to the Nuts" and featuring Tatum O'Neal in the leading role. Peter Bogdanovich was quoted as saying "This movie is my gift to her."
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