Matt Dillon and Richard Jenkins both previously appeared in There's Something About Mary, which shares a similar plot to this film. Both films involve different men all falling for the same woman. Matt Dillon plays one of the men in both films and Jenkins plays a similar role in both films as well. In "Mary" he plays a therapist to whom Ben Stiller tells his story and in this film he plays a priest to whom John Goodman tells his story.
When Jewel talks about when Randy worked as a bartender at McCool's, Jewel says Randy reminds her of a rock star. A nod to Liv Tyler herself. In real life, Liv Tyler is the daughter of Steven Tyler, the lead singer of the hard rock band Aerosmith.
A possible spin-off that focused on Jewel Valentine (Liv Tyler) was never considered due to the death of screenwriter Stan Seidel. If so, a "Jewel Valentine" spin-off film could reveal the femme fatale's origins and detail how Jewel met Utah and became his partner in crime and their other crimes they committed prior to McCool's.
The film has a alternate ending. In the alternate ending, It is Mr. Burmeister whom shoots and kills Elmo and Randy is blamed for the shootout and is arrested by the police. As Randy is dragged away by the police. He sees Jewel get into Mr. Burmeister's car and realizes that the two of them had masterminded everything that has happened. The ending was changed because it didn't too well with test audiences and had found it too depressing.