Originally, director John Dahl wanted Dennis Hopper to play Wayne Brown, but he insisted on playing Lyle from Dallas. Hopper eventually convinced the producers who were thrilled with the result.
Nicolas Cage largely took the part due to the recommendation of his uncle, Francis Ford Coppola who is an outspoken fan of John Dahl's first film, Kill Me Again (1989).
John Dahl named Dennis Hopper's character "Lyle from Dallas" after the director's first guitar, a Lyle guitar.
Before Nicolas Cage had been cast, Dennis Hopper suggested that John Dahl should consider Kris Kristofferson, a good friend of Hopper's from The Last Movie (1971), for the leading role. Kristofferson was at a low point in his career at the time, mainly appearing as the lead in made-for-TV movies. He had a packed schedule and declined without reading the script.
Dwight Yoakam brought his own pistol for his role as the Truck Driver. His hit single, A Thousand Miles From Nowhere, is used during the film's closing credits - the version used is a studio demo recording unlike the one from his This Time album.