Larry Bishop, a biker-movie veteran, and Michael Madsen met while working on Quentin Tarantino's Kill Bill: Vol. 2 (2004) and decided to do this movie together.
David Carradine turned down his role at first. Larry Bishop rewrote his part and said he could shoot it in one day. Carradine agreed.
Quentin Tarantino turned down the role of Comanche so that he could act as Ringo in Takashi Miike's Sukiyaki Western Django (2007).