Popular country & western singer and well-regarded character actor Dwight Yoakam steps behind the camera for this revisionist Western, his first effort as a director and screenwriter. Valentine Casey (Yoakam) is the sheriff of the town of Los Tragos in the Arizona Territory. Valentine, an orphan, was raised as a child by Leland Henry (Luke Askew), a notorious outlaw, but while Henry's sons Taylor (Vince Vaughn) and Arvid (Paul Reubens) have followed their father into a life of crime, Valentine dedicates himself to putting Henry and his gang behind bars. But when the Henry gang knocks over a bank, Valentine and his posse are hopelessly outnumbered (and intimidated by Leland's Gatling guns). Years later, word has circulated that Valentine died while fighting in the Spanish-American War, but he mysteriously appears in an Arizona border town, winning the affections of a visiting actress named Adalyne (Bridget Fonda) and attracting the wrath of Brigadier Smalls (Billy Bob Thornton), Adalyne's beau and a mysterious figure with a troubling secret. South of Heaven, West of Hell also features supporting performances from Bud Cort, Michael Jeter, and Bo Hopkins. Dwight Yoakam also wrote the film's original score, in collaboration with his longtime producer and sideman Pete Anderson.