After the 1860s Wild West, a group of misfit settlers including an ex-doctor Phil Taylor (Lewis), a prostitute Belle (Ellen Greene), and homosexual bookseller Julian (John C. McGinley) decide they cannot live in their current situation in the west so they hire a grizzled alcoholic wagon master by the name of James Harlow (Candy) to take them on a journey back to their hometowns in the East. This leads to a comedy of errors when the drunken wagonmaster leads them into Sioux territory and they are pursued by the cavalry. They also have to contend with hired gunslingers who have been sent by railroad magnates to stop the journey in fear of bad publicity of the west, and their discovery that Harlow had been part of the infamous Donner Party.

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