Wagons East! (1994)

When a group of dissatisfied settlers decides they've had enough of the Wild West, they hire James Harlow, an alcoholic wagon master, to take them back East. The eclectic but happy bunch includes Dr. Phil, prostitute Belle and openly gay man Julian. But the railroad investors don't want it getting out that the West isn't a nice place, so they do everything they can to make sure the group never makes it to their destination.