Highway of Heartache (1996)

Written and directed by Gregory Wild, the film follows the misadventures of Wynona-Sue Turnpike (Barbara Chamberlin, who also wrote the film’s score) on a raucous and unlikely road to Nashville superstardom. Backed up by a pair of transvestite guardian angels (played by The Big Wigs), Wynona-Sue faces a variety of indignities including an abusive husband, the threat of life imprisonment and venereal disease.