Highway of Heartache is a Canadian musical comedy film, directed by Gregory Wild and released in 1994.

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 drag queen guardian angels (played by The Big Wigs), Wynona-Sue faces a variety of indignities including her abusive husband Clive (Serge Houde), the threat of life imprisonment and venereal disease. The film's humor ranged from gross-out to surreal (the heroine's gynecologist was an Elvis Presley imitator), and the entire film was shot on Day-Glo sets designed and built by Wild.

The film received a one-night preview screening in Vancouver, Wild's hometown, at a fundraiser for the Vancouver Meals Society on August 11, 1994, before having its official theatrical premiere at the 1994 Toronto International Film Festival.