Highway of Heartache

A would-be country singer (Barbara Chamberlin) falls victim to an abusive mother, the Ku Klux Klan and life itself.

Highway of Heartache is a 1996 feature film that was billed as the first Canadian country-western drag queen musical. Written and directed by Gregory Wild, the film follows the misadventures of Wynona-Sue Turnpike (Barbara Chamberlin, who also write 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. 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.

Highway of Heartache was made in 1994 and had its theatrical premiere in New York in August 1996 at the Lower East Side (116 Suffolk Street) Lighthouse Cinema. Critical reaction was mixed: Stephen Holden in the New York Times complained of a “gratingly hysterical pitch [that] makes a John Waters romp look like a Merchant-Ivory reverie…what began as a screaming Day-Glo comedy turns into a sensory endurance test.� However, Ken Eisner of Variety dubbed it “the weirdest feature yet to come out of Canada� and “consistently funny� and Sandra Brennan in Allmovie stated the “weird and funny Canadian film has all the makings of a cult classic.�