Guy Maddin's The Saddest Music in the World, first screened at the 2003 Toronto International Film Festival and released theatrically in 2004, was made in his patented anachronistic style. Shot in grainy black and white with kitschy patches of colour and plenty of gauze, hot with artificial backlighting, it is based on obvious sets that look as if they were appropriated from the German Expressionistic films of the early 1930s.

In the film, Winnipeg has been voted the "World Capital of Sorrow" by The Times of London in the Depression winter of 1933. Local beer baron Lady Port-Huntly (Isabella Rossellini), who has lost both of her legs in a car accident and replaced them with glass prosthetics filled with beer, holds a contest to discover the saddest music in the world. A failing Broadway producer and former lover of the good Lady (Mark McKinney), his nymphomaniac girlfriend (Maria de Medeiros), his drunken father (David Fox) and his absent brother (Ross McMillan) are among the characters seen during the competition. Play-by-play radio broadcasts accompany colour commentary, and the winners celebrate their victory by riding a chute into a giant beer vat.

At times the film, adapted very loosely by Maddin and George Toles from an original screenplay by Kazuo Ishiguro (author of Remains of the Day), appears to be the work of a manic depressive with its frenzied editing, its lack of concentration on anything for more than a few minutes, and its overall downbeat theme. Yet for all its calculated weirdness The Saddest Music in the World has been regarded by many critics as Guy Maddin's most accomplished feature-length film, and it won Genie Awards for best editing, costumes and original music.