The Saddest Music in the World is the 1930’s expressionist baby of Beerfest and Christopher Guest mockumentaries.

Filmed in grainy black and white that is stylistically cut to resemble a movie made in the depression era, this is actually a fairly impressive piece of media to watch. Picture it – Winnipeg, my ancestral home, 1933. Lady Helen Port-Huntly (who is played by fucking Isabella Rossellini, holy shit), the owner of the Muskeg beer empire, announces a lucrative contest to drum up sales: Whatever country can sing her the saddest music will win twenty-five thousand depression-era dollars. Citizens worldwide flock to Canada to compete, including hometown hero and failed Broadway producer Chester Kent and his self-proclaimed nymphomaniac girlfriend Narcissa, an amnesiac unsure of her country of origin.

Chester’s return to Winnipeg is riddled with its own drama, as his father, a former Canadian soldier, disapproves of his son’s carefree lifestyle in the fast-paced country of America. Also, Chester used to boink Lady Port-Huntly, and his dad was not only obsessed with her, but drunkenly amputated both of her legs after a car accident caused by Helen giving Chester road head. Chester visits the beer tycoon upon his arrival, and they relive this traumatic experience through a dramatic, orchestral retelling that I wish I could link here because it’s probably the most interesting part of this film. Afterward, his father appears to enter his rendition of the aggressively Canadian “Red Maple Leaves”, and Chester proposes their own personal bet. Father vs. Son; Canada vs. America. Lady Port-Huntly is thrilled by the prospect.

After Helen informs Chester he won’t receive any special treatment, he returns to his father’s home and is shortly reunited with his brother, Roderick, who has flown in from Serbia to compete. A hypochondriac who is mourning the death of his son and the dissolution of his marriage, Roderick covers his face in a black veil while he plays dirges on his cello. He listens to one particular ditty, “The Song is You”, every day, but refuses to perform it in the competition because he’s saving it for when him and his wife are reunited. Chester and Roderick’s father tries to get the brothers to rehabilitate their relationship, but Roderick is also repulsed by Chester’s inability to let life bring him down.

The competition begins with Siam vs. Mexico, as they battle on stage in front of the only judge, Lady Port-Huntly. Much like Best in Show, we are treated with constant commentary from a pair of announcers. They deliver the best set of lines that made me forgive the horrendously out-of-tune set of strings sawing out Mexico’s song.

“The singers are giving us a sad peek into child burial customs down Mexico way.”

“The Mexican mama is being very firm with her dead infant. ”Now go away,“ she wails, ”You are dead. Don’t sneak in at night to nurse from my breast. That milk is only for the living.“ To Canadian ears, that may sound harsh.”

“Well, I guess dead children, like any other kind, have got to learn.”

The winners of this and all subsequent rounds are rewarded with a plunge into an above-ground pool filled with Muskeg beer.

Chester, after viewing how stiff the competition is, wanders the city with Narcissa to brainstorm ideas for their act, while simultaneously bribing previous competitors to forfeit their place and join Team America. His approach to sadness is purely corporate, as all hardship he’s experienced in his own life has failed to make an impact. As he reiterates time and time again, he’d rather have horrible things happen to him than be bored.

When Canada vs. America finally commences, Chester’s exploitation of enslaved people’s sadness wins them the victory while Canada is knocked out. Roderick goes into a tailspin when he recognizes Narcissa’s voice as his long lost wife, and is further distressed when he realizes she doesn’t remember him and is incidentally screwing his brother. Roderick finally confronts Narcissa after he discovers she’s turned his melancholy theme song into an upbeat banger, and they sleep together because she’s a nympho that feels bad for him. Even after penetration she doesn’t remember their dead son, and seems unwilling to relive that part of her life. The jar Roderick carries around of his dead son’s heart pickled in Roderick’s own tears is symbolically shattered as he descends further into madness.

Meanwhile, Chester and Helen rekindle their romance, to the chagrin of his father. To get back into Lady Port-Huntly’s good graces, Chester’s father manufactures her a pair of glass legs filled with Muskeg beer to replace the ones he sawed off. While she is thrilled with the gift, she doesn’t forgive the former doctor for butchering her. Devastated by her rejection, he gets blackout drunk and falls through a skylight into a pool of beer and drowns.

America and Serbia continue to knock out other countries, until they inevitably face-off against each other. Even though she is a judge, Lady Port-Huntly joins Team America to perform in the final showdown and show-off her beer-filled appendages. Roderick finally plays his rendition of “The Song is You”, which not only returns Narcissa’s memories, but shatters Helen’s glass legs. Lady Port-Huntly responds to Chester’s glib indifference to her new-found misery by stabbing him with the shards. He then sets the brewery on fire with his cigar. Almost everyone started this movie sad, and in the end, everyone ends up dead.

The songs in The Saddest Music in the World are great, and I really appreciated the stylized way it was filed and edited. It’s a unique experience, and it’s unfortunate it wasn’t my type of humor. I watched this movie three times in an attempt to give it a fair shake, because upon first viewing I actively hated it. It was probably the fastest I knew I wouldn’t like a movie. In the opening scene some smug dude is getting a hand job in front of a fortune teller while having flashbacks of his mother’s death. She just drops dead right in front of him and then he comes. Like, OK, it’s gonna be one of those… That said, this is an extremely well-made film, and if any of the above intrigues you, please check it out.