Maddin's core group of friends from this period, who played various roles in the production of his early film projects, were known as "the Drones" and included Harvie, Ian Handford, and Kyle McCulloch (now a writer for South Park).

[12] Maddin joined the Winnipeg Film Group around this time, and also became friends with producer Greg Klymkiw, with whom he began making a cable access television show, Survival (c. 1985–87).

At the festival Maddin met Atom Egoyan, Jeremy Podeswa, Norman Jewison, and began to form connections with Canadian filmmakers across the national scene.

Kyle McCulloch starred in the film as Einar, a lonely fisherman who contracts smallpox and begins to compete with another patient, Gunnar (played by Michael Gottli) for the attention of the young nurses.

Having proven himself as a filmmaker and established a reputation outside of Canada, Maddin began work on a series of feature films produced on larger budgets and more traditional production schedules and processes.

Maddin's third feature, Careful (1992), was styled after another early cinema genre, the German mountain picture (or Bergfilm) — a surprising choice, given that (as filmmaker Caelum Vatnsdal has noted), "Winnipeg's highest peak is, in fact, an artificial hill that had been created by laying sod over a garbage dump.

[12] Careful, also cowritten by George Toles, is set in the mountain town of Tolzbad, where the townspeople are forced to repress their behaviour pathologically, since the slightest expression of emotion can trigger a devastating avalanche.

Careful premiered at the New York Film Festival and, although it was not a commercial success elsewhere, "single-handedly saved a struggling art-house cinema in Missoula, Montana" where "sell-out crowds had filled the house twice every night for two weeks".

He met with Claudia Lewis, who worked for Fox Searchlight, but Maddin found himself dispirited with the projects he was offered: "I remember one was a love story set in a TB sanatorium.

As seen in Noam Gonick's documentary Waiting for Twilight, Maddin was dissatisfied with the film-making process due to such creative interference from his producers, saying "just close the mausoleum lid on me" since he was possibly done making films.

Maddin then wrote and shot The Heart of the World (2000) in the style of Russian constructivism, taking the commission at its literal face value, as a call to produce a propaganda film.

The plot of The Heart of the World concerns two brothers, Osip and Nikolai, who compete for the love of the same woman: Anna, a state scientist studying Earth's core.

Maddin and cowriter Toles based the film on an original screenplay written by Booker Prize-winning novelist Kazuo Ishiguro, from which they kept "the title, the premise and the contest – to determine which country's music was the saddest" but otherwise re-wrote.

Chester Kent (McKinney), a failed Broadway producer, returns home to Winnipeg and competes with his father Fyodor (Fox) and brother Roderick (McMillan) to win the contest and its $25,000 prize.

[30] Cowards Bend the Knee concerns the murderous exploits of a young "Guy Maddin" (played by Darcy Fehr), a hockey player whose forgets his beloved as she dies through complications during an illegal abortion.

[1] The plot concerns "Guy Maddin" (played by Erik Steffen Maahs as an adult, and Sullivan Brown as a child), whose domineering mother runs a lighthouse orphanage on an island where she and her husband perform scientific experiments upon the children in an effort to extend her youth.

Maddin rents out his former home and hires actors to play his family (including Ann Savage as his mother) in the recreation of pivotal scenes from his memories of youth.

The film was cowritten by Maddin and Toles and also stars Udo Kier, Brooke Palsson, David Wontner, Louis Negin, and Kevin McDonald from the comedy troupe Kids in the Hall.

[29] The exhibition premiered at the 42nd International Film Festival Rotterdam from January 22 to February 2, 2003, where the catalogue described it as "A firstofitskind, tenpart peephole installation jampacked with enough kinetically photographed action to seem like a neverending cliffhanger.

"[62] Each six-minute film is viewed through a peephole and together present a fictionalised autobiography, whose main character (named "Guy Maddin") is embroiled in illegal abortion, murderous intrigue, sexual rivalry, and hockey.

Maddin stated in the press that "I've been literally haunted by the idea that there are these really intriguing titles by some of my favourite filmmakers that I'd never get to see [... and] I told myself years ago that the only way I'd get to see any version of these is if I made the adaptation myself.

The film shoots were open to the public and streamed online, and thereby presented as live art installation projects, during which Maddin, along with the cast and crew, held a séance "invit[ing] the spirit of a lost photoplay to possess them".

In the words of Baerwaldt, the story is a fictional "autobiography [that] features a diabolical plot surrounding a coward on a mission [named Guy Maddin] that resembles a cycle of dark spectacles dressed up as, among other things, lewd seduction, Canadian hockey, murder, amputations, hair design, general mayhem, fetish attractions and heartfelt loss.

Meta and Guy lie in bed, in the midst of a particularly spectacular recital of what could be called THE LIMBO-DANCE OF SELF-PITY --- a verbal choreography performed by lovers who manipulate each other through complicated displays of insincere self-loathing.

[67] Maddin's book contains the film's narration as a main text surrounded by annotations, including outtakes, marginal notes and digressions, production stills, family photos, and miscellaneous material.

The book contains a "Winnipeg Map" by artist Marcel Dzama featuring such fictional attractions as "The Giant Squid of the Red [River]", various poster designs for the film, and short articles about working with Maddin by Andy Smetanka, Darcy Fehr, and Caelum Vatnsdal.

The book contains both new and previously published essays by critics and scholars, including William Beard, Dana Cooley, Donald Masterson, David L. Pike, Steven Shaviro, Will Straw, Saige Walton, and others.

[12] Darren Wershler, a Canadian avant-garde poet, critic, and full Professor in the Department of English at Concordia University, has published an academic monograph on My Winnipeg.

Through an exploration of the film's major thematic concerns – memory, the cultural archive, and how people and objects circulate through the space of the city – I contend that My Winnipeg is intriguing because it is psychologically and affectively true without being historically accurate.

Maddin has called My Winnipeg a "docu-fantasia" and Wershler similarly points out that the film's "truth" lies somewhere "in the irresolvable tension created by the gap between documentary and melodrama".