"Try harder," are the two words of avuncular philosophy I remembered most about Deco Dawson, before moving to Winnipeg in 2005.

I met Deco at the 2003 Chicago Underground Film Festival where he was, in fact, given the key to my south-side bungalow's attic-cum-penthouse, and where his star in independent film circles had garnered the lambency of a Die Maschine strobe light. Deco was in town to premiere five short films - his trio of Royal Art Lodge collabs, along with Fever of the Western Nile and Defile in Veil (the last of which had won a CUFF post-production award) - and I was bugging him to give me an inkling of advice as to how to become as prolific, successful and sought-after an 'experimental' (a term Deco loathes) filmmaker as he.

Dawson's words were seared into my brain with all the self-flagellating intensity of a hot poker - nearly the same as the infamous self-branding performance piece, L'execution du testament du marquis de Sade, performed by Canadian Surrealist Jean Benoît in 1959 and re-enacted in Dawson's forthcoming bio-doc of the artist, Ne Crâne Pas, Sois Modeste.

A sneak peak of that work-in-progress will be featured at this weekend's Cinematheque Dawson retrospective, called Dream Sequences, and as I recount my profound souvenir to Deco over a breakfast summit at the Black Sheep Café, he laughs.

"Try harder, yes, but that's not directed to other people. That's directed to me, myself," he says.

Deco's adage seems very obvious, though unhelpfully vague, teetering perhaps on unintended condescension. But as I sip from my coffee IV, I realize that it really encapsulates a lot about the excitingly great filmmaking oeuvre of the 29-year-old wunderkind (once called "the new hearthrob of experimental cinema") seated before me.

By the age of 22, Dawson had already created a handful of enthrallingly oneiric Super 8 shorts and, while auditing a University of Manitoba film class taught by Guy Maddin, had come under the wing of our city's biggest-deal filmmaker, with whom he would go on to edit and co-direct on now-canonical Heart of the World (2000) and Dracula: Pages from a Virgin's Diary (2002). From his accomplishments, it was clear that Deco was no slacker.

"I'm really self-critical and won't release anything if it's not good enough. If it doesn't say something, it's just not good enough," Deco says.

The Cinematheque's retrospective attempts to show most of Dawson's solo oeuvre, divided into two programs: Early Works, and Later Works.

Early Works takes viewers back to Dawson's FILM cycle of hand-edited, optically printed and blown-up, frenetically edited, black-and-white Super 8 films, including: 1998's FILM(luster) and FILM(emend), 1999's FILM(knout), 2000's FILM(lode), and 2001's FILM(dzama) - which won Best Canadian Short Film at the Toronto International Film Festival. The FILMs loosely investigate the theme of obsession, and some even contain contextually revelatory Doppelgänger plots. When FILM(knout)'s Sharon Johnson is aggressively whipped by an evil double of herself, one wonders if Bad Sharon isn't scolding Good Sharon for, well, not trying hard enough.

Early Works concludes with 2003's hand-processed Fever of the Western Nile and the unsatisfyingly odd-man-out Defile In Veil, and is a great testament to the capacity of 'basement filmmaking' to dazzle the eyeballs and brain - in contrast to whatever huge sums of money other filmic entertainers may try to throw up onscreen.

Later Works delves into the present stage of Dawson's career, one where his entire arsenal of silent-film techniques and black-and-white imagery seems to have been decommissioned.

"It was a change in cinematic styles," Dawson says. "At that point, I just abandoned everything I knew about filmmaking - all the black and white, all the Super 8, all the silent stuff. I got rid of it completely and said, 'If I'm gonna be a better filmmaker, I just have to learn more things about filmmaking, such as colour, shooting 16mm, sound and movement.' Even non-editing, where things aren't so cut up, and things can actually tell a narrative story through editing as opposed to relying on shooting things poorly and, in the editing room, compiling. That was a form of 'excuse editing,' and I think Dumb Angel really put me on a different track."

The shift in approach was, inevitably, due in part to the close and suffocating associations some programmers and audiences had come to make between Deco's films and those of Guy Maddin. Once again, Dawson hunkered down and got to work.

"At that point, you're staring your career in the face and it's telling you it's over. It's telling you that everything you've worked for is done, it's gone," Dawson says. "If you continue to make the same kinds of things, after that point, everything you do is only going to be mimicry."

Thankfully, Dawson's accrued reknown translated into screenings and awards at the same important film festivals he had been showcased at before.

"So, actually, it was great because I could have been stuck in that circle. I wanted to do a feature in that old style, but in the five years since there have been four silent, Super 8 features made out of Winnipeg."

Indeed, 2005's Dumb Angel marked an almost Costanza-like oppositional approach to style, with its single 9-minute take - in lavish, fireworks-replete colour - of Inward Eye drummer Anders Erickson bashing the skins inside an ambulance shelter. Although his early FILMs could be considered as surreal Phillip Glass music videos, Dumb Angel officially inserted Dawson into the realm of music video, culminating in his editing of last year's Metric DVD, Live at the Metropolis (a clip of which will also be featured in Later Works).

Later Works is anchored by Dawson's long homage to the history of cinematic styles, The Last Moment (2007), and will hopefully pave the way for his first feature, about the Hungarian cinematic inventor Paul Fejos, currently in development.

"The feature's been in the works for quite a while," Dawson says. "The Last Moment was my way of bridging that gap between the super-indie, self-financed movies, into something that's visually and cinematically vibrant but requires the production values of a feature."

With a little luck - and this retrospective's tangible body of evidence - here's hoping that the notoriously bureaucratic Telefilm will soon give Dawson the chance to attempt a showcase of his skill set at feature-lengths.

Walter Forsberg is a filmmaker with l'Atelier national du Manitoba.