Unlucky is written by Chris McCawley, who is a friend of a friend of Robertson’s. Knowing that Robertson is a commercial film director, represented by Holiday Films in Toronto, McCawley asked him to take a look at the script for his feedback and notes. The two met, discussed the film and McCawley asked Robertson to direct it. Unlucky’s lead character, Darren Mackintosh, who is played by actor Jim Annan, is completely engaging and endearing throughout the film. “Casting was a lot of fun,” says Robertson. “Michael Stevenson, who is one of my favourite casting directors, organized everything. We were very lucky to have so many actors interested in the project that we were almost spoiled for choices. Jim Annan was just perfect for the lead role and we were all so impressed when he walked in and read for us. He was the first guy who came in and we loved him. And he held up, even after seeing almost 60 other actors for the role. He was a unanimous choice for the producers and myself.” There are many scenes in the film where Annan appears naked outdoors in Toronto. When asked about the shooting these scenes Robertson explains, “Jim was a real trooper. We filmed him naked for several mornings. It was pretty cold running around the city at 5am. I think Jim started to dread whenever I would ask him if we could swing by and pick him up early the next morning for a few naked running shots. We would be driving around the city on our way to a naked shot and I would see a great alley and get everybody out to shoot a shot.” There was recently a cast and crew screening for Unlucky in Toronto. When asked what it was like to see the film finally completed and played on a big screen, Robertson says “It was pretty stressful until I heard that first big round of laughter. It was pretty funny because even though I had been watching the film in various forms for almost nine months, once I was watching it on the big screen I became totally engrossed in the film, as if I didn’t know how it was going to end.” Although Robertson’s commercial film work is very visual, Unlucky takes him in completely another direction with its comedic-driven narrative. “Going from short format to long was weird because you start to think about how best to tell the story, and if it takes 20 seconds or 10 minutes it doesn’t matter because your just making sure that it helps move the story along,” says Robertson. “Whenever I get a script, commercial or otherwise, I’m always looking for the best solution to execute it. So when I looked at the script for Unlucky, my brain just started to figure out how to execute it in the most compelling way. I just saw the film in my head.” A little trivia on the film: one of the locations, the mansion of the lottery winner, was actually the house that belonged to Prince when he lived in Toronto. “There’s a party room in the basement that was completely purple. Floor to ceiling. Even the felt on the pool tables.” Says Robertson.