Resorting to desperate measures Jerome marshals his most trusted friends, including a potential love interest, Keisha, played by Shamilla Miller, to attempt a bank heist in order to save his father’s legacy. The Umbrella Men is a riotous blast that has a thing or two to say about community, legacy, and the complicated bonds between parents and their offspring.

Leading the ensemble cast of this unique and colorful romp through Cape Town’s culture-rich Bo Kaap community is De Silva whose Jerome grows from a listless young man existing in his father’s considerable shadow to a leader who is able to inspire confidence, hope and loyalty from within his troupe. De Silva, best known for his work on the television series 7de Laan and in the film, The Last Fight, tells OkayAfrica he connected to the character through Jerome’s relationship with his father. “The idea of having a dad who has a name and a legacy and a community and belongs not to you, but to the world. And then this need of wanting to make a name for oneself. What I like to do is see first what the director gets for free by casting me before we add on the extra layers,” he says.

For Miller (Dead Places, Blood & Water), who plays the female lead, Keisha, it was important that the character be more than a regular love interest. Recognizing some of herself in the character’s independence, Miller talked through several drafts of the screenplay with the director, until a more fleshed out profile emerged. “Between John and I, we both decided to play her quite strong and not just as the love interest. Her role in the story is also unique. John and I had a lot of exchanges, and we did speak about making her a go-getter by connecting her to the larger picture. Keisha is a game player, and she gets very involved.”

The Umbrella Men is very much steeped in Cape Town culture, specifically that of the Cape Malay community, which traces its origins back to Indonesia (at that time known as the Dutch East Indies), and other Southeast Asian countries. They were transported to South Africa as slaves by the Dutch East India Company. The film celebrates the beauty, character and resilience of the indigenous group of people known as Cape Coloreds, and this celebration is boldly legible in the look and style of the film. From the the language to the music, the art design and the visual language, The Umbrella Men is true to the point of view of the community that it upholds.

De Silva says this film represents a refreshing break from the norm. “When you are a minority group, the feeling is often that of being overlooked. There are also the stereotypes. When you see us in stories, we tend to be the gangsters and the drug dealers, and that hasn’t changed from apartheid to free society, which is why the film is so important and powerful for us.”

Miller is excited for how The Umbrella Men captures the authenticity in things as simple as speech and the deployment of humor. “We come from a sense of struggle and heaviness but there is lightness and story and happiness, and we don’t always see that,” she says.

The Umbrella Men has been at least fourteen years in the making. Within that space of time, as Barker, who co-wrote the screenplay with Philip Roberts and Lev David, raced to come up with the resources, the project went through different performers until it landed on De Silva and Miller.

At the time De Silva was first approached, comedian Trevor Noah was circling the lead role but was eventually unable to commit. Barker went to see a one-man theater show that De Silva was involved in and became convinced he had found his new leading man. There were still obstacles to cross; De Silva thought this early contact a bit ridiculous but sent his work anyway. He heard nothing for a few years until mid to late-2020 when he got the audition brief. There was a period of silence again until last year when he was called to do a chemistry read with Miller who had been attached to the project for some time as well.

Miller and Barker had met at a directing workshop for actors. After reading the script and committing to the project, Miller entered the waiting game as well, as there would be months of radio silence interrupted only by updates on the development process from Barker. It wasn’t until about three years after they had met that they were ultimately able to make the film.

Even though both actors had met a couple years back while working on a commercial and knew of each other’s work, Miller and De Silva were far from friends. But for the chemistry read, they had to convince the director that they would be believable on screen considering that so much of the film depends on their sizzling relationship.

It worked, and The Umbrella Men makes its international premiere at the Toronto International Film Festival (TIFF) this week, and both De Silva and Miller consider it the privilege of their lives to be able to bring this culturally specific slice of South African living to a global audience and have them identify with the colors and freewheeling energy of the Bo Kaap community. “To be the face of this introduction to Cape Town and the Bo Kaap community is just awesome,” says De Silva. “As a Colored community, we have a lot to be proud of and here we are representing on an international stage.”