Simon Benjamin is only 27, but he has already had several careers. At age 14, inspired by Sean Henry, a T-shirt and poster artist in his hometown of Kingston, Jamaica, Benjamin began airbrushing and stenciling T-shirts and banners. “I guess I was designing and didn’t even really realize it,” he recalls. What started as a pastime evolved into a vocation, and he started selling his creations; six years later, he began working as Henry’s assistant. “That was the first time I realized you could make money designing,” Benjamin says. “In Jamaica, there are not many people doing design in an interesting way who are making a living off of it.”
Benjamin relied on his entrepreneurial instincts again after graduating from college with a bachelor’s degree in business management (and a minor in international relations); he became a party promoter, organizing dance events in Kingston for which he also designed flyers and posters. Though successful as a self-taught designer, he yearned for a more formal education. So, in 2001, he started a bachelor’s degree course in graphic design (with a focus on motion graphics) at the School of Visual Arts in New York.
Benjamin is now a designer/animator at the New York–based design outfit Freestyle Collective. The tall, soft-spoken Benjamin has worked on station IDs for Comedy Central, Fuel TV, and BET, as well as in-store promos for Rockport shoes. His projects—an animated reverie for Fuel TV showing fish, ocean, and waves that turn out to be the daydream of a surfer stuck in traffic; a montage of silhouetted jazz iconography for BET—are compelling but hard to pin down to one aesthetic. “My style ranges from drawing cartoons to drawing people in a semi-realistic way, but it’s always fairly loose,” he says. To maintain that quality, he incorporates hand-drawn elements when he can: “I like to put my hand in there. That’s where I’m coming from, a drawing background.”
One can discern Benjamin’s roots in his personal projects. In “e.e. cummings vs. Kingston,” a project he began as a student at SVA, he layers hand-drawn illustration, archival newspaper photography, text, and ani-mation to create a poignant lamentation about a time in the ’70s when political strife in Jamaica erupted into violence. “I wanted to do something about Jamaica that people don’t really associate with it,” he maintains, noting that outsiders always link the country to Rastafarianism and reggae. “I wanted to do something else.”
The restlessly creative Benjamin—he has lately taken up photography and directed a music video—professes a deep admiration for filmmaker Michel Gondry; there is something in Benjamin’s loose style that is reminiscent of Gondry’s use of the rough-hewn and hand-made to conjure flights into worlds of the imagination. Part of the charm of this approach, of course, is in acknowledging that no creation will ever be flawless. “Embracing the mistakes makes things more interesting,” Benjamin says. “I’m not into things looking perfect and having perfect symmetry.”