From the age of five, Barry spent three years traveling with his family to places like Fiji, Tahiti and New Zealand on a boat which they built themselves in their own backyard. Barry's mother enrolled him in ballet classes to round out his love of rugby, football, and baseball. At one point, he taught breakdancing. In 1988 Barry graduated from Georges P. Vanier Secondary School. In November of 1997 Barry married Cindy Pepper and had a daughter, Annaliese Grace, on June 17, 2000.