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Millionaire grew up in and around the seaside town of Gloucester, Massachusetts. He came from a family of artists – his father was a commercial illustrator, his mother and grandparents were painters – and was encouraged to draw from an early age. His grandfather, who was a friend of the cartoonist Roy Crane, had a large collection of old Sunday comics which were an early source of inspiration to Millionaire. He drew his first comic strip, “about an egg-shaped superhero who flew around talking about how great he was and then crashing into a cliff,” when he was nine years old. At age 13 he lost his natural front teeth in a car accident; since then he has worn false teeth. During high school Millionaire continued to draw comic strips for his own amusement.