Since the age of three, Dillard watched church choirs. His Grandma used to stand Little Ricky on top of his baby potty and he would direct and sing. At five years old, he began directing the junior choir at St. Bethel Baptist Church. In 1981 he formed the first gospel choir at Bloom High School. "There were so many church kids there and they liked to sing," he says. "So, I started a group called Ricky Dillard and Company and we sang at school.