Only 11 years old when he notched his first hit single, Billy Gilman was the youngest performer ever to reach the Billboard country charts, breaking a record held by Brenda Lee since 1957. Gilman was born in Westerly, RI, on May 24, 1988, and grew up in nearby Hope Valley. He was singing before he started school and developed rapidly enough to start performing publicly at age seven. He was booked as an opening act at several county fairs, including one with headliner Jo Dee Messina. Gilman caught his big break when Asleep at the Wheel leader Ray Benson heard him sing and was impressed by the precocious power behind his vocals. Benson had Gilman make a demo tape, which wound up landing the young singer a deal with Epic.