Hillin made his debut in NASCAR Winston Cup Series competition at the age of 17, driving a car owned and sponsored by his family and crewed by Harry Hyde in the 1982 Northwestern Bank 400 at North Wilkesboro Speedway to a 21st-place finish. Hillin moved to North Carolina to further his career, continuing his education through correspondence courses; he graduated from high school the day before the 1983 Coca-Cola World 600; in 1984 he joined Stavola Brothers Racing, and in 1986 became the youngest winner in NASCAR's "modern era" when he won the Talladega 500 for the team, at the age of 22 years, 1 month and 22 days.