A native of Evansville, Indiana, LeRoy Smith got his first guitar when he was 11 years old and actually put together his first band when he was in the eighth grade. During his high school years, he continued playing in bands as well as acting in school plays and performing in local talent shows. After high school he got his first break playing in a local nightclub in Evansville. Shortly after he enlisted in the army and began playing for the USO and enlisted and officers clubs.

After his tour of duty, LeRoy returned to Evansville and started his music career by playing the nightclub circuit with his own band. LeRoy began his songwriting, which helped support his decision in 1981 to move to Nashville and to pursue a full-time music and writing career.

Shortly after arriving in Nashville, LeRoy caught the eye of John Denny at Cedarwood Publishing Company, a publishing company founded by Billy Denny, a member of the Country Music Hall of Fame. Bill Rice, another Country Music Hall of Fame member, recruited him to work for Shobie/Swallowfork. LeRoy's songwriting career was moving forward by working with the best writers in the industry for the next four years. Additionally, he performed his own music in some of the top showcase rooms in Nashville, including the world-famous Bluebird Cafe.