Lester was born in the United States to American parents in Indianapolis, Indiana. Terry, who had an interest in the film industry since a young age, loved to watch celebrities in their roles. He finished his high school education at Southport High School.
Lester then began his acting career professionally with primetime TV guest roles while attending DePauw University. In addition, he appeared in musical theaters and performed in concerts. He began his career with an uncredited role as Mr. Kelly in the 1975 film Airport 1975.
