Billingslea was born in Charleston, South Carolina. His father was from Macon, Georgia and his mother was from Malensis, South Carolina near Charleston. His family moved to Meriden, Connecticut, where he grew up. At Maloney High School, he lettered in football, basketball, and baseball, and was offered a contract with the Kansas City Athletics, but at the advice of his father, went to University of Connecticut, where he played football and co-captained in his senior year. He graduated with a Bachelor's in Political Science in 1966. He was involved in ROTC and had to turn down entering the NFL in order to fulfill his military Service, however, his commitment was deferred so that he could attend UConn Law School, where he graduated and passed the Connecticut bar in 1969. He became an officer in the Army's Judge Advocate General's Corps, and had tours in Germany and Europe, working on a number of cases. In Germany, he also taught Criminal law for the University of Maryland's extension program.