Billingslea was born in Charleston, South Carolina. His mother was from Malensis, South Carolina, near Charleston, and his father was from Macon, Georgia. 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.

Billingslea lives in the Los Angeles area. He is married to Cecelia Billingslea; they have a son and a daughter together. In 1987, Billingslea was inducted into the Meriden Hall of Fame. In 2014, he gave the keynote address at a UConn Law School reunion.

While in college, Billingslea was encouraged by his fraternity brother to perform the lead role in a production of The Emperor Jones. This inspired him to go into acting, and he started getting involved professionally while he was in law school. After moving to Los Angeles, he was involved in a number of action shows, including TJ Hooker, Hunter, The Fall Guy and The A-Team. Billingslea mentioned in an interview that it was probably because of his military background that he was often cast as an officer. He portrayed Ezra in the TV miniseries North and South and was involved in a number of shows including Who’s the Boss?, Murphy Brown and Married… with Children. On the Nick series Just Jordan he played Jordan’s maternal grandfather Grant. In the TV sitcom Franklin & Bash he portrayed Judge Douglas. He also acted in films such as Night Shift, The American President, Hannah Montana: The Movie, Halloween H20: 20 Years Later and a remake of The Blob. In 2013, he portrayed Captain Abbot of the Starship Bradbury in the feature film Star Trek Into Darkness. He continues to act in stage plays such as Driving Miss Daisy where he was nominated for a Los Angeles Ovation Award in 2005.