His father served as Army Surgeon and died from an accidental gunshot wound, while stationed as Major and Chief of the sanitation work at Camp Meade, Maryland, in August 1917.

Young Charles followed in his father's footsteps and completed the Army preparatory school at Fort McPherson, Georgia and received an appointment to the United States Military Academy (USMA) at West Point, New York, in June 1932.

[3][4] Following the establishment of Army Airborne School at Fort Benning, Georgia in June 1940, Billingslea was ordered for paratrooper training and earned his wings several months later.

Following the surrender of the Afrika Korps, he assumed duty as Executive officer of Pathfinder battalion of 82nd Airborne Division and took part in Operation Husky, the Allied invasion of Sicily, in July–August 1943.

[3][4] Several weeks later, Billingslea was appointed Executive officer, 504th Parachute Infantry Regiment under Colonel Reuben H. Tucker and participated in the Operation Avalanche, the Allied landings near the port of Salerno in September 1943 and later in the Battle of Anzio in early 1944.

Key officers and men became casualties, but Billingslea moved among the disorganized company, restored command and assumed the initiative in the face of determined resistance from numerous German strongpoints in Katerbosch.

He personally directed the house-to-house reduction of the enemy and his presence in this critical zone inspired officers and men to emulate his conduct in a fight for the town which lasted all day and through the night.

The citation for his DSC reads: The President of the United States of America, authorized by Act of Congress, July 9, 1918, takes pleasure in presenting the Distinguished Service Cross to Colonel (Infantry), [then Lieutenant Colonel] Charles Billingslea (ASN: 0-20367), United States Army, for extraordinary heroism in connection with military operations against an armed enemy while serving as Commanding Officer, 325th Glider Infantry Regiment, 82d Airborne Division, in action against enemy forces on 2–3 October 1944, in the vicinity of Katerbosch, Holland.

Key officers and men became casualties, but Colonel Billingslea moved among the disorganized company, restored command and assumed the initiative in the face if determined resistance from numerous German strongpoints in Katerbosch.

Billingslea was subsequently decorated with a second DSC, the citation for which reads: The President of the United States of America, authorized by Act of Congress, July 9, 1918, takes pleasure in presenting a Bronze Oak Leaf Cluster in lieu of a Second Award of the Distinguished Service Cross to Colonel (Infantry) Charles Billingslea (ASN: 0-20367), United States Army, for extraordinary heroism in connection with military operations against an armed enemy while serving as Commanding Officer, 325th Glider Infantry Regiment, 82d Airborne Division, in action against enemy forces on 2 February 1945, in Germany.

Colonel Billingslea fearlessly exposed himself to intense enemy small arms, mortar, and artillery fire to direct his command's assault against Siegfried Line fortifications.

[2]The 325th Glider Infantry Regiment finished its advance into Germany near Ludwigslust, past the Elbe River and Billingslea was appointed Chief of Staff, 82nd Airborne Division under Major General James M. Gavin on May 7, 1945.

Upon his return stateside, he was attached to the planning staff of the Army Ground Forces at Fort Monroe, Virginia, and was reverted to his peacetime rank of captain on June 12, 1946.

[3][4] In August 1950, Billingslea was assigned to the Office of Operational Research in Washington, D.C., and also saw temporary duty in Korea, where he was involved in the effort to liberate Major General William F. Dean who was taken a prisoner of war following the Battle of Taejon in July 1950.

He was then ordered to Paris and appointed Chief of Plans at Supreme Headquarters Allied Powers Europe (SHAPE) under General Alfred Gruenther, whom he knew from his service with Fifth Army in Italy during World War II.

[3] Billingslea was subsequently promoted to the permanent rank of Colonel and assumed duty as deputy director, European Region, International Security Affairs, Department of Defense at the Pentagon.