- His father, General Richard G. Stilwell, was commander of United Nations forces in Korea and a deputy under secretary of the Department of Defense.
- He served two tours in Vietnam as a rifle company commander, earning a Silver Star and Purple Heart. After tours at West Point and in Korea, he retired in 1985 with the rank of lieutenant colonel.
- Career U.S. Army officer (1965-1985) before he began his acting career.
- Was the son of the late Gen. Richard G. Stilwell, commander of United Nations forces in Korea and deputy under secretary of the Department of Defense.
- Father of Richard Stilwell III and Catherine Stilwell-Lavin.
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