When Nazi Germany invaded Poland in 1939, Gene Raymond became convinced that the U.S. would someday be drawn into the war. At his own expense, he took flying lessons to become a pilot, and following the Japanese attack on Pearl Harbor in December 1941, he interrupted his motion picture career and accepted a commission as a first lieutenant. He initially flew as an observer in B-17s on anti-sub patrol off the Atlantic coast. Next, he attended intelligence school, and following graduation, he was sent to England in July 1942 and assigned to the 97th Bomb Group. He was soon promoted to Assistant Operations Officer in the 8th Bomber Command.
In 1943 he returned to the states and flew B-17s, B-25s, B-26s and P-39s. Following the termination of hostilities, he was released from active duty as a major on Oct. 22, 1945.
Raymond remained in the USAF Reserve following World War II. On Aug. 13, 1968, after having logged more than 5,000 hours and having been awarded his command pilot wings, he retired from the USAF Reserve as a colonel.