Flying was Underwood's passion, and he obtained his private pilot's license during his teenage years and also held a sailplane rating. After graduation from the University of Kentucky, he joined the Marines. During his flight training, he was selected to fly the AV-8B Harrier. Underwood was then assigned to the Harrier Fleet Replacement Squadron VMAT-203 based at Marine Corps Air Station Cherry Point, NC. On February 27, 1991, Capt. Underwood was part of a 4 ship, flying a combat mission supporting the Marine advance near Safwan, Iraq. During this mission, his AV-8B was hit by a Man-Portable Air-Defense System surface-to-air missile. His Harrier crashed, and he was killed. Capt. Underwood was the only Lexington Native killed during Operation Desert Storm.

Capt. Underwood was survived by his wife, Donda, and a 5-month-old girl, Anne, whom he never was able to meet. His widow, Donda Hill Rhodes, said, “He said he would fly even if he were not paid for it. It was his passion. The Harrier was a challenge, and you could not fly it unless you were at the top of your class. His devotion to duty and ties to his Kentucky home, specifically Lexington, led to the local Young Marines Unit being named in his honor. Captain Reginald "Woody" Underwood, USMC had his love, passion, and dedication to Aviation, his Service to his Country, and his continued Service (after his death) to inspire young generations to Serve.