After graduation from college in 1974, Wilcutt taught high school math for two year prior to entering the Marine Corps. He was commissioned in 1976 and earned his wings in 1978. Following initial F- 4 Phantom training, he reported to Kaneohe, Hawaii. While assigned to VMFA-235, he attended the Naval Fighter Weapons School (Topgun) and made two overseas deployments to Japan, Korea, and the Philippines. In 1983, he was selected for F/A-18 conversion training and served as an F/A-18 Fighter Weapons and Air Combat Maneuvering Instructor in Lemoore, Cal. In 1986, Wilcutt was selected to attend the United States Naval Test Pilot School, where he earned the title “Distinguished Graduate.” Following graduation, he was assigned as a test pilot/project officer for Strike Aircraft Test Directorate at Patuxent River, Md. There he flew the F/A-18 Hornet, the A-7 Corsair II, the F-4 Phantom and various other aircraft to test a wide variety of projects and classified programs. He has over 4,400 flight hours in more than 30 different aircraft.

Selected by NASA in January 1990, Wilcutt became an astronaut in July 1991. Technical assignments to date include work on Space Shuttle Main Engine and External Tank issues; Astronaut Support Personnel team at the Kennedy Space Center, supporting Shuttle launches and landings; technical issues for the Astronaut Office Operations Development Branch; NASA Director of Operations at the Yuri Gagarin Cosmonaut Training Center, Star City, Russia; and Chief of the Astronaut Office Shuttle Operations Branch. He was the pilot on the Shuttle Endeavour (STS-68) in 1994 and Atlantis (STS-79) in 1996, and was the mission commander on Endeavour (STS-89) in 1998 and Atlantis (STS-106) in 2000. A veteran of four space flights, Wilcutt has logged over 1,007 hours in space.