He was also educated at the prestigious Loomis Chaffee prep school in Windsor, Connecticut, and began a career building original custom log homes in North Carolina.
His career then took a major upswing as he was assigned the roles of Lieutenant Lockhart in Stanley Kubrick's Full Metal Jacket (1987) and Felix Leiter in the James Bond film The Living Daylights (1987).
He later played a recurring role in season two of Fox's real-time thriller 24, as Bob Warner, the father of both the love interest of hero Jack Bauer and of another daughter whose fiancé is suspected of being a terrorist.
Terry reprised his role as Shephard on several occasions in flashbacks before appearing frequently in real time on the island as an incarnation of "the man in black".
He had a guest role in a 2006 episode of Law & Order, as well as the part of older Jacob Wheeler in Steven Spielberg's Into the West mini series, which was nominated for 16 Emmy Awards in 2006.