This handsome son of actors Sean Connery and Diane Cilento made his own bid for respect as an actor playing "Macbeth" in a 1997 remake of the Shakespearean classic. Prior to that, the suave blond Jason Connery, whose features combine those of both his famous parents, had often been cast in dashing, sometimes heroic, leading roles. He began his career playing a cadet at a Southern military academy in "The Lords of Discipline" (1983), but had his first lead in "The Boy Who Had Everything" (1985), as a university student who has problems with his mother (played by Cilento), his girlfriend, and life. The film did not make Connery "box office" and it was three years before he again appeared in feature films, then in little seen efforts such as "Bye Bye Baby" and "Puss in Boots". Better roles came in the 90s, although not necessarily in films with widespread American distribution and Connery has remained an unknown quantity in Hollywood. In 1994, he was a German geologist who flees to Southwest Africa to avoid military service in "The Sheltering Desert".

The small screen has given Connery more of a following, especially for his work (from 1985-1986) as "Robin of Sherwood", an updating of the Robin Hood story that aired in the USA on Showtime. He was featured as a self-satisfied athlete in "The First Olympics: Athens 1896" (NBC, 1984) and had one of his best roles as the writer of the James Bond stories (which ironically had made Connery's father famous) in "The Secret Life of Ian Fleming" (TNT, 1990). More recently, he co-starred with his father's close friend Michael Caine (who was reprising his feature role of spy Harry Palmer" in "Bullet to Beijing" (The Movie Channel, 1995) and (The Movie Channel, 1998).