[3][4] Massie won a BAFTA Award in 1959 for Most Promising Newcomer for his role in the Anthony Asquith movie Orders to Kill (1958) in which he played an American bomber pilot in Nazi-occupied France.

[3][5] Also in 1958 he acted in the Peter Hall production of Tennessee Williams' play Cat on a Hot Tin Roof at the Comedy Theatre in London, with Kim Stanley and Leo McKern also in the cast.

[6] Unusually, he played Jekyll in make-up as an older bearded man, and his villainous counterpart Hyde as his young, handsome self.

[7] He also appeared in the thriller movie Sapphire (1959), and The Rebel (1961), featuring British comedian Tony Hancock, as a young actor.

[11][circular reference] Later Massie changed his career to teaching, and became a member of the faculty at the University of South Florida in Tampa, where he had often been a guest artist-instructor over the years, first appearing in a 1966 production of Tartuffe.