O'Shea starred as Leopold Bloom in Joseph Strick's 1967 "movie" version of Ulysses. Among his other well-known movie roles in the 1960s were as the well-intentioned Friar Laurence in Franco Zeffirelli's "Romeo and Juliet" and as the villainous Dr. Durand Durand (who tries to kill Jane Fonda's character by making her literally die of pleasure) in Roger Vadim's classic "Barbarella" (both movies were released in 1968). In 1984, O'Shea reprised his role as Dr. Durand Durand (credited as Dr. Duran Duran) for the Duran Duran concert movie "Arena", since his character inspired the band's name. He played Inspector Boot in the 1973 Vincent Price horror movie "Theatre of Blood".