He appeared as the mild-mannered and good-natured POW forger Colin Blythe in the film The Great Escape (1963), who discovers that he is slowly going blind, but nonetheless participates in the mass break-out, only to be shot down by German soldiers because he is unable to see them. Variety highlighted Pleasence and Richard Attenborough as giving some of the better performances in the film, Pleasence specifically being praised for having the most moving portrayal and depicting "the film’s most touching character." In The Night of the Generals (1967), he played another uncharacteristically sympathetic role, this time as an old-school German general involved in a plot to kill Adolf Hitler. In 1971, he returned to the realm of the deranged, delivering a tour de force performance in the role of an alcoholic Australian doctor in Ted Kotcheff's nightmarish outback drama Wake in Fright.
