In 1971, he played the by-the-book mayor of San Francisco, perpetually frustrated by Clint Eastwood, in the first Dirty Harry movie. He later parodied this role in the premiere episode of Sledge Hammer! and One More Train to Rob. In 1972 he appeared as a villain in the Fear Is the Key. In 1973 he appeared in Charley Varrick.. In 1974 he co starred in the film The Black Windmill with Michael Caine and Donald Pleasence. Also in 1974, he appeared in The Questor Tapes. In 1975, he starred in Brannigan, alongside John Wayne and Richard Attenborough. In 1976, he played Fletcher in Eastwood's The Outlaw Josey Wales.