Did Walter Matthau ever direct a movie? July 14, 2020 by Pamela Landy Walter Matthau directed only one movie, Gangster Story (1959). He both directed and starred in it. Related Answers In how many movies did Humphrey Bogart, Mary Astor, and Sydney Greenstreet star together? Where were the following situation comedies set? Did Alfred Hitchcock ever direct a costume drama? Did Fritz Lang ever direct a Western? How many films did John Wayne direct? How long was Walter Cronkite a television anchorman for CBS?