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Robert Downey Sr. is best known for directing the satirical film "Putney Swope" (1969). The film follows an advertising executive who is accidentally elected chairman of a major corporation and uses his position to challenge racial and social norms. "Putney Swope" is considered a groundbreaking work in the New Hollywood movement of the late 1960s and early 1970s, known for its unconventional storytelling and social commentary.