Hill is also known for directing such films as The World of Henry Orient (1964), Hawaii (1966), Thoroughly Modern Millie (1967), Slaughterhouse-Five (1972), The Great Waldo Pepper (1975), Slap Shot (1977), A Little Romance (1979), The World According to Garp (1982) and his final film Funny Farm (1988). According to one obituary "few directors achieved such fame and success... even fewer enjoyed such eminence for such a short period of time."
He was born in Minneapolis, Minnesota, to George Roy and Helen Frances (née Owens) Hill, part of a well-to-do Roman Catholic family with interests in the newspaper business; the family owned the Minneapolis Tribune. Hill was no relation to George W. Hill, director and cinematographer of numerous silent movies and early sound films in the 1920s and early 1930s. He was educated at The Blake School, one of Minnesota's most prestigious private schools, and at Yale University, class of 1943.
He had a love of flying. After school he liked to visit the airport, and his hobby was to memorize the records of World War I flying aces. He idolized pilot Speed Holman, who, Hill once explained, "used to make his approach to the spectators at state fairs flying past the grandstand upside down." Hill obtained his pilot's license at the age of sixteen. Airplanes featured prominently in his later films and are frequently crashed as well — in Slaughterhouse-Five, The World According to Garp and especially The Great Waldo Pepper which showed the influence on Hill of pilots like Speed Holman.

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