He began his filmmaking career as a pioneer of Japanese experimental films[3][4] before transitioning to directing more mainstream media, and his resulting filmography as a director spanned almost 60 years.

[6] After his father, a doctor,[5] was called to the battlefront during World War II, he was raised in his early infancy by his maternal grandparents.

Through his childhood and adolescence, Obayashi followed many artistic pursuits, including drawing, writing, playing the piano, and possessed a growing interest in animation and film.

[12] Along with works by other filmmakers such as Shuji Terayama and Donald Richie, Obayashi's films would develop the tone of Japanese experimental cinema through the 1960s.

In the 1970s he began a series of Japanese ads featuring well-known western stars such as Kirk Douglas, Charles Bronson and Catherine Deneuve.

[3][16] The film employed a mixture of trick photography and avant-garde techniques to achieve its distinctive, surreal visuals, and has gone on to be considered a cult classic.

He directed a number of coming-of-age films such as I Are You, You Am Me (1982), The Girl Who Leapt Through Time (1983), and Lonely Heart (1985)—which together form his "Onomichi trilogy", named after the town where he was born[10][19]—as well as Chizuko's Younger Sister (1991).