[5] After graduating from Kyoto University in 1954, where he studied political history,[6] Ōshima was hired by film production company Shochiku Ltd. and quickly progressed to directing his own movies, making his debut feature A Town of Love and Hope in 1959.

Ōshima's cinematic career and influence developed very swiftly,[7] and such films as Cruel Story of Youth, The Sun's Burial and Night and Fog in Japan followed in 1960.

Despite the controversy, Night and Fog in Japan placed tenth in that year's Kinema Jumpo's best-films poll of Japanese critics, and it has subsequently amassed considerable acclaim abroad.

[8] In 1961 Ōshima directed The Catch, based on a novella by Kenzaburō Ōe about the relationship between a wartime Japanese village and a captured African American serviceman.

[12] Death By Hanging inaugurated a string of films (continuing through 1976's In the Realm of the Senses) that clarified a number of Ōshima's key themes, most notably a need to question social constraints, and to similarly deconstruct received political doctrines.

[13] Months later, Diary of a Shinjuku Thief unites a number of Ōshima's thematic concerns within a dense, collage-style presentation.

Yokoo Tadanori, an artist who created many of the iconic theatre posters during the 1960s and '70s, plays the thief, who gets a bit part in Kara's performance.

[17][18] In 1983 Ōshima had a critical success with Merry Christmas, Mr. Lawrence, a film partly in English and set in a wartime Japanese prison camp, and featuring rock star David Bowie and musician Ryuichi Sakamoto, alongside Takeshi Kitano.

[19] Max, Mon Amour (1986), written with Luis Buñuel's frequent collaborator Jean-Claude Carrière, was a comedy about a diplomat's wife (Charlotte Rampling) whose love affair with a chimpanzee is quietly incorporated into an eminently civilised ménage à trois.

[24] In 1996 Ōshima suffered a stroke, but he recovered enough to return to directing in 1999 with the samurai film Taboo (Gohatto), set during the bakumatsu era and starring Merry Christmas, Mr. Lawrence actor Takeshi Kitano.

Ōshima had initially planned to create a biopic entitled Hollywood Zen based on the life of Issei actor Sessue Hayakawa.

The script had been allegedly completed and set to film in Los Angeles, but due to constant delays, declining health, and Ōshima's eventual death in 2013 (see below), the project went unrealized.

From one film to the next, he would frequently shuffle between black-and-white and color, between academy ratio and widescreen, between long takes and fragmented cutting, and between formally composed images and a cinéma vérité style.