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Chief retainer of Ako Domain, he loyally served his lord Asano Naganori. In 1701 Asano attacked the protocol official Kira Yoshinaka in the corridors of Edo Castle; the shogunate ordered Asano to commit seppuku that same day and abolished the domain. Outraged by this one-sided verdict, Oishi vowed revenge. He spent roughly a year and a half feigning a dissolute lifestyle in Kyoto's Yamashina district and Osaka's Ichiriki teahouse to lower Kira's guard, enduring the contempt of being called a 'daylight lamp'—dim and useless—while steadily preparing for the raid and preventing defections among his comrades. On the night of December 14, 1702, he led 47 ronin in a raid on Kira's mansion in Honjo and accomplished their sworn purpose. The following year the shogunate ordered all 47 to commit seppuku; they were buried alongside their lord at Sengakuji Temple in Takanawa. Their act was lauded as the pinnacle of bushido and has been retold as 'Chushingura' in countless kabuki plays, films, and television dramas ever since. A memorial festival is held at Sengakuji every year on December 14.

A patient and far-sighted strategist. His ability to maintain a facade of debauchery for nearly two years to deceive enemies was remarkable. An excellent leader who united 47 comrades in purpose.

The Ako Incident became "Chushingura," depicted countless times in kabuki, film, and drama, symbolizing Japanese ideals of loyalty. A memorial festival is held annually at Sengakuji Temple on December 14.