Nakadai grew up in a very poor family and was unable to afford a university education, prompting him to take up acting. He picked up a liking of Broadway musicals, and travelled once a year to New York City to watch them[citation needed]. Nakadai was working as a shop clerk in Tokyo before a chance encounter with director Masaki Kobayashi led to him being cast in the film The Thick Walled Room. The following year, he made a brief and uncredited cameo in Akira Kurosawa's Seven Samurai where he is seen for a few seconds as a samurai walking through town.[2] Nakadai's role in Seven Samurai was technically his debut as The Thick-Walled Room's release was delayed for three years due to controversial subject matter. His major breakthrough as an actor came when he was given the part of Jo, a young yakuza in Black River, another film directed by Kobayashi. Nakadai continued to work with Kobayashi into the 1960s and won his first Blue Ribbon Award for his role in Harakiri (his personal favorite among his own films) as the aging rōnin Hanshiro Tsugumo.
Nakadai appeared in two more Kurosawa films from the 1980s. In Kagemusha Nakadai plays both the titular thief turned body-double and the famous daimyōTakeda Shingen whom the thief is tasked with impersonating. This dual role helped him win his second Blue Ribbon Award for Best Actor. In Ran Nakadai plays another daimyo, Hidetora Ichimonji (loosely based on King Lear from Shakespeare's play King Lear and inspired by the historical daimyoMōri Motonari).